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Day Trips in Massachusetts: Hikes, history, ice cream and unofficial hot dog tours

Clockwise from left, a composite of scenes from the Cape, Boston, central and western Massachusetts.
WBUR file photos and Raquel C. Zaldívar
/
New England News Collaborative
Clockwise from left, a composite of scenes from the Cape, Boston, central and western Massachusetts.

'Day Trips in Massachusetts' was written by WBUR and New England Public Media journalists.

For fabulous things to do each week in western Massachusetts, sign up for NEPM’s weekly Culture To Do newsletter. Every Wednesday, you’ll find recommendations for performances, exhibits, festivals and activities.

For wicked sweet tips for how to make life — and weekends — in Greater Boston more fun, sign up for WBUR's Weekender newsletter.


Welcome to the Bay State. Home to Boston, the educational, business and cultural epicenter of New England. The state capital gets a lot of shine from guests, of course, but our tiny commonwealth is jam-packed with wondrous places to visit in and out of the city.

As New England's most populous state, Massachusetts has so much on tap to entertain locals and visitors alike: vibrant history, lively city adventures, beautiful hiking, delicious food, academia galore and quite a bit of idyllic rural charm.

For such a small state, Massachusetts has several parochial personalities and subcultures. We could spend pages and pages describing them all, but instead chose to wrap our highlights into four main regions: eastern Massachusetts, Cape Cod and the Islands, central Massachusetts and western Massachusetts.

No matter where you venture in the state, there are bountiful options to satisfy everyone.

Jump to: Western Mass. | Central Mass. | Eastern Mass. | Cape Code and Islands


Western Massachusetts

Four counties — each with a distinctive vibe — define the cities, towns and rural reaches of western Massachusetts. Travel around Hampden, Hampshire, Franklin and Berkshire counties and you’ll see the geological and human-made wonders of the Connecticut River Valley. You can visit the remnants and reimagined uses of the industrial age — now breweries, housing and modern manufacturing. Art and culture venues are everywhere. Colleges and their students abound, offering many interesting events and institutions only a college town can provide. The music halls of Northampton are storied, as are the summer performances at Tanglewood and Jacob’s Pillow. Generations of farms have thrived and grown produce in the region’s rich soil, now alongside new farmers adding to a dynamic food scene.

While some will continue to debate where western Mass. begins, take our word for it! NEPM is based in Springfield — the state's third-largest city — and covers and broadcasts to the remarkable communities that make up the fabulous 413. Structure a road trip on our historic and scenic byways, or build a route using our day trip picks below.

What to do if you’re a ….

Nature lover

The view from Mount Greylock, looking east.
Bob Shaffer
/
WBUR
The view from Mount Greylock, looking east.

Climb the highest heights: At 3,491 feet, Mount Greylockis the tallest peak in Massachusetts. It’s on the Appalachian Trail, but if you don’t feel like hiking, you can drive to the summit (during warmer months) where you’ll find Bascom Lodge and the War Memorial Tower. Unlike most ranges, which run from north to south, the expansive seven-mile mountain ridge of the Mount Holyoke range runs east-west. One option, head to the summit of Mount Holyoke (there are several named summits) and look for the Connecticut River’s oxbow in Northampton. You'll be putting eyes on a view that inspired a 19th century work of art worthy of the Metropolitan Museum of Art in New York.

Across the river is Mount Tom in Holyoke, a great hike to spot hawks making lazy circles in the sky. Its peak is famous among paragliders for having some of the best flying conditions in the world. In Great Barrington, Monument Mountain has several trails, with a 1,642 foot summit. Among the ways to the top, you'll find Mohican Monument and Indian Monument trails, which were recently renamed, by request of the Stockbridge-Munsee Band of Mohicans. Whatever path you take, at the highest point, you’ll have a stellar view of the Housatonic River Valley below.

Green spaces and water finds: Take a stroll along the region’s many accessible trails and wildlife sanctuaries. Among them, Arcadia in Easthampton is fabulous for birdwatching. In nearby Hadley, there’s an accessible boardwalk loop at the Fort River Trail, part of the Silvio O. Conte Wildlife Refuge. For an urban oasis of natural beauty, meander through Springfield’s Forest Park — and check out the Tuesday farmers market, which runs May through October. You should also see the beautiful Springfield Cemetery, hidden off Maple Street in the city’s South End.

There are many paths to walk in the expansive Forest Park in Springfield, Mass.
Elizabeth Román
/
NEPM
There are many paths to walk in the expansive Forest Park in Springfield, Mass.

  • For swimming, numerous freshwater lakes, including Upper Highland Lake within the Daughters of the American Revolution (DAR) Forest, are managed by the state Department of Conservation and Recreation, and a few by local towns. And there’s so much kayaking and paddling possible along the Connecticut River and its tributaries.

Explore on two wheels: Former train tracks turned into rail-trail routes connect several points around western Mass. The 9.5-mile Manhan Rail Trail runs from Southampton to Northampton. That connects bikers (or walkers and runners) to the Norwottuck Trail, which crosses the Connecticut River, heading 11 miles east, from the Damon Road parking lot in Northampton to Belchertown. Farther west, the Ashuwillticook Trail in Adams goes for almost 14 miles.

The glacial potholes in Shelburne Falls, Mass., along the Deerfield River in June 2024.
Raquel C. Zaldívar
/
New England News Collaborative
The glacial potholes in Shelburne Falls, Mass., along the Deerfield River in June 2024.

Geological wonders in the midst: The Trustees of Reservations oversee many natural areas in the state, including the Chesterfield Gorge, a rocky canyon cut-through by the Westfield River. Fantastical glacial potholes in Shelburne Falls are riverbed remnants of the glacial melt that created the Connecticut River Valley. In Holyoke, along Route 5, find yourself face-to-face with actual dinosaur footprints. In Turners Falls (one of the villages of Montague), Jurassic-era armored mudballs can be found at Unity Park, which is also near the site of a historic surprise attack and massacre in 1676 on a Native American encampment. While in Turners Falls, head to the Great Falls Discovery Center, the canal bike path and two unique stores: Loot, an industrial artifacts emporium, and Swanson’s Fabrics.

Shoppers get their pick of the industrial bric-a-brac available at Loot in Turners Falls, Mass.
Raquel C. Zaldívar
/
NENC
Shoppers get their pick of the industrial bric-a-brac available at Loot in Turners Falls, Mass.

Foodie

A meal to write home about: Up on a mountaintop, The Dream Away Lodgein Becket is a Berkshire legend — Was it once a brothel? In the 1970s, did Bob Dylan really stop in? — where you can dine in a 200-year-old farmhouse with an incredible garden. In Springfield, Liberty’s is known for its Mediterranean meat grinders and the chicken maqluba is a favorite. Nearby, find some good eats from India at Panjabi Tadka on Main Street. For tea drinkers and crepe eaters, sweet or savory, Crepes Tea House in West Springfield is the spot. Also in “West Side,” bNapoli is the place for a true Italian meal or an aperitivo. In Holyoke, check out two institutions: Nick’s Nest for dogs and ice cream, and El Rincón Boricua for a taste of Puerto Rico; there's a variety of mofongo and also camarones en salsa de ajo and carne frita. Head north for a more intimate meal in Sunderland’s 1867 town hall at the upscale Blue Heron. Dishes are curated with locally sourced ingredients. That’s a bonus for many restaurants in the region. Find them in this guide from CISA, a booster organization for local farms. (Just saying, never, ever pass up the opportunity to stop at a farm stand for local asparagus or in-season strawberries.) With the area’s sizable Polish population, if you’re hankering for golumpki, a bowl of flaczki or pierogi, you’ll find several delis and restaurants. Maybe stop in at Millie’s or Bernat’s Deli, both in Chicopee, or Janik's in Westfield.

A chocolate and vanilla twist from Creamy Delights' New York Style Soft Serve on a recent summer night in Hadley, Mass.
Jill Kaufman
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NEPM
A chocolate and vanilla twist from Creamy Delights' New York Style Soft Serve on a recent summer night in Hadley, Mass.

On the cold, sweet side: Among the many local ice cream makers, seek out Batch in Longmeadow and Mt. Tom’s Homemade Ice Cream and Candy Store in Easthampton. Some creamy heaven can be found at Creamy Delights' New York Style Soft Serve in Hadley, on Lawrence Plain Road. At Flayvors, also in Hadley (ice cream parlor hopping, anyone?), you can watch the cows chew their cud while you devour the scoops and sundaes they made possible. Farther west, in addition to serving Madagascar vanilla and dirty chocolate, SoCo Creamery in Great Barrington is the only shop we know of with a set of “Shakespeare" ice cream flavors, a nod to the theater group Shakespeare and Co., a couple of towns away in Lenox. (Try marzipan date orange zest, yum!)

Donut Dip doughnuts in West Springfield, Mass. in June 2024.
Raquel C. Zaldívar
/
New England News Collaborative
Donut Dip doughnuts in West Springfield, Mass. in June 2024. 

Bring on the baked goods: Western Mass. has incredible bakeries, like Hungry Ghost Bread in Northampton. They offer buttery scones and aromatic pies, but the jewel in the crown is really the variety of bread baked daily in a wood-fire stove. Generations of Puerto Ricans have made Springfield and Holyoke home, with standout bread and dessert makers at the Puerto Rico Bakery II on Armory Street in Springfield and, in Holyoke, Old San Juan Bakery on High Street. As for doughnuts, Donut Dip, around since 1957 in West Springfield, is still frying 30-plus varieties in-house, including maple bacon, red velvet, lemon-filled, old fashioned sour cream, twisted crullers and hot cross doughnuts for those observing Lent. Berkshire Mountain Bakery is known for its artisanal sourdough breads and its take-and-bake pizza. (The chocolate bread is also unforgettable.) The bakery is in the village of Housatonic, just a couple of miles from the Guthrie Center, founded by area resident and illegal dumper of garbage, Arlo Guthrie.

Brews and hard cider: The craft beer trail in western Mass. is long. In Easthampton, within walking distance of each other, New City Brewery and Abandoned Building sit behind a complex of partially renovated mills. Meanwhile, Fort Hill stands in the middle of a field where paragliders occasionally land. If you go to White Lion in Springfield at the right moment, you might spot former UMass star Marcus Camby or any number of NBA greats coming over from the nearby Basketball Hall of Fame. Bright Ideas is at MASS MoCA in North Adams (also in Westfield), where you’re welcome to pair your IPA with a cheese steak or falafel bites from Big Daddy’s Philly Steakhouse, just steps away.

  • A decade ago, Franklin County was the heart of hard cider country in western Mass., West County among its top cider markers. Now cider gardens (places to drink on premises, not just buy) are popping up on farms and orchards. Check out New Salem and Carr’s cideries.

The quiet type

A cozy corner inside the Montague Bookmill in Montague, Mass.
Courtesy
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Montague Bookmill
A cozy corner inside the Montague Bookmill in Montague, Mass.

Book enthusiast: “Books you don’t need in a place you can’t find.” That’s the motto of the Montague Bookmill, located in a winding, old building complex hanging over the Mill River, also home to other businesses like the adjacent Lady Killigrew Cafe. In Lenox, The Bookstore has been “serving the Community since last Tuesday,” but really for decades. Check out the recent documentary about its charismatic owner. Several wonderful new and used bookstores are keeping readers happy in Northampton and Amherst (e.g., Amherst Books, Broadside, The Raven, Booklink Books). In Springfield, check out Olive Tree Books on Hancock Street.

Historic homes: Centuries ago, several writers including Herman Melville lived or came to western Massachusetts to pen what became classics. You can take a tour of Arrowhead, Melville’s expansive home and garden where he wrote “Moby Dick,” and rent his studyto do a little writing of your own. The home and garden of celebrated poet and recluse Emily Dickinsonis in downtown Amherst. Pay tribute to her — and her desk — before heading to the cemetery where she’s buried. The aristocracy that Edith Wharton wrote about (and lived) can be experienced at her home, The Mount in Lenox. Also in the Berkshires, W. E. B. Du Bois’ childhood home in Great Barrington is part of the Upper Housatonic’s African American Trail. You can drive by Theodor Geisel’s home in Springfield, and then you and your kids can revel in his legacy at the Dr. Seuss Museum.

In Amherst, Mass., poet Emily Dickinson is buried within walking distance of her homestead on Main Street.
Lily Harris
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NEPM
In Amherst, Mass., poet Emily Dickinson is buried within walking distance of her homestead on Main Street.

Treasure hunt: Collectors of antiques who like to haggle alfresco over the price of 19th century furniture or paw through piles of vintage costume jewelry already know about the vast, outdoor Brimfield Flea Market. It's been running a week at a time for decades, during the months of May, July and September. If you head a little farther west along Route 20 to Palmer, several antique vendors are open year round — 200 of them at Yankee Flea Market.

Bridges to cross and one tunnel: Walk across the Connecticut River in Beaux Art style when you stroll along Memorial Bridgefrom downtown Springfield to West Springfield. In North Adams, Natural Bridge State Parkis home to the only natural white marble arch in North America, according to geologists. It’s made of 550 million-year-old bedrock marble, carved into its iconic arch by the forces of a glacial melt more than 13,000 years ago. Cross between South Hadley and Holyoke on the more recent Vietnam Veteran Memorial Bridge (a.k.a. Holyoke Bridge, South Hadley Falls Bridge and County Bridge), built in 1990. You’ll see the power of the Holyoke dam, some remarkable bird life and small crowds of people fishing (for sport, not dinner). If you time it right (May into June), detour over to the fish ladder to watch anadromous fish passing upstream through the lift. See if you can find the eastern entrance to the Hoosac Tunnel, a 19th century engineering marvel, built not without tragedy. It’s off Route 2, which, on a clear day, offers unbelievable views from the summit point in Florida.

The east entrance of the Hoosac Tunnel in Florida, Mass., in June 2024.
Raquel C. Zaldívar
/
New England News Collaborative
The east entrance of the Hoosac Tunnel in Florida, Mass., in June 2024.

Creatives

Theater-goers: A history of summer theater has been bringing actors and other city dwellers to the Berkshires for almost 100 years (and to the porch of the Red Lion Inn). Add to that several next-gen theater productions happening in Pittsfield, Lenox and other Berkshire towns. Check out stage offerings at many small theaters near Springfield and Amherst, and make sure to look up The Chester Theater, Double Edge and WAM.

Music, dance, film: In addition to the incredible offerings at Tanglewood, Jacob’s Pillowand MASS MoCA (including the Solid Sound festival, every other year), make sure to look up what’s happening at smaller clubs and halls. Check out The Foundry in West Stockbridge or the reopened Iron Horse in Northampton, Bombyx in nearby Florence and other Northampton areaspots. Greenfield has a slew of regular performances at Hawks & Reed, as does The Drake in Amherst. For jazz, it's Watermelon Wednesdays in West Whatley and Dewey’s Jazz Lounge in Springfield on Worthington Street, across from Theodore’s Blues, Booze and BBQ.

If Latin American music is the beat you dance to, Salsa and Bachata nightsare a regular thing at breweries, American Legion halls and in Northampton at the E.J. Gare Plaza, tucked between Herrell’s Ice Cream and Tellus & the Satellite Bar (more dancing in their “part-time nightclub”).

On a clear summer night, you can catch a movie outdoors at the Northfield Drive-In (which is technically over the border in New Hampshire, but we're claiming it anyway). Bad weather? Head inside to see curated indy, vintage and arts films at Amherst Cinema, Images Cinema in Williamstown and Pothole Pictures in Shelburne Falls’ Memorial Hall.

The Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams, Mass, in March 2024.
Jill Kaufman
/
NEPM
The Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams, Mass, in March 2024.

Visual art, museums, historical societies: The Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams is even more worth the trip when you take beautiful Route 2 and travel slowly around the hairpin turn before descending into town. The iconically American artwork of Norman Rockwell can be found at his museum in Stockbridge, and then head north on Route 7 to the Clark in Williamstown, known for its collection of French Impressionism and notable traveling exhibits.

In Holyoke, the International Volleyball Hall of Fame is a stone’s throw from the city’s Children’s Museum (there’s a carousel outside toward city hall). Nearby, in Indian Orchard, you can visit the Titanic Historical Society. Hidden in plain sight is Springfield’s recently renovated Pynchon Plaza — a tiny park of public art, with steps that take you between Chestnut and State Street.

Pynchon Plaza, view from overlook, facing the Springfield Museums in Springfield, Mass., in June 2024.
Donyel Le'Noir Felton
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NEPM
Pynchon Plaza, view from overlook, facing the Springfield Museums in Springfield, Mass., in June 2024.

In the Amherst area, a collection of 10 museums is part of the Five College Consortium (maybe you’ve heard of them? UMass Amherst, Smith, Amherst, Hampshire and Mount Holyoke colleges). Historic Deerfield is a preserved 18th-Century New England village that recently broadened how it tells its history to include more about the Pocumtuc tribe that lived in the area before settlers arrived. If you’re interested in fossils — beyond finding them on Route 5 in Holyoke — head to the Beneski Museum of Natural History at Amherst College (apparently the first-ever dinosaur trackswere found in the Connecticut River Valley). The Eric Carle Museum of Picture Book Art is adjacent to Hampshire College (and near Atkins Market — mmmm, cider doughnuts). A few minutes away on foot is the Yiddish Book Center. A place for more than a million of volumes of rescued Yiddish books, plus other historic artifacts like typewriters, the center also has a thorough exhibit on the history of Yiddish language and culture.

At the Yiddish Book Center in Amherst, Mass., typewriters used by writers of Yiddish literature are among the artifacts,  telling the story of a language now rarely used and of the people who spoke it.
Jill Kaufman
/
NEPM
At the Yiddish Book Center in Amherst, Mass., typewriters used by writers of Yiddish literature are among the artifacts, telling the story of a language now rarely used and of the people who spoke it.

A bit north and east, the Swift River Valley Museum in New Salem tells the story of four towns — Dana, Enfield, Greenwich and Prescott — that were taken by eminent domain in the 1930s to build the Quabbin Reservoir.

Jump to: Western Mass. | Central Mass. | Eastern Mass. | Cape Code and Islands


Central Massachusetts

You’re entering “the heart of the commonwealth,” the cutesy moniker given to Worcester — the state’s second-largest city — as a nod to its geographic centrality between Boston and Springfield. While Worcester may exceed or fall short of your expectations of its other tongue-and-cheek nickname, the “Paris of ’80s,” it’s a Gateway City that has historically invested in the arts, a thriving underground music scene and a litany of gorgeous public spaces. And in recent years, a focus on revitalizing its downtown has attracted restaurants, breweries, bakeries and stores — while bringing new patrons to some of its most beloved businesses.

Today, there are ample activities for any day-tripper to fall in love with the city and the many more communities that make up central Massachusetts.

For your planning purposes, the region includes all of Worcester County, and roughly — perhaps controversially — fewer than a dozen or so municipalities that sit in the northwestern shoulder of Middlesex County.

Spanning north to south ‘round the state’s middle like a wide ribbon, the region is polka-dotted with rural or urban sight-seeing options — plus parking that’s almost always cheaper than in Boston. If you’re trying to bop about the towns, traveling by car is quickest. However, two regional transit systems provide routes in and out of Worcester or Fitchburg/Leominster. If you don’t want any funny city business, the region lets you escape into the breathtaking wild, without forcing you to hike anything too hardcore.

If you’re more of a hip, Atlas Obscura adventurer, quick stops for quirk abound! Like this giant chair in “Chair City” Gardner, the city’s nod to its bygone era of furniture making. Perhaps you’d like to delight in examining a huge rock on Main Street in Fitchburg, whose preservation story is thick with irony. (It was apparently strategically exploded in order to exist forever.) Or, maybe you’d like to riffle through treasures — or rust-covered oddities — at a gruffer sort of vintage shop in Leicester.

Blue Collar Vintage Salvage in Leicester, Mass.
Jesse Costa
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WBUR
Blue Collar Vintage Salvage in Leicester, Mass.

Point is, there are many ways to keep your day trip poppin’, and we’ve tried to pick a few gems a little farther off the well-worn paths.

What to do if you’re a ….

Nature lover

Rock your world: Put on decent walking shoes and tread carefully down into the eye-popping geologic wonder of Purgatory Chasm, a state park down Route 146 in Sutton. Its attractions include both mysterious (and problematic) lore, but scientists think the imposing boulder-filled, quarter-mile chasm formed about 14,000 years ago. That’s when a super tall glacier is said to have suddenly spit out a surge of water, creating a ravine that today people — athletic or not — can play pretend parkour within. Most can navigate the rocks without issue — many a small child in Crocs have conquered them — but folks of all ages ought to avoid hubris, as injuries do happen. (PSA: In bad weather or even after a day of heavy rainfall, it’s best to skip out, as the rocks get dangerously slippery.) Once through its rocky center, you can also stroll along a few short and pleasant woodland trails. And back near the entrance, families often picnic. The park closes for winter and charges for parking from mid-May until late October ($5 for residents; $20 for non-residents).

  • If you super dig rocks but want a more modernity-meets-nature setting, head instead to Fitchburg. Intrepid hikers can summit Rollstone Hill to look out at the city and all the old pines that surround it. That is, if you’re not too preoccupied by the scene at your feet: Hunks of graffiti-covered granite from a defunct quarry.
Two people walk through Purgatory Chasm in Sutton, Mass., on a very hot day.
Jesse Costa
/
WBUR
Two people walk through Purgatory Chasm in Sutton, Mass., on a very hot day.

Do go chasing waterfalls: Spread across more than 150 acres, The Cascades in Worcester, Paxton and Holden offers a few somewhat challenging hikes that bring you past vernal pools in the springtime. Cascading Waters, as a prominent section is called, features a gentle waterfall that feeds into Cook’s Pond and greets you from Cataract Street in the city. (The waterfall sadly can fade into a trickle if you don't catch it in rainier weeks.) Some of the marked trails are quite steep, but adults and kids alike often manage and get to spy an abundance of native plants and mushrooms along the way. Keep in mind the waterfall looks most impressive after a decent rainfall.

  • If you’re interested in other waterfalls across the state, a project called New England Waterfalls lists and rates dozens of cascades here.
  • If you can’t get enough of nature, Hike Worcester, a project by the Greater Worcester Land Trust, offers this 2022 comprehensive guide, complete with useful trail maps and top-notch hikes around the city and its surrounding towns.

Peak outdoor power: In every season, nature lovers looking to maximize options for fun can find endless activities at these two enormous state-run parks: Wachusett Mountain State Reservation in Princeton and the Leominster State Forest. If you’re bold and fit, Wachusett maintains lovely trails to its summit. But those who want to view the valley below (or even sometimes Boston) from its 2,006-foot peak without sweating can drive up the mountain from around Memorial Day to mid-October. In the winter, many families enjoy cross-country skiing trails or hitting the slopes. Leominster State Forest draws folks looking to not only hike, but also fish, rock climb, mountain bike or swim. You can’t take a dip anywhere in the forest except for Crow Hill Pond, which has picnic areas and a skinny beachfront. However, you may fish and pull the boat into the waters at Paradise Pond. And while we can’t guarantee you’ll spot Bigfoot in these big ol’ woods, some folks really believe you just might.

Wachusett Mountain in June 2024.
Lisa Creamer
/
WBUR
Wachusett Mountain in June 2024.

Foodie

Dare to be hot doggin’: OK foodies, I know what you’re thinking. Hot dogs aren’t exactly Michelin star fare. But, our preferred split-top hot dog buns qualify as regional cuisine. Born out of practical need, you may be as surprised as this person (excuse the curse words, please) to learn the rest of the U.S. appears to risk their toppings with different buns. Of course, not all of these beloved central Mass. eateries keep their buns New England-style, but a hot dog tour is nevertheless in order as day trips demand a quick bite.

George's Coney Island hot dog restaurant in Worcester, Mass.
Jesse Costa
/
WBUR
George's Coney Island hot dog restaurant in Worcester, Mass.

  • First up are a couple local institutions that keep service no-frills and old-fashioned. As the Gardner News reports, locals love Lee’s Hot Dog Stand in Templeton (Baldwinville). The hot dog recipe has been unchanged for more than 50 years, and you should try one “with the works,” aka mustard, onions and relish. In Worcester, George’s Coney Island has been a family-owned fixture for more than 100 years. You can’t miss its iconic neon sign of a hand squeezing a hot dog with mustard spilling out. People flock to its wooden high-back benches — which locals have carved their names into — for soft-bunned tasty dogs, with many opting for the restaurant’s “signature chili” on top. “The works” here adds onions and mustard to the chili.
  • Hoping to eat a great hot dog in a more rural or roadside setting? Try Hot Dog Annie’s in Leicester or Murph’s Hot Dogs in Lancaster. Lines often stretch past the door of Annie’s little red shack, with most customers raving about Annie’s secret barbecue sauce, which workers describe as sweet and onion-y. And a great hot dog is one thing, but as WBUR previously reported, regulars at Murph’s roadside trailer also come for the fun of talking with the proprietor.
Wendy Harmon dresses a hot dog with onions and pickles at Hot Dog Annie’s in Leicester, Mass.
Jesse Costa
/
WBUR
Wendy Harmon dresses a hot dog with onions and pickles at Hot Dog Annie’s in Leicester, Mass.

Crack open some craft beers: There’s no shortage of craft beer spots in Worcester; here are just a few. It’s a hop-head paradise with Greater Good Imperial Brewing Company’s taproom and kitchen (many of the beers are a bold 8% or higher and the noshing menu is robust). If not everyone in your party is a drinker, Redemption Rock Brewing Company stacks its menu with beers and hard seltzers, and also mocktails, lemonades and a full coffee/espresso bar. Plus, well-behaved doggos are welcome inside, too. Finally, near the storied and now-updated Kelley Square rotary, Wachusett Brew Yard offers handcrafted ales and lagers you can sip while eating something delicious from the international food hall it sits beside.

  • Thriving for more than a decade now, the region’s arguably most famous beer haven is Tree House Brewing Company in Charlton. With several locations across Massachusetts, it’s maintained a cult-like following, in part over its hazy New England IPAs. Its Charlton taproom is its largest, with the company’s widest selection of craft beers and cold brew coffees, and plenty of seating outside and indoors. The owners recommend weekday visits if you hate long lines.
  • For anyone who wants a beer after traveling back in time at the living museum, Old Sturbridge Village, its picturesque host town has two breweries worth checking out. Rapscallion Pub invites you and your dog to its outdoor patio and offers lots of from-scratch vegetarian menu items. Meanwhile, Altruist Brewing Company has two riverfront beer gardens and is situated within a mill building that's more than 160 years old.

Diner car destination: Brunch options can make or break a community’s character. For central Mass., an embarrassment of classic diner rail cars has imbued the region with a small-town charm that suggests patrons might even like that the waitress delivers pet names alongside bottomless coffee. So, honey, how did we get so blessed with classic boxcar breakfast joints? According to the Worcester Telegram & Gazette, it’s because the city was once home to a major manufacturer of them: the Worcester Lunch Car Co. Today, several of its diners still operate in its namesake city, across New England and beyond. To experience the cars or similarly fashioned diners in Worcester, try Miss Worcester Diner (cash-only), Lou Roc's Diner (outdoor seats in nice weather), Marvin’s Corner Lunch (the tasty, cheese-covered Kelley Square special might require a post-breakfast nap), Ralph’s Rock Diner (an eatery and 21-plus event space for local live bands, trivia and comedy open mics) or Boulevard Diner (open nearly 24 hours on Thursday through Saturday). Blue Moon Diner in Gardner is another central Mass. Worcester Lunch Car Co. option to check out, as well as Charlie’s Diner in Spencer.

Gaming enthusiast

A stacked barcade: Looking for a lively and affordable spot to drink with friends while bouncing between nostalgic arcade machines and modern “rhythm” games? Freeplay Bar and Arcade in Worcester charges a flat rate ($7 on weekdays; $12 on Fridays and Saturdays) for full access to its near endless array of tabletop or traditional coin-op machines. This 21-plus spot that's open daily past midnight lets you stake out old-school staples like Tetris and Ms. Pac-Man, or get the blood flowing by bashing on pinball machines, hopping to the beat with DDR Extreme or challenging your pals on one its three air hockey tables. There’s an outdoor patio where you can cool off if the crowded room gets too warm or you need to decompress after failing to beat your own Galaga record.

A Gateway to Windows of gaming: If you love PC games or can’t log enough hours on the Nintendo Switch, but want to be a tad more social, head to All Systems Go Esports Facility in Worcester. The space boasts 40 “high-end” PCs (complete with fancy chairs) that offer a suite of pre-loaded games or internet access to your subscription-based gaming systems. It keeps four Switch consoles on deck so you and up to five of your pals can play pretty much every Mario game you can think of for $20 per hour. And in what feels like concessions built for serious gaming, the place lets you eat its pizza, wings or loaded fries at its computers (if you promise to be neat about it) and has an “Energy Bar” with specialty Red Bull-infused cocktails and non-alcoholic Red Bull tea drinks. For folks who want to get away from screens, the facility also lets you pick from more than 50 card or board games.

Escape from it all, if you can: Puzzle masters, rejoice! You can decipher hidden clues at The Gate Escape in Leominster (children ages 12-15 can play under adult supervision). If the love of your life really loves a good mystery, the staff will even let you hide a ring and propose inside. Playing with a larger party? Try Escape Games Worcester, which ideally fits about six to eight riddle-solvers in your private escape room (but might let you add a couple players if you ask nicely). The business allows walk-ins, but recommends you book in advance; kids 9 and older can play. It brags that its puzzles are challenging, claiming roughly a third of teams free themselves on time. Born from the mind of a former TV/film set decorator, Curious Escape Rooms in Fitchburg says its team puts serious effort into setting up unique puzzle rooms, adding it may be the only place that puts players inside a dollhouse.

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Eastern Massachusetts

Eastern Massachusetts is the densest part of New England by a lot of definitions: It's the most populous area, the most built-out, and has more things to do per-mile than most other regions in this guide.

A couple sits to look at the view of the Boston skyline atop Peters Hill, in the southern tip of the Arnold Arboretum in Roslindale.
Jesse Costa
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WBUR
A couple sits to look at the view of the Boston skyline atop Peters Hill, in the southern tip of the Arnold Arboretum in Roslindale.

There's so much happening here, locals more often refer to the smaller regions inside(ish) it. There are the North and South shores, which to an untrained eye look alike but to a Masshole are completely different planets. Along the New Hampshire border lies the Merrimack Valley, whose glory years as an industrial powerhouse have given way to revitalization around history and art. Out to sea are the Harbor Islands, tiny little jewels perfect for exploration and picnicking. And farther inland sits MetroWest, a hodgepodge of suburbia, corporate headquarters, thickets of woods and lots of trails to explore.

A man crosses a bustling Dorchester Avenue in Fields Corner at midday.
Jesse Costa
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WBUR
A man crosses a bustling Dorchester Avenue in Fields Corner at midday.

If you're coming from out of town, chances are you've thought a lot about what to see and do in Boston. And that's great; we offer some suggestions along those lines below. But don't sleep on Boston's vibrant, idiosyncratic and welcoming neighborhoods, where you can avoid throngs of tourists and instead try the food and music and cultures that gives this city its energy.

Since Boston is the hub (see what we did there?), highways and transit lines fire off in almost all directions (sorry, you can't take the T to the Harbor Islands). That makes for easy day-tripping, with or without a car.

What to do if you're a...

Nature lover

First let's go to the swamp. OK, it's a marsh: Nestled between East Boston and Revere is one of the area's best-kept secrets. Belle Isle Marsh is an urban wetland that provides excellent opportunities for trail walks and birding. It also lends itself to more day-tripping fun thanks to its proximity to the MBTA's Blue Line. Hop the line north for a reverie on Revere Beach, or head south to Eastie's Maverick Square and walk to Pier's Park to get a gorgeous view of the downtown skyline across the inner harbor.

Whose woods these are I think I know: If you're looking for a more woodsy adventure without alighting for New Hampshire's White Mountains, the Middlesex Fells offers great trails for walking and cyclists alike (even if they don't always like each other). Pack a picnic, try some kayaking, bring your fur baby for some good (permitted!) off-leash walking, among the other options available. Public transport is a little trickier here, but the Orange Line's Oak Grove stop is a 15- to 20-minute walk, and there are three bus routes. There's also parking at several locations along the 2,200-acre reservation.

Live deliberately and maybe catch a swim: Nestled on the edge of Concord, Walden Pond scratches a lot of rustic New England itches. There's the romance of Thoreau's effort to "live deliberately" along its waters, the beauty of the surrounding Adams Woods and Pine Hill, access to American history with the nearby battlefields for Lexington and Concord, and a unique art experience down the road at Lincoln's deCordova Sculpture Park and Museum.

Swimmers stand in front of the bathhouse at Walden Pond.
Robin Lubbock
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WBUR
Swimmers stand in front of the bathhouse at Walden Pond.

Bike to the sea: The Northern Strand Trail, connecting Somerville to Lynn (and then by surface streets to Nahant Beach), has been decades in the making and will take you through all sorts of scenery, from the casino glitz and industrial decay in Everett to the edges of the beautiful Rumney Marsh in Revere, to the leafy suburban streetscape in Saugus. It's a long haul but extending your ride to the Lynn (interim) commuter rail station can mean a transit-aided ride back.

Thar she blows: Bike trails, pond hikes, birding. Many of the above options take a little stamina to complete. But if you can't — or don't want — to sweat while enjoying nature, try a whale watching tour. With boats that leave both Boston and Gloucester, you have options for your departure. And depending on where the whales decided to while away their day, you could end up deep into Massachusetts Bay, sometimes within sight of Provincetown. This is also a great option during one of Boston's increasingly muggy heat waves, since the air over the water is significantly cooler. When you're out there, watch for some tell-tale signs while scanning the water: Look for plumes of mist coming from blowholes, sea birds sitting and diving in the middle of nowhere, and the occasional whale leaping into the air during a breach.

Historian

Pictured in the fall of 2020, one of the most popular attractions in Salem, Mass., is the Samantha Statue.
Jesse Costa
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WBUR file photo
Pictured in the fall of 2020, one of the most popular attractions in Salem, Mass., is the Samantha Statue.

It's not just witches: Most people pile into Salem in October for its sPoOoKy vibe, because the tides of time have eroded the harder edges of that awful period in witch-hunt history. But there's lots to do and see, both tourist-y and and more respectfully, about not just the trials but of the area's nautical heritage, literary bonafides and overall beauty. The downtown is served by the commuter rail and is a walk-and-shop pleasure, dotted with local artisans and noshes. Closer to Derby Wharf you can check out the House of the Seven Gables and enjoy a little olde-with-an-e time candy before hitting some of the more contemporary dining and drinking options.

Defend Boston! And then maybe have a snack: Georges Island in Boston Harbor is great for picnics and has a big honking fort to explore. Built in the 19th century, Fort Warren was a training ground for Union soldiers heading to battle during the Civil War. If you're from here, there's a very good chance you took a field trip to explore its now-abandoned battlements, and the dark passages inside, so if you're bringing the kiddies, maybe stick with the ranger tour. Outside the fort, unwind and unwrap your own sandwiches or make a trip to the snack cart.

A man, a plan, a canal: Lowell?: The name may scream Rhode Island to you, but the Pawtucket Canal Boat Tour is a great way to explore Lowell, perhaps the most emblematic former mill town in Massachusetts. Dug to take advantage of the Merrimack River during the Industrial Revolution, the city's canals now offer a great way to explore the textures of its textile history before disembarking and exploring the rejuvenated downtown.

The grist mill at Plimoth Plantation in 2015.
Jesse Costa
/
WBUR file photo
The grist mill at Plimoth Plantation in 2015.

The field trip favorite: For lots of adults in this region, a cherished memory was taking a field trip to the then-Plimoth Plantation. To move away from its Euro-centric view of the past, the museum has since spent years trying to incorporate more input from the Mashpee Wampanoag tribe to include the 10,000-plus years of history that came before the Pilgrims bumbled into this area. If you haven't been there since you were a kid, you can still see the colonial village, but there's much more to explore today with the Historic Patuxet Homesite. The site's name change in 2020 was intended to be reflective of this more representative — and accurate — historical account, though some Wampanoags say there's still more work to be done.

Family Trip Planner

Old time fun: Look, everyone loves Disney World and Six Flags, but sometimes you don't want your entire day to feel that extra. Sometimes, you want a place like Salem Willows, which combines a waterfront park with an arcade, bumper cars and boardwalk-style dining options like pizza, fried clams or ice cream. And despite fears that it would go away, Salem Lowe is still there offering its legendary — or infamous — chop suey sandwich.

Crates splash into the Fort Point Channel after children toss them overboard during a visit to the Boston Tea Party Museum.
Jesse Costa
/
WBUR
Crates splash into the Fort Point Channel after children toss them overboard during a visit to the Boston Tea Party Museum.

A block for kids: If you're in Boston with the kiddos, plan to hit this can't-miss doubleheader. Situated on either side of Fort Point channel, the Boston Children's Museum and Tea Party Museum is an easy and fun day out. The Children's is famous for its interactive exhibits, so be ready to play. And if your tykes need a little transgressive release, telling them they're allowed to throw crates of tea into Boston Harbor is too tempting to pass up.

Cool treats and fresh farm air: If you're looking for something a little more pastoral, you can't go wrong at some of the open farms in the area, like Kimball Farm in Westford. Grab an ice cream, hop on a hayride, take a trek on a pony, and grab a bat or golf club at the cages and ranges. Or, if you time it right, you can get some to-die-for fresh cider doughnuts in the fall.

A cookies and cream ice cream at Kimball Farm in Westford, Mass., on Wednesday, May 29, 2024.
Raquel C. Zaldívar
/
New England News Collaborative
A cookies and cream ice cream at Kimball Farm in Westford, Mass., on Wednesday, May 29, 2024.

Some low-hanging fruit: Apples aren't the only thing you can pick as part of a fun day out. Ward's Berry Farm in Sharon gives you a chance to harvest strawberries fresh from the bush. You can bag up a bushel of the berries (and yes we're calling them berries we don't have time for your internet-fueled pedantry). If you can’t get enough plucking edibles or florals from the dirt, Ward’s lets you run wild on its other varieties of fruits and vegetables, as well as its tulip and sunflower collections. You can also just go and enjoy a day of corn maze-running and hayride-riding.

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Cape Cod and Islands

New York has the Hamptons. New Jersey has the shore. And here in Massachusetts, we've got the Cape and Islands.

The Cape’s arm-shaped peninsula boasts 550 miles of unspoiled coastline, maritime character and seafood galore, making it a tourist hotspot every summer. In the 70 miles from the Cape Cod Canal to Provincetown’s Race Point beach, there are 15 towns, each dazzling visitors with their own unique beach town vibes. In the fall, the Cape quiets, offering a cozy and quintessential New England ambience, too.

Where exactly and when you visit these coastal havens depends on what you’re looking to do. But first, you must cross one of two bridges: the Sagamore to the north or the Bourne to the south. Deciding which to take depends on where you’re headed.

Boats are docked near the Chatham Pier Fish Market in Chatham, Mass., on Tuesday, June 11, 2024.
Raquel C. Zaldívar
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New England News Collaborative
Boats are docked near the Chatham Pier Fish Market in Chatham, Mass., on Tuesday, June 11, 2024.

Sandwich, the first exit off the Sagamore, offers a quieter coastal experience best known for its recently rebuilt boardwalk. A little farther down 6A, you’ll hit the summer tourist magnet Falmouth. Beyond its lively downtown, visitors are often attracted to its famous annual road race. Head to Chatham and you’ll find narrow streets, lots of seals, the Cape Cod Baseball League and high price tags on, well, everything. In Wellfleet, catch a flick on Route 6 at one of the country’s remaining drive-in movie theaters. Provincetown, despite being farthest down Cape, is one of the more convenient destinations to day trip from Boston because there’s a ferry. The area is a longtime LGBTQ+ and artist sanctuary that's increasingly known for its nightlife (we love a flawless drag show). Just be warned crowds balloon in P-town each year during Bear Week, Provincetown Carnival and Family Week.

A fisherman casts his fishing line out into the Cape Cod Canal in Sandwich, Mass.
Jesse Costa
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WBUR
A fisherman casts his fishing line out into the Cape Cod Canal in Sandwich, Mass.

To explore Martha’s Vineyard or Nantucket, take a ferry or perhaps find a friend with a big enough boat. Several passenger-only ferries will ship you to the Islands, like the Island Queen from Falmouth to Oak Bluffs on Martha’s Vineyard and the Freedom Cruise Line from Harwich Port to Nantucket. If you want your car, the Steamship Authority is your best bet for either island. However, car reservations must be made in advance, and wintertime slots often fill up. But if you’re willing to travel on non-peak days, hop on a waitlist; you may be in luck. Ditch the wheels and you can walk on the Steamship Authority’s boats without booking ahead.

If you're looking for bustle, Martha's Vineyard brims with activities for beach bums, foodies or families. Just a 45-minute ferry away, the island offers reliable public transit by bus that hits all its major points. Meanwhile, Nantucket's tinier landscape offers postcard picturesque scenes with fewer crowds but tamer recreational choices. Both places can boast about gorgeous beaches — and even presidents love the island vibes.

The Steamship Authority ferry dock at Vineyard Haven, Mass.
Robin Lubbock
/
WBUR
The Steamship Authority ferry dock at Vineyard Haven, Mass.

What to do if you're a...

Nature lover

Ride a bike: A great way to explore Cape Cod is by bicycle. The 25-mile-long Cape Cod Rail Trail is the region's best-known bike path. It winds between Yarmouth and Wellfleet, passing through Nickerson State Park, Cape Cod National Seashore and lots of little downtown areas. Another option is the Shining Sea Bikeway, which extends for 10.7 miles from Woods Hole to North Falmouth. (Pro tip: If you start in North Falmouth, you can jump off for a quick, summertime taco break at Quicks Hole Taqueria in Woods Hole.) For a straight-shot ride with constant water views, check out the Cape Cod Canal Bikeway. With entrances in Bourne or Sandwich, the two seven-mile paved trails run on either side of the canal. Though they're often slammed in the summer, bike rental stores are everywhere. (Some shops only allow week-long rentals, so check online and plan accordingly.)

A person rides a bike along the Cape Cod Canal Bikeway in Bourne, Mass., in June 2024.
Raquel C. Zaldívar
/
New England News Collaborative
A person rides a bike along the Cape Cod Canal Bikeway in Bourne, Mass., in June 2024.

Hit the beach: The Cape Cod National Seashore prides itself on over 40 miles of protected pristine beach, marshes, ponds and woods. It’s an outdoor-lovers' paradise. Check out the National Park Foundation’s guide to area beaches to learn more about where to go, seasonal fees, accessibility and even sharks. U.S. News and Travel also keeps a good list of popular Cape beaches (and the first choice, Mayflower Beach in Dennis, is a favorite for WBUR's assistant managing editor of newsletters, because during low tide you can walk for miles along tidal pools).

  • If you drive to the Cape, you can reimagine your beach day by off-roading. There is an off-road vehicle corridor at the Cape Cod National Seashore, but keep in mind that park rangers tend to be strict about fire and grilling rules. You can get the most of your off-roading beach day at Sandy Neck, a six-mile long barrier beach in Barnstable. Bring a grill, pack a cooler (of the non-alcoholic variety), set up a fire at night and even spend the night if you have a sticker and decide to make a weekend of it. The only downsides of Sandy Neck is the beach is rocky and you need to be aware of plover-related closures.

Remarkable creatures: Woods Hole, technically census-designated as part of Falmouth, is home to an Ivy League-level marine biology research center: The Woods Hole Oceanographic Institution. The private nonprofit is a pretty big deal — I mean, they helped find the Titanic — and you can get a peek into their work with their weekday tours (definitely book in advance).

  • If you'd rather look to the sky for feathered friends (or want an option closer to P-town), Wellfleet Bay Wildlife Sanctuary contains nearly 300 bird species within its five miles of trails. As you wander through a salt marsh, barrier beach, pine woodlands and a pond, bird watchers should be on the lookout for green herons, orchard orioles, eastern bluebirds and black-bellied plovers.

Foodie

Seafood for sale at the Chatham Pier Fish Market in Chatham, Mass.
Raquel C. Zaldívar
/
New England News Collaborative
Seafood for sale at the Chatham Pier Fish Market in Chatham, Mass. 

Fish of the sea: There are plenty of places to get your seafood fix down the Cape. (Seriously, it’s hard to choose.) But one award-winning spot for a cup of clam chowder is Skipper Chowder House in South Yarmouth. Restaurant-goers describe it as creamy and rich, and most importantly, packed with fresh clams. Sit on its deck overlooking the water and enjoy. You can hit up many other fried clam shack joints along the Cape where you can embrace the "belly or bust" clam-eating life. If you want to do a side-by-side comparison, there are two hotspots in Dennis: Captain Frosty's and Kream n' Cone. To break out of the Dennis shell, try Arnold's Lobster & Clam Bar in Eastham ('50s diner, "Happy Days" vibes), Mac's Chatham Fish & Lobster in Chatham (gluten-free options) and Seafood Sam's (it's got two fast-casual locations, one in Falmouth and one in Sandwich with some serious views overlooking the Cape Code canal).

A long line of tourists enters the Lobster Pot in Provincetown, Mass., in 2022.
Jesse Costa
/
WBUR
A long line of tourists enters the Lobster Pot in Provincetown, Mass., in 2022.

For lobster, it's a no-brainer to head to the Lobster Pot on Commercial Street in P-town. Since 1979, the iconic establishment has been slinging lobsters — pan-roasted, baked, stuffed, boiled and nestled in a toasted roll, lightly dressed in mayo, as our fishermen forefathers intended. Its neon sign draws locals and tourists alike. Save room after your seafood feast and walk along the crowded street to the legendary Provincetown Portuguese Bakery, which is over 100 years old, for sweet treats like pastéis de nata — a flaky, custard pastry that's simply dreamy. If you're just driving through the Cape to catch a ferry, a great pit stop is the Seafood Shanty in Buzzards Bay. The lobster rolls are so packed that some suggest splitting one between two people and asking for an extra toasted roll.

  • If you have access to a kitchen and want to cook for yourself, head to the Chatham Fish Pier Fish Market. Not only will you get to watch local fishermen unload their catch of the day, but you’ll have an ocean's worth of fresh seafood options. The market's take-out menu also offers the classics: fried whole belly clam and lobster rolls.
A lobster roll from the Chatham Pier Fish Market in Chatham, Mass., in June 2024.
Raquel C. Zaldívar
/
New England News Collaborative
A lobster roll from the Chatham Pier Fish Market in Chatham, Mass., in June 2024.

I scream, you scream, we all scream for … After a hot day at the beach, nothing beats ice cream for dessert. One of the most popular spots is Sundae School. Open since 1976, Sundae School now has two locations — Harwich and Dennisport — and a cult-like following for its small-batch flavors and high butterfat content. If you don’t believe us, the shop has been given accolades in numerous publications, including Boston.com, The Boston Globe, USA Today, Food & Wine and The Cape Cod Times. Other fan-favorites for a scoop — or three —include Twin Acres in Sandwich; Smitty's in East Falmouth, Mashpee and Barnstable; Cape Cod Creamery in Dennis, Hyannis and South Yarmouth; Four Seas in Centerville (which was recently listed for sale, but we hope stays just as good); and Ice Cream Cafe in Orleans. On Martha’s Vineyard, you can’t go wrong with Mad Martha’s, with shops in Edgartown, Oak Bluffs and Vineyard Haven.

Cranberries during the harvest process in Massachusetts.
Jesse Costa
/
WBUR
Cranberries during the harvest process in Massachusetts. 

Cranberries, everywhere: If you visit the Cape in the fall, you’ll be treated to a crimson feast for your eyes. One-fifth of the nation's commercial cranberry crop is grown in the Buzzards Bay region, according to the Buzzards Bay Coalition. Wade into the blazing red colors on a tour of one of the many local bogs. If you want a DIY-experience, take a walk along the Pamet Cranberry Bog Trail in Truro. It weaves between woods and sand dunes, and in the wooded part there’s a short loop to an old cranberry bog house that is pretty neat.

  • If you'd rather eat your berries than learn about them, head to Hearth N' Kettle in South Yarmouth and Hyannis (order the cranberry oatmeal pancakes, part of the Mayflower breakfast) or Somerset Creamery at any of its three locations — two of which are in Somerset and one in Cataumet — for a scoop of "cranberry bog" (dried cranberries, walnuts and dark chocolate mixed into a cranberry ice cream).

Historian

Lighthouses galore: There are 14 beacons across the Cape’s coast, many of which are historic and offer tours. Why so many? Well, before the Cape Cod Canal was built in 1914, ships sailing along the northeast had to go all the way around the tip of the Cape. The National Park Service, which operates the Cape Cod National Seashore, says during those early times there were more than 1,000 wrecks in the waters between just two of the Cape's outermost towns, Truro and Wellfleet. Within the National Seashore’s control, check out Highland Light, in North Truro, Nauset Light and Three Sisters (all in Eastham) and Chatham Light (which remains an active-duty U.S. Coast Guard station).

  • Let’s zoom in on those sinking ships for a second. During the mid-19th century maritime era, huts were built with driftwood from shipwrecks among the dunes in Provincetown and Truro in what’s now referred to as Provincelands (nearly 2,000 acres of protected sand dunes that’s now part of the National Seashore). Lifesaving “surfmen” would stock the shacks with food and water so if someone got shipwrecked, they’d have a safe place to ride out the storm. From the 1920s through the 1950s, the area transitioned to become more of a home for artists living in 19 historic shacks that still stand today. Some of their short-term residents include Eugene O'Neill, Jackson Pollock, Norman Mailer, Jack Kerouac and Tennessee Williams. However, in recent years, there's been tension on the Cape as the National Seashore has forced long-term shack residents and artists to leave.

Honoring native land: The Wampanoag Tribe of Gay Head (Aquinnah) on Martha’s Vineyard became a federally acknowledged tribe in 1987. Its tribal lands include Gay Head Cliffs, Herring Creek, Lobsterville and parts of Christiantown and Chappaquiddick. The tribe offers a recommended self-guided tour here, that takes you past cranberry bogs and the impressive Aquinnah Cliffs. Grab a snack at Alley's General Store in West Tisbury.

  • Speaking of Aquinnah, the historic Gay Head Lighthouse — which weighs 400 tons — was actually moved about 130 feet away from an eroding cliff.

Early settlers: Head to Provincetown to see the Pilgrim Monument, which was built between 1907 and 1910 to commemorate the first landfall of the Pilgrims in 1620. (It’s a way cooler historic landmark than Plymouth Rock, trust us.) The signing of the Mayflower Compact also happened in Provincetown Harbor. The museum that celebrates this history is charming and focuses on the region’s maritime history.

Out in the deep: Take a ferry to Martha’s Vineyard and check out the “Jaws” bridge. It’s located on Beach Road in Edgartown along Joseph Sylvia State Beach. And while doing this is illegal, for years people have jumped off the bridge into high tide. (We're not your mom or the police, but we'd regret not stressing that you should never attempt this in shallow waters.) “Jaws” takes place on the fictional island of Amity, and was filmed almost entirely on Martha’s Vineyard. Many locals were cast in the movie. In one famous scene, Police Chief Brody jumps over the bridge railing to save his kids. Even if you don’t swim, heading to the bridge is a fun way to experience Steven Spielberg’s iconic film in person. (You probably won't see a shark, but people do spot them along the Cape and Islands' beaches.)

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