Best of Massachusetts 2021 | The Outdoors Edition

Yankee editors pick the top Massachusetts attractions, dining, and lodging that highlight having fun in the New England outdoors.

By Yankee Editors

May 17 2021


Cape Cod’s Chatham Bars Inn is the best Massachusetts hotel on the beach.

Photo Credit : Christopher Churchill
TRAVEL NOTE:Before setting out to visit any of our Best of New England winners, please contact them or check online for updates on hours and operations this summer.
Cape Cod’s Chatham Bars Inn is the best Massachusetts hotel on the beach.
Photo Credit : Christopher Churchill

Best Massachusetts Outdoor Attractions

DOG EXCURSION Stodder’s Neck State Park, Hingham Is it a state park, or is it a dog park without the designation? Happily, it’s both. Dog owners up and down the South Shore know this 23-acre park as the place to bring their pets for social play. The “neck” is a peninsula at the mouth of the Back River, which means the land is bounded by water on three sides; the fourth side is guarded by a sturdy stone wall. Expect to find a mix of off-leash and leashed dogs here, many of which come to play practically every day. The landscape varies from grasslands and woods and hills, while the water offers ample opportunity for cooling off. THEATER Mendon Twin Drive-In, Mendon In the world of drive-in theaters, the c. 1954 Mendon Twin definitely runs with the cool crowd. You’ll not only enjoy a deftly curated collection of first-run and vintage movies but also primo concessions (triple cheeseburgers, mac ’n’ cheese bites, hot fudge sundaes) and access to a beer garden serving wine, sangria, and draft brews (past offerings have included local favorites Wormtown Brewery and High Limb Cider). Next to the beer garden’s 5,000-square-foot patio are fire pits where you can toast s’mores while keeping an eye on the big-screen action. mendondrivein.comFARM ANIMAL FUN Island Alpaca Company, Oak Bluffs White, beige, fawn, brown, rose gray, silver gray: The 50-plus Huacaya alpacas at this Martha’s Vineyard farm come in every color of the camelid rainbow. Bred to be prize winners and socialized to be gentle and friendly toward paddock visitors including kids, who are enchanted by alpacas’ soulful eyes and soft muzzles, these fiber-producing animals also keep the shop supplied with premium-quality yarns, textiles, and gifts. islandalpaca.comNATURE OUTING Walden Pond State Reservation, Concord An early proponent of social distancing, Henry David Thoreau lived alone in the woods for two years, two months, and two days, a mile from any neighbor in his rustic abode built near the shores of Walden Pond in Concord. While only a replica of the hut exists today, Walden Pond’s 200-plus acres of woodland make for a wonderful ramble, especially in the early morning hours, with the promise of a dip in the pond’s refreshing waters afterward. Note that the parking lot tends to fill up quickly on hot summer days. FLEA MARKET Todd Farm Flea Market, Rowley For nearly half a century, this seasonal North Shore attraction has been catering to treasure hunters in pursuit of antiques, collectibles, and original work by local artists and artisans. On any Sunday morning from April to November, bring some cash—you’ll save with free parking—and get busy browsing among the 200-plus vendors. The perfect piece to complete a collection, brighten up your decor, or spark a DIY project is just one discovery away. toddfarm.comOUTDOOR MUSEUM Old Sturbridge Village, Sturbridge New England’s largest outdoor living history museum makes the past anything but musty. If you haven’t visited since your schoolkid days (or ever), this 75th-anniversary year is a great time to experience the seasonal rituals of this 1830s farm and village. Engage with costumed historians, observe the care of heritage animal breeds, or perhaps even take a historical craft class and do your part to carry the past forward. osv.orgPUBLIC GOLF COURSE Crumpin-Fox Club, Bernardston Located just off I-91 in a small, rural Pioneer Valley town, Crumpin-Fox (named for a local 19th-century soda company) is not only one of Massachusetts’s most challenging courses but also one of its loveliest, thanks to its mix of woodlands and open rolling terrain. And after more than $1 million in renovations in the past few years, the sylvan setting remains timeless even as the golf carts now boast GPS. crumpinfox.coPYO FRUIT FARM Parlee Farms, Tyngsboro You’ll taste the difference but won’t necessarily see the science-guided, labor-intensive practices that the Parlee family employ on their 93 fruit-and-flower-planted acres. Go in June to pick strawberries and savor old-fashioned shortcake; time a July visit right, and you can pick both blueberries and fragile sweet cherries, which are easily collected from dwarf trees. Multitasking’s possible in late August, too, if peaches hold on while the earliest apples redden. parleefarms.comZIPLINE Catamount Zip Tour, South Egremont If you dangled in midair above the majestic Berkshires for only a moment, you’d be dazzled. Imagine the exhilaration of Catamount Mountain Resort’s two-hour zip trek, which begins with a summit chair-lift ride, warms you up with a 1,000-foot zoom along the Ridge Span, then sends you on the longest point-to-point zipline in the country: the 5,523-foot Catamonster. Views stretch forever (or at least to the Catskills).

Best Massachusetts Outdoor Dining

CITY PATIO DINING Oleana, Cambridge The patio seats at Oleana are so prized that you can’t specifically reserve them. You just have to cross your fingers. That’s because Ana Sortun’s team has created a verdant oasis near the tech epicenter of Kendall Square. Sheltered beneath umbrellas and basking in the glow of twinkle lights, you can tuck into Eastern Mediterranean favorites like tamarind beef and spinach falafel, and enjoy the signature baked Alaska for dessert. oleanarestaurant.comCRAFT BREWERY Exhibit A, Framingham There’s no doubt Trillium and Treehouse deserve the accolades for all the award-winning IPAs they produce in the Bay State, but we’ve got our eye on this small brewery in the industrial backlots of Framingham, a stone’s throw from the far bigger Jack’s Abby brewery. Local beer lovers have been snatching up such Exhibit A standouts as the Cat’s Meow, the lighter Just a Kitten, and the Kölsch-style Goody Two Shoes. Also be on the lookout for Wandering Thoughts, full of ripe citrus flavors. exhibit-a-brewing.comFARM STAND Verrill Farm, Concord If Verrill Farm’s name sounds familiar, it could be because you’ve seen it on a local menu. In operation since 1918, the farm supplies plenty of restaurant kitchens, but at the farm stand you can score the same ingredients for yourself, ranging from strawberries to squash to 30-plus varieties of heirloom tomatoes. Don’t feel like cooking? Verrill also has take-home meals and prepared foods, sandwiches, and a bakery that stocks the stand with homemade pastries and other sweet treats. verrillfarm.comICE CREAM STAND Richardson’s Ice Cream, Middleton To see a family farm at its best, stop at Richardson’s, where a family member has milked cows every day since 1695. To taste ice cream at its best, order a cone from the farm’s ice-cream stand. Richardson’s has been making super-premium ice cream (16 percent butterfat) for nearly 70 years, focusing on perfecting classics like vanilla and chocolate while expanding the flavor offerings to include grapenut custard, frozen pudding, peanut butter Oreo—more than 50 kinds in all. Bonus: After getting your licks in, you can check out the adjoining mini-golf courses, driving range, and batting cages. richardsonsicecream.comLOBSTER SHACK The Lobster Pool, Rockport Located in the northwest corner of Rockport, the Lobster Pool has the rare luck to face Ipswich Bay at just the right angle so you can watch the sun set over the water, with Plum Island in the distance. The nightly show is best enjoyed from a picnic table on the back lawn, accompanied by a steamed lobster dinner or lobster roll (the fried fish sandwich is also a winner). Don’t forget to BYOB—they’re happy to provide the ice. thelobsterpool.comMOUNTAIN-VIEW DINING Bascom Lodge, Adams This Arts and Crafts–style lodge sits at the summit of the state’s highest mountain, putting guests in the catbird seat for Berkshire sunsets. Open from late May until mid-October, the lodge offers both lodging and dining. The “food with altitude” features ingredients sourced from an extensive network of local growers and producers. Lunches are casual sandwiches and salads, but the evening offerings are more sophisticated than you’ll find at any other mountaintop lodge. And don’t miss the excellent breakfasts, or the on-site bakery. bascomlodge.netRIVER-VIEW DINING The Alvah Stone, Montague After browsing the broad selection of titles at the upstairs Montague Bookmill, it’s a treat to grab a table on the Alvah Stone’s patio, where you can sip a cocktail and watch the Sawmill River rush by. Bountiful salads with local ingredients and the restaurant’s famous cornbread with maple-bacon butter are just a few standouts from a menu that lures locals and tourists to this special spot. thealvahstone.comSEASIDE DINING Water Street Kitchen, Woods Hole Woods Hole is known as a place for departures and arrivals, the gateway to Martha’s Vineyard. But the food at Water Street Kitchen makes you want to linger awhile, spreading smoked bluefish pâté on crostini, dipping into a generous bowl of cioppino, or just watching the sunset with a cocktail in hand. Window seats are lovely, but sit at the bar for the best local gossip. WINERY Westport Rivers Winery, Westport With 80 acres under cultivation, Westport Rivers is among the largest vineyards in New England, and one of the oldest, too. The winery’s portfolio of crisp white wines—both sparkling and still—are rooted in its particular deftness with Chardonnay and Riesling grapes. They’re also the ideal accompaniment to local seafood. You can tour and taste every Saturday, or plan a visit around the annual sunset music nights (Fridays, beginning in mid-June) or hayrides (Saturdays in the fall).

Best Massachusetts Lodging: The Outdoors Edition

COASTAL CAMPGROUND Nickerson State Park, Brewster Smack-dab in the middle of Cape Cod, the 418 well-spaced camping sites at Nickerson State Park are in extremely high demand during the summer. If you’re one of the fortunate few to snag one, have fun swimming in one of the kettle ponds, exploring the hiking and biking trails that snake through the woods of pine and oak, and heading out on the 25-mile-long Cape Cod Rail Trail that skirts the park. STAY Starlight Llama Bed & Breakfast, Northampton Take your picnic breakfast, and choose your grazing spot. There are so many idyllic options on this conserved 120-acre plot enfolded by mountains, including a replica of Thoreau’s Walden cabin. The farm’s lineage reaches back six generations; the solar-powered, three-guestroom B&B is a glimpse of green energy’s future. You can feed the small llama herd, weed gardens, help with haying, or spend days hiking and biking and nights dark-sky gazing. starlightllama.comHOTEL ON THE BEACH Chatham Bars Inn, Chatham As a guest of Cape Cod’s most exclusive and complete resort, which first opened its doors in 1914, you’ll have the power to command your own little beach realm. Cabanas on the property’s quarter-mile private beach jut up like sand castles, and once you’re sequestered inside or supine on a lounger in the sun, you’ll have food and beverage service at your beck and call. North Beach Island, just offshore, protects your seawater bath from the wildness of the open ocean. chathambarsinn.comHOTEL PORCH Red Lion Inn, Stockbridge There isn’t always a pop-up performance or drink special on the front porch at this landmark hotel, which traces its origins to 1773, yet competition for rocking chairs is always fierce. Overlooking one of the Berkshires’ most vibrant crossroads, it’s a threshold that’s been crossed by countless luminaries. A few taps on your smartphone, and you won’t have to imagine Norman Rockwell painting this scene or James Taylor’s voice emanating from the landing. redlioninn.comISLAND INN The Wauwinet, Nantucket When National Geographic named Nantucket one of the 10 best islands in the world, few New Englanders were surprised. With its cobblestoned streets, deeply rooted maritime history, scenic lighthouses, and beautiful landscape, all framed by the Atlantic, the island has been a travel magnet for generations. And so has the Wauwinet, which has welcomed guests to its location at the edge of a wildlife sanctuary since the 1870s. Today a Relais & Châteaux property with 32 boutique guest rooms, four cottages, and a three-bedroom house rental, it boasts an understated elegance—along with a restaurant, Topper’s, that is touted as being just as unforgettable as its setting. wigwamwesternsummit.comLAKESIDE CAMPGROUND Tully Lake Campground, Royalston Run by the Trustees of Reservations, this tents-only campground on the shores of a serene central-Massachusetts lake sells out quickly each summer. Many campers bring their own kayaks to paddle to the sandy isles found on Tully Lake. Hiking trails lead to scenic Doane’s Falls, where Lawrence Brook tumbles over a series of ledges before it reaches the lake. PARK Normandy Farms Family Camping Resort, Foxboro When was the last time your RV stay came with concierge service? Sauna and Jacuzzi? Day kennels and dog-walking services? The offerings at the national-award-winning Normandy Farms—which indeed was built on farmland dating back to the mid-1700s—are as expansive as its 100-plus acres. Choose from nearly 400 sites, which range from basic to premium (water, septic, cable, high-amperage electric) and including a handful of cabins, yurts, pop-up trailers, and safari tents for the non-RV crowd. normandyfarms.comWILDERNESS LODGE Wigwam Western Summit, North Adams America’s Switzerland is yodeling its siren song again now that a long-abandoned Mohawk Trail landmark has visionary new owners. Wake up to rolling mountains and 800-plus acres of trail-laced forest when you stay in one of four comfy cabins or two main house units that share Florida Mountain’s summit with the renovated Wigwam gift shop, now a window-walled, lodge-vibe café famed for its cold-brew coffee and more than 20 homemade fudge flavors.

See More: Best of New England 2021 | The Outdoors Edition