Best of Massachusetts | 2018 Editors’ Choice Awards

Planning a Massachusetts vacation, day trip, or getaway? From dining and lodging to attractions that are well worth the drive, here are nearly 30 of our editors’ picks for the best of Massachusetts.

By Yankee Magazine

Apr 16 2018


2018 Best of Massachusetts | Chatham Pier Fish Market

Photo Credit : Chris Martino/Flickr
Planning a Massachusetts vacation, day trip, or getaway? From dining and lodging to attractions that are well worth the drive, here are nearly 30 of our editors’ picks for the best of Massachusetts.


Best of Massachusetts | 2018 Editors' Choice Awards
2018 Best of Massachusetts | The Mount
Photo Credit : John Seakwood

CINEMA OR DRIVE-IN: Mendon Twin Drive-inMendon

Since 1954, the Mendon Twin has been the summer go-to for under-the-stars movie-watching. While the vibe is nostalgic here, the movies are first-run and the projection is digital. The eats go beyond just bags of fresh popcorn to encompass burgers and pizza, and even ice cream sundaes for dessert. In the beer garden, you can sit by a fire pit with a draft beer or a glass of wine without missing a single big-screen moment. 508-473-4958

FAMILY ADVENTURE: Zoar Outdoor Family Float TripsCharlemont

Zoar Outdoor may be synonymous with whitewater thrills, but the company also runs Deerfield River rafting trips suitable for even the littlest paddlers, the 5- and 6-year-olds who are too young for introductory whitewater journeys. The Family Float Trips run midafternoon to early evening on a calm stretch of the river with one patch of mild rapids. Everyone is issued a paddle, helmet, and life vest, and the trip includes a stop at an island or riverbank beach for swimming and a picnic supper. 413-339-4010

FARMERS’ MARKET: Plymouth Farmers’ MarketPlymouth

Set on the grounds of Plimoth Plantation, this market gets extra points for its scenic backdrop and living-close-to-the-land vibe. Held outdoors every Thursday from May to October (and once a month indoors during winter), it rounds up the region’s bounty from 40 vendors that run the gamut from farmers and fishermen to beekeepers and bakers. Relatively speaking they’re a small group, but one clearly devoted to a larger mission—our Pilgrim forebears would no doubt have approved.

HISTORICAL EXPERIENCE: Hancock Shaker VillagePittsfield

For a religion focused on the next life, the Shakers sure had ingenious ways of dealing with this one. The radial stalls in the landmark round barn, for example, are an elegant display of labor-saving animal husbandry. The rhythms of their daily life echo in the demonstrations of woodworking and blacksmithing and visits to the medicinal herb garden. But nothing captures the Shaker spirit more than hearing voices rise in unison in Shaker tunes of worship. It wasn’t just a gift to be simple—these folks worked at it. 413-443-0188

HOUSE MUSEUM: The MountLenox

In building her home in the Berkshires, the wealthy and well-traveled novelist Edith Wharton created an English-style country estate with a French-style courtyard and an Italianate terrace. But the 1902 property is not as imposing as its pedigree; tours make the hostess seem present in every room. Summer and fall, Wharton spent mornings writing in her bedroom overlooking the gardens. In the dining room, she favored a round table so her guests could all engage in lively conversation. Talked out, they could end the evening with table tennis on the back terrace. 413-551-5111

MUSIC CLUB: The Guthrie CenterGreat Barrington

Located in the Old Trinity Church (c. 1829), where Alice of “Alice’s Restaurant” fame once lived, the Guthrie Center was founded by legendary singer-songwriter Arlo Guthrie as an interfaith church in 1991. Each summer, its weekly Troubadour Series draws top folk musicians to perform intimate concerts for invested audiences. Beer, wine, and a full dinner menu are available on show nights. 413-528-1955

NATURE EXPERIENCE: Cape Cod Field SchoolsSouth Wellfleet

Get up close and personal with the flora and fauna in one of New England’s most beautiful settings, the Cape Cod National Seashore and Wellfleet Bay Wildlife Sanctuary. In these excursions (basically environmental day camp for adults), you might study a stranded sunfish, photograph insects, or learn to identify scat and tracks. And come prepared: “We bill them as active, full-day, in-the-field programs, just so people aren’t caught off-guard by a five-mile hike or late-night—and cold—turtle patrols!” says Jenette Kerr of Mass Audubon. 508-349-2615

NEW CULTURAL ATTRACTION: The Amazing World of Dr. Seuss MuseumSpringfield

Fifteen years after the Springfield Museums complex honored native son Theodor Geisel with a huge sculpture grouping in the courtyard, Dr. Seuss got his own museum. Opened in June 2017, it delves into the creative impulses behind some of the world’s most beloved children’s books. In the brightly colored rooms of the museum’s first floor, interactive exhibits engage kids (and parents) in their own experimental doodles, rhymes, and storytelling. Memorabilia in the upstairs galleries hint at how Geisel’s talent blossomed in Springfield. 413-263-6800

SHORT HIKE: South Sugarloaf TrailSouth Deerfield

Not to be confused with its much bigger cousin in Maine, this Sugarloaf Mountain is, for nature lovers, a literal sweet spot. The 1.4-mile trail to the south summit is short yet steep enough to get the endorphins going; there are several trail branches and an auto road, which means hikers can change up their route up and back; and the 652-foot summit, crowned with an observation tower, is an unbeatable vantage point for gazing out over the Connecticut River, the Pelham Hills and Berkshire Hills, and the Pioneer Valley towns of Deerfield, Sunderland, and Amherst. 413-665-2928

SPECIALTY MUSEUM: New Bedford Whaling MuseumNew Bedford

Founded to preserve the history of the New Bedford whaling industry, this museum has grown into a cultural center, a destination for scholarly research, and a major repository of fascinating artifacts. Did we say major? Make that massive: The museum is home to the world’s most extensive collection of scrimshaw, the largest library of whaling logbooks, and the biggest model ship (not to mention four complete whale skeletons). This summer the museum unveils its latest conservation and digitalization project, a 1,275-foot-long panoramic painting of a whaling voyage. It’s believed to be—you guessed it—the longest painting in the world. 508-997-0046


Best of Massachusetts | 2018 Editors' Choice Awards
2018 Best of Massachusetts | Greydon House

BOUTIQUE HOTEL: Salt House InnProvincetown

Though the team behind Salt House Inn also owns the newer Eben House in Provincetown (plus two other properties in New York and New Jersey), we’re still stuck on this, the flagship of the Salt Hotels mini chain. Tucked away on a leafy side street and featuring clean lines, a soothing white-on-white palette, and thoughtfully collected antiques, it’s a handsome respite from the Commercial Street crush. On the lovely sun deck or in the shaded garden, you can tuck into daily breakfast treats such as a chorizo, spinach, and roasted red pepper frittata and homemade blueberry doughnuts. Like the luxe hand soap in the bathrooms? Pop over to the just-opened Salt Supply store to take some home with you. 508-487-1911

CAMPGROUND: Myles Standish State ForestCarver

About 400 campsites around four kettle ponds or in the woods are distributed through this extensive forest straddling the Plymouth–South Carver line. The location is convenient to Plymouth attractions, but there’s also plenty to keep you busy in the piney woods. Fifteen miles of bike paths encourage two-wheel exploration, and bridle trails entice equestrians. (Thirty-two campsites are reserved for horse camping.) Swim at your campsite pond or in the day-use area at College Pond. 508-866-2526

FAMILY LODGING: Wequassett Resort and Golf ClubHarwich

Imagine: You’re soaking in the rays as your kids paddle around this resort’s main pool overlooking the ocean when a 1950s-style Good Humor truck pulls up, doling out free ice cream for all. It’s this kind of amenity that makes the Wequassett so memorable for young guests. Other highlights for wee ones and their families include a free shuttle to a secluded Cape Cod National Seashore beach, a nautical-themed playground, and movie nights, but the pièce de résistance is the Children’s Center, offering programming for toddlers and kids such as scavenger hunts and a day shadowing the property’s pastry chef (perfect for budding foodies). 508-432-5400

HISTORIC INN: The Old Inn on the GreenNew Marlborough

It’s unlikely that the stagecoach passengers who bedded down in this 1760s Berkshires inn enjoyed quite the comforts as today’s guests, who sleep on bigger beds and perform ablutions in their private baths. But the restoration of the inn shows an unforced sense of history that makes a stay feel quite luxurious, even as the decor stays true to the inn’s colonial-era roots. Lest anything seem too modern, the dining rooms are lit entirely by candles and fireplaces. Five of the 11 rooms are TV-free. 413-229-7924

ISLAND LODGING: Greydon HouseNantucket

Uber-chic guest rooms and nautical-tinged decor by award-winning Manhattan design firm Roman and Williams. A cocktail list curated by star Boston barman Jackson Cannon. A laid-back fine dining restaurant (open year-round, by the way) helmed by Michelin-starred chef Marcus Gleadow-Ware. Amenities galore, including beach supplies on demand and bath and beauty products from the likes of Ursa Major and island favorite Follain. No wonder this inviting 16-room inn is set in what was once a doctor’s home practice: It’s a modern shot in the arm for Nantucket’s bed-and-breakfast scene. 508-228-2468

LUXURY ESCAPE: BlantyreLenox

A Berkshires country estate turned five-star hotel, Blantyre has seen its historic glamour polished to a high gloss under passionate new ownership (its principal buyer first fell in love with Blantyre on a visit 35 years ago). A multimillion-dollar renovation early this year refreshed the decor and expanded the spa; new dining options include a French bistro and, for high-end fare, a formal dining room called the Conservatory. One thing that won’t change: guests being pampered like Gilded Age grandees. 413-637-3556

NEW HOTEL: The Hotel SalemSalem

Set on the bustling Essex Street pedestrian mall, this chic 44-room boutique hotel occupies the building that once housed Salem’s downtown department store anchor. Innovative design includes some bargain-priced “microrooms” and more spacious rooms with sleeping lofts. Mad Men–era motifs such as the “tumbling dice” trompe l’oeil floor tiles and the gray herringbone grasscloth wall coverings inject a note of playfulness. Salem’s only rooftop bar is high enough to survey the city down to the harbor. 978-451-4950

ROMANTIC GETAWAY: The Inn at Castle HillIpswich

While it’s daunting to imagine living in the palatial Great House of the Crane Estate, the shingle-style former guesthouse has precisely the kind of seaside ease that suits a lodging on the green lawns above Crane Beach. Vistas from atop the knoll—marshes and beach and fairy woodlands—suggest command over all that you survey, but each of the 10 rooms is a hushed and private retreat made for two. The air of effortless privilege extends to on-site massage in six rooms. 978-412-2555

ROOMS WITH A VIEW: Beauport HotelGloucester

More than 150 years ago, Gloucesterman Fitz Henry Lane set up his easel at Fort Point to paint luminous canvases of Ten Pound Island and Gloucester Harbor. Today, the restaurant, bar, roof deck, and about half the rooms at the Beauport command those same views. The luxury hotel opened in June 2016 on the site of Clarence Birdseye’s first fish-freezing factory. It’s a perfect spot to watch vessels come and go in one of America’s most historic harbors. 978-282-0008 or 844-282-0008


This sprawling 1930s stone-and-timber lodge at the 3,491-foot summit of Mount Greylock is a welcome sight to through-hikers on the Appalachian Trail. Yet it’s also accessible by road for a getaway at the top of Massachusetts. Fieldstone fireplaces and arts-and-crafts-style seating give common areas a rustic panache, while private bedrooms and group bunk-bed rooms are more simply furnished. Breakfast and dinner are available. Some summer nights feature live entertainment, but the stars shine nightly. 413-743-1591


Best of Massachusetts | 2018 Editors' Choice Awards
2018 Best of Massachusetts | Chatham Pier Fish Market
Photo Credit : Chris Martino/Flickr

BREWPUB: The People’s PintGreenfield

While bottled versions of People’s Pint beers are available across Massachusetts, only the original brewpub restaurant serves them with the upper Pioneer Valley bonhomie that has made this 20-year veteran of downtown Greenfield one of its most enduring gastronomic institutions. Don’t expect extreme brews here: The well-balanced session ales, ambers, and stouts are brewed to be perfect for drinking with food or just laid-back sipping. Try the veggie peanut rice bowl with a pint of bright, slightly piney Training Wheels. 413-773-0333

BURGER: 20 Railroad Public HouseGreat Barrington

Dating back to at least 1919, the mirrored mahogany bar from the Commodore Hotel in Manhattan is one of the few things here that isn’t local. In a cozy space dominated by exposed brick, warm wood, and vintage-style lighting, chef Sean Corcoran serves produce and humanely raised meats from a long list of regional farms. The star of the show is the burger, which benefits from a custom grind of short rib and brisket; house-made applewood-smoked bacon is optional … and recommended. 413-528-9345

CAFE: SunbirdOrleans

Perched at the edge of a shopping plaza in Orleans, this café is a little slice of California cool on the Cape (think chalkboard menus, tables fashioned from wood slabs). Originally opened as the brick-and-mortar outpost of a popular but now-defunct Wellfleet food truck, Sunbird serves up porchetta-and-fried-egg sandwiches and quinoa porridge with coconut milk, dates, and candied ginger coupled with Counter Culture and Tandem coffee by day, and worldly snacks and plates—ramen, rigatoni with pork sugo, and pho, oh my!—by night. 508-237-0354

CHOWDER: Chatham Pier Fish MarketChatham

Hike down the steep slope of Barcliff Avenue, where this busy market dominates a busy working pier, and you might think our judgment has been swayed by the setting: the keening seagulls, the bobbing seals, the weatherworn fishing boats. But we’d choose this chowder even if it were spooned up miles from the coast. Rich with brine and clams, just creamy enough, never gummy, it’s worthy of a day’s journey from wherever you are. 508-945-3474

DOUGHNUTS: Back Door DonutsOak Bluffs

Everyone from The New York Times to Condé Nast Traveler has waxed poetic about these sweet treats, and for excellent reason: Fresh, cheap, and available between 7 p.m. and 12:58 a.m. in-season from the rear door of Martha’s Vineyard Gourmet Café & Bakery, these doughnuts might just be the island’s worst-kept secret (as demonstrated by the nightly long lines). Raised and cake varieties are on offer, and favorite flavors include maple-bacon and butternut crunch. Conflicted about deviating from your summer frozen-dessert routine? Order the “Charlie,” a doughnut of your choice topped with chocolate or vanilla ice cream and drizzled with chocolate. 508-693-3688


Designated simply by a hanging wrought-iron fish on Truro Center Road, this blacksmith shop turned restaurant has been reeling in lower Cape diners since 2007 with refined fare starring bounty from nearby purveyors: Nauset mussels, Longnook Meadows Farms lettuces, Wellfleet Chicken Coop eggs, and so on. In other words, chef Eric Jansen was doing farm-to-table well before it was buzzy. Not content to rest on their locavore laurels, however, Jansen and company now host a winter pop-up at his burger spot, Local 186, in Provincetown, and also operate the Crush Pad food truck at Truro Vineyards. 508-349-3399

HOT DOGS: Jack’s Hot Dog StandNorth Adams

Now starting on its second century in the same spot, this family-owned lunch counter is a downtown North Adams institution. You could order a burger, but the diminutive hot dogs custom-made by Wohrle’s in Pittsfield are Jack’s calling card. The two most popular variations are “with everything” (which translates as mustard, relish, and onion) and “chili cheese,” which signifies a dog wrapped in orange American cheese and slathered with the house chili sauce. All come served on squishy steamed buns. 413-664-9006

NEW BAKERY: The Baker New Bedford New Bedford

Opened in late 2016 next door to the police station, the Baker New Bedford may inspire some predictable joking about its clientele. But members of the local constabulary aren’t the only ones stopping in here for a cup of coffee and a doughnut—and a whole lot more. After honing his craft in Boston, Brandon Roderick chose his hometown of New Bedford for his Parisian-style bakery-café. It’s usually open until midafternoon, but fair warning: Roderick sells only what he baked fresh that day, so when the scrumptious breads, croissants, and quiches run out, time’s up. 774-202-1901

NEW ENGLAND CUISINE: Salem Cross InnWest Brookfield

Travelers whose appetite for the historic has been stoked at Brimfield or Old Sturbridge Village tend to make a beeline for the Salem Cross Inn, situated on a 600-acre farmstead that dates back to the early 1700s. The inn’s atmospheric restaurant and tavern elevate traditional dishes such as pot roast, clam chowder, and Indian pudding with an emphasis on from-scratch freshness and local ingredients—a laudable ethos that’s applied to more modern menu options, too, like vegan veggie ribbon noodles and cedar-plank salmon. 508-867-2345


Forgive our stretching the rules with this category. Vers (the word means “farm fresh” in Dutch) is technically a reopened restaurant, having shut down its original Chatham location in 2015. But its reopening in a larger space in Orleans, with an expanded menu and beverage program, has been the cause of too much rejoicing to ignore. Owners Jonathan and Karen Haffmans are back to doing what they do best: jewel-box plating, crystal-clear flavors, aha-moment flavor combinations. Don’t miss the tuna tartare, the pastas, or the “Truth or Dare” dessert, composed table-side. 774-561-2185

SEE MORE: Top 10 Massachusetts Summer Events of 2018Best of New England | 2018 Editors’ Choice Awards