New England’s Best Small Towns

From mountains to shoreline, our region offers no end of burgs filled with postcard ingredients: gleaming church spires, warm old red brick, jewel-like town greens. The 15 best towns, though, have something extra—a certain flavor that offers not just great snapshots, but also a great escape.

Hanover NH

Because… ivory towers make for a storybook escape.

courtesy of the hanover inn

courtesy of the hanover inn

When you get to Hanover, you see students. If you get there on a Dartmouth College football weekend, you see a Friday-night bonfire, hordes of alums, and jam-packed bar stools. Look deeper. Talk to locals who live here simply because they like it, or to folks who have retired here simply because there’s no place like it.

Yes, it’s the quintessential college town, where youthful enthusiasm combines with tradition to create something ageless. But it’s also the cultural heart of the Upper Valley. Try breakfast at Lou’s, lunch at Molly’s, dinner in Murphy’s. See what’s on at the Hopkins Center. Watch the world go by from the porch of the Hanover Inn. By Sunday, you may understand why so many love Hanover, why some never leave, and why you are now yearning to go back. —William Martin

Weston resident William Martin has written several novels, including Cape Cod, Back Bay, and the new City of Dreams, due out in May.


Essex, CT

Because… sometimes the river trumps the sea.

Photo by Paul Rezzendes

Photo by Paul Rezzendes

Underrated and therefore blessedly uncrowded, Essex’s central village juts into the Connecticut River some eight miles north of Long Island Sound. There are no rip tides here—just lovely river views and a nautical culture underscored by artifacts like the world’s first combat submarine, tested in these very waters. Would-be mariners can book a schooner ride at the Connecticut River Museum, or opt for a more leisurely fall-foliage trip aboard the steamboat Becky Thatcher. Across the river in East Haddam, the 133-year-old Goodspeed Opera House produces classic musicals like 42nd Street and Camelot; for drama of a different kind, head to nearby Gillette Castle, a Gaudi-esque palace built by William Hooker Gillette (Broadway’s original Sherlock Holmes), which offers tours, walking trails, and unparalleled river views. The appropriate way to wind down in Essex is with a cup of grog in the taproom of the 1776 Griswold Inn, where, surrounded by weathered oak beams and antique boat models, you can sing along to the inn’s banjo band. —Matthew Reed Baker


Great Barrington, MA

Because… it’s home to the Berkshires’ own Restaurant Row.

Photo by Keller + Keller

Photo by Keller + Keller

It’s got a cheesemonger, an old-time general store, and a new-age co-op market within a four-street radius. Yet the real allure of Great Barrington is Railroad Street, a single block with enough culinary delights to fill a weekend visit from beginning to end.

Friday dinner: Far-flung entrées (Himalayan antelope loin, Australian lamb) and a tasty bar menu elevate Pearl’s above the average surf-and-turf shop [EDITOR’S NOTE: Pearl’s closed indefinitely after the October issue went to press].

Saturday breakfast: Locals hit Martin’s early—as in, 6 a.m.—for hefty omelets with a side of town gossip. Tourists take the second shift and scarf bagels piled with smoked salmon and cream cheese.

Saturday lunch: The Yo-Yo Ma roll (bigeye tuna, avocado, mango, multicolored roe) at sushi bar Bizen makes fighting for a seat—or spending $100 on lunch—an acceptable tradeoff.

Saturday dinner: Get your fill of local flavor at Allium, where chef Michael Pancheri rewrites the menu daily after making the rounds of area farms.

Sunday brunch: Line up at 11:30 a.m. at 20 Railroad Street for juicy Kobe, Angus, and bison burgers, and to people-watch out the wide, street-facing windows.

Sunday pre-drive snack: Busy “micro-creamery” SoCo scoops gelato, sorbet, and ice cream in flavors like snickerdoodle caramel crunch and peanut butter mudslide. —Sascha de Gersdorff