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.

| Boston Magazine |

Photo by Martin Child/Getty

Photo by Martin Child/Getty

Little Compton, RI · Hancock, NH · Sharon, CT · Woodstock, VT

Hanover, NH · Essex, CT · Great Barrington, MA

Camden, ME · Dorset, VT · Shulburne Falls, MA

Putname, CT · Lyndonville, VT · Harvard, MA · Rangeley, ME

Little Compton, RI

Because… it’s a little slice of Napa in New England.

Photo by Heather Burke

Photo by Heather Burke

Persnickety wine lovers thumb their noses at bottles poured east of the Sierras (or west of the Loire Valley). Pity they don’t know about Little Compton’s award-winning Sakonnet Vineyards, where, for $8, guests can taste the 50-acre spread’s finest wines. —Jamie Coelho

Cock of the Walk: Similar to a pinot grigio, it carries hints of apples and melons.

Vidal Blanc 2008: This white, fermented in stainless steel, has a sweet citrus taste and crisp acidity.

Rhode Island Red: The earthy finish is complemented by deep fruity flavor.

Reserve Chardonnay 2007: Aged a year in French oak, this varietal evokes honey and fresh-baked bread.

Gewürztraminer 2007: Floral notes and a dry finish make it an inspired pairing for spicy dishes.

Hancock, NH

Because… your great-great-grandparents might have slept here.

In the beginning, Hancock was a pit stop for the stagecoach crowd; today, it’s a favored destination for New England vacationers. Both sets of travelers have been warmly welcomed by the Hancock Inn, a bastion of Yankee hospitality since 1789. (B&B-phobes, take note: Centuries of operation haven’t precluded major renovations.)

Save for a general store, a café, and the inn’s dining room, the town itself has no shops or restaurants, a fact that history buffs applaud—along with the fact that every building on Main Street (where Paul Revere’s Bell #236 still rings on the hour) has earned a spot on the National Register of Historic Places. —Brittany Jasnoff


Sharon, CT

Because… it’s like a movie set (with actual movie stars)!

Photo by Keller + Keller

Photo by Keller + Keller

With no downtown to speak of, Sharonites must hit the post office to meet and greet their neighbors—but, oh, what neighbors. Campbell Scott, Michael J. Fox, and Kevin Bacon are among the homeowners in this Litchfield Hills enclave, population 3,000 (Meryl Streep lives a few towns over). Rigorous zoning has helped protect a cache of gorgeous old architecture—Federal, Gothic, Georgian—much of it along Main Street’s narrow town green. South on Main, you can ogle preserved estates amid sloping meadows, while rural Calkinstown Road has everything from 1870s farmhouses to chic modern abodes. You may not have the A-lister’s bankroll needed to swing a manse here, but, at least for a day, you can hang out and pretend. —J. L. Johnson


Woodstock, VT

Because… of this place.

courtesy of woodstock inn

courtesy of woodstock inn

Charm is deeply rooted in Woodstock, and reaches full flower in its namesake inn. Once a mansion owned by Laurance Rockefeller, the Woodstock Inn and Resort looms over the village center, yet not in a megahotel-swallows-rustic-hamlet kind of way. It entertains both locals and guests with live music, and the affiliated Billings Farm puts on festivals throughout the year. Inside, it’s newly luxe: The renovated rooms—deep loveseats, old-school plaids—come with giant TVs and regional art, and the Red Rooster restaurant has a Zen feel and upscale fare. Meanwhile, the seasonal activities (leaf-peeping in Quechee Gorge, toasting marshmallows at the inn’s outdoor fire pit) are utterly timeless. —Donna Garlough

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

Camden, ME

Because… this is the Main Street of all Main Streets.

Photo by Todd Dionne

Photo by Todd Dionne

With the Camden Hills as a backdrop and an oh-so-lovely harbor, this is small-town Maine so classic it might have come off a Hollywood backlot (Peyton Place was filmed here, in fact). The most iconic view is right through the historic heart of Camden, where every block has a story to tell. —Rachel Levitt

• The one-story building that now holds the Smiling Cow gift shop was rolled down Main Street from the village green in 1919.

• The town nearly burned to the ground in an 1892 fire, which started here.

• The spire of Chestnut Street Baptist Church, built in 1837, is a focal point of Main Street.

• Boynton-McKay Food Co. opened in 1893 and still features an art deco marble soda fountain counter rumored to have cost as much as a small farm.

• After the 1892 fire, this side of Main Street was rebuilt entirely of brick.

• The town held its first, and only, lobster festival here in 1947—with all-you-can-eat lobster for $1. (Too many littered shells saw the festival moved to nearby Rockland.)


Dorset, VT

Because… this is what picture-perfect looks like.

For restless city-dwellers, driving into Dorset is like entering a Thornton Wilder scene—the perfect example of what urbanites forfeit in favor of skyscrapers and dim sum. Lined with clapboard homes and divided by a town green, Church Street is home to the requisite general store (complete with ’70s-era gas pump) and several gracious inns where days are dominated by pancakes and porch-sitting. But the town is more than a relic: In addition to penny candy, its store has a gourmet deli and a separate wine room. Perhaps that’s why there’s no mass exodus here during mud season; even the summer people come up year-round. —Brigid Sweeney


Exeter, NH

Because… of this guy.

Photo by Todd Dionne

Photo by Todd Dionne

Home of the redoubtable Phillips Exeter Academy, this town has long prided itself on being an incubator of young overachievers. It’s fitting, then, that a 25-year-old wunderkind has taken the helm of its highest-profile restaurant. This summer Ben Hasty—former apprentice to French Laundry star Thomas Keller—signed on as executive chef at the Exeter Inn’s Epoch, launching an “upscale bistro” menu (think steak frites with onion confit and Worcestershire butter) that draws on local ingredients. And despite Exeter’s off-the-beaten-path location, Hasty is cooking to the standards of what he deems a very worldly crowd. “People travel here from all over the globe to put their kids into Exeter,” the Maine native says, “which gives Epoch extraordinary potential to be a destination restaurant.” (That is, as long as it can keep its chef: After tasting Hasty’s charcuterie plate, a brewery heiress from Montreal proposed kidnapping him to be her personal cook.) —J. L. Johnson


Shelburne Falls, MA

Because… if you can imagine it, they can make it.

There’s nary a Walmart in sight in this Deerfield River hamlet, which only stands to reason: Few places are more antichain than Shelburne Falls, where everything—and we mean everything—is handmade. Its streets hum with the energy of artisans making handblown glass bowls, quilts, kitchen knives, and much more. Fans of high-end crafts meander through the Shelburne Arts Co-op and individual studios, where laid-back locals tend to decompress with a can of Bud after a day of making beautiful things. Tempted to embark on your own treasure hunt? Here are a handful of gems to inspire you. —Matthew Reed Baker

Laurie Goddard: In her studio on Bridge Street, Goddard paints dreamy images inspired by the landscapes of Japan, Italy, and the Berkshires and filtered through an abstract expressionist lens.

Stillwater Porcelain: These ceramic artisans specialize in adapting Mother Nature’s own designs—including shells, flowers, and crab apple trees—for a variety of highly detailed pieces, from dinner plates to wall tiles to soap dishes.

Angelic Glass: After watching glassblowers shape delicate ornaments, you can buy their creations right next door at the Young & Constantin Gallery.

Molly Cantor: Featuring quirky depictions of birds, farm animals, and even Shelburne Falls itself, Cantor’s pottery and sculpture may come off as playful, but her method is seriously ingenious. After molding the form from a slab of basic clay, she coats it with a different-colored clay, then carves into the layers to achieve her trademark block-print look.

Ann Brauer: An NEA grant recipient with work at the Museum of Arts and Design, Brauer pieces together mesmerizing quilts and wall hangings that evoke New England’s seasons and landscape.

Putnam, CT

Because… a piece of history can be yours for the haggling.

Photo by Keller + Keller

Photo by Keller + Keller

Putnam’s pretty downtown hosts a wealth of shops, such as Vintage to Vogue (art deco furniture), Wonderland Comics (vintage X-Men!), and the 40-dealer-strong Jeremiah’s (dishes, dishes, dishes). All that pales, though, in comparison with the Antiques Marketplace. The largest antiques market in the state, it has 150 dealers and more than 50,000 items, including art prints, sets of sterling silver flatware, and the country’s premier collection of Stickley furniture. Haggling is de rigueur, and discounts are likely. Just ask owner Jerry Cohen: He recently unloaded a $5,000 oil painting for $3,500. The buyer then sold it at auction for 27 grand. —Francis Storrs


Lyndonville, VT

Because… your kids (and spouse) will thank you.

What New England town can be called “perfect” when you have a four-months-pregnant wife and a spirited 20-month-old in tow? Lyndonville can.

Cradled in the heart of Vermont’s Northeast Kingdom, it has foliage, hiking, and a sugarhouse that seemingly leapt, fully formed, from a Robert Frost poem. Most important, it has what I am ready to pronounce the greatest family resort on earth: the Wildflower Inn, where innkeepers Jim and Mary O’Reilly just get that it’s impossible to relax when you have to chase a kid around all day. What makes their inn so great? Let me count the ways.

1. On-site daycare by cheerful local college students.

2. A barn with actual farm animals that your daughter can pet—and then talk about for the next eight months.

3. A pool and a playroom full of toys to exhaust said child.

4. Food so sumptuous your wife will forget she was ever nauseated.

5. Nearby activities such as horseback riding and hayrides.

Of course, no New England town can be complete without a few eccentrics. We encountered ours on a hike, where a woman was dragging a large cross on wheels behind her. We assumed she was in community theater, but, as she eagerly explained, her purpose was indeed religious. And we took this for what it was: a sign that Lyndonville is God’s own country. —Steve Almond

Arlington resident Steve Almond is the author of Candyfreak and (Not That You Asked).


Harvard, MA

Because… the pickings are prime.

Tourists are relatively scarce in this burg of about 6,000. In fact, you won’t find a single motel or B&B. What you will find, though, are enough orchards to make Johnny Appleseed dance a jig.

Three of our favorites:

Carlson Orchards: This is the go-to for variety, with 21 kinds of u-pick apples on offer. The tour includes tips on how to pluck the best ones (e.g., the ripest are on the outer branches).

Doe Orchards: Great fruit, no fuss. As co-owner Larry Doe says, there’s “not a lot of hoopla” on this 60-acre farm, which boasts 12 apple types and 10 acres of cut-your-own Christmas trees.

Westward Orchards: Those hungry for something exotic can buy quince, along with pears and peaches, at the farm store, housed in a turn-of-the-century dairy barn. —Rachel Baker


Rangeley, ME

Because… you can go a little wild.

Photo by Walter Bibikow

Photo by Walter Bibikow

Traditional New England towns, with their trim black shutters and tidy village greens, can make me a little claustrophobic, what with all that historic perfection closing in. My antidote to the overdose of quaintness is Rangeley, a place that looks like what it is: an afterthought. Just a dozen or so wood-frame buildings strung along a lake, Rangeley was born to cater to 19th-century fishermen. Rusticators of all stripes have followed since, which is no easy task—there’s no rushing the 80 miles on two-lane Route 4.

Seasoned visitors know no one really goes to Rangeley for domestic niceties. They go for the endless lakes, the muscular mountains, the odd moose, and a wilderness so vast you get an itty-bitty feeling you thought only possible out west. Everything here is an outdoors binge, from hiking the Appalachian Trail up Saddleback Mountain’s 4,116 feet to panning gold in Coos Canyon. My preferred pastime, however, is to sit on my duff in a car barreling down Route 17. The scenic byway threads two monster lakes, Rangeley and Mooselookmeguntic, and has views grand enough to quiet two chatterboxes like my husband and me.

Eventually, we get hungry or tired or simply need to quit feeling so small, and we return to the town’s, er, finer points. Its restaurants, like the Red Onion, are no-nonsense: a simple deck and a bowl of hearty chili. The rooms at the old clapboard Rangeley Inn are equally spare, though comfortable and cheap. Only a few gift shops dot Main Street, nothing like the bonanza of gewgaws you find in Vermont. I love poking around River’s Edge Sports in Oquossoc, perusing the fishing flies and listening to locals regale clerks with their one-that-got-away stories. For this New Englander, that’s about as un-quaint as it gets. —Amy Sutherland

Charlestown resident Amy Sutherland is the author of What Shamu Taught Me About Life, Love, and Marriage.

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