New England’s Best Small Towns


Because… sometimes the river trumps the sea.

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


New England’s Best Small Towns 


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

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


New England’s Best Small Towns 


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

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.)


New England’s Best Small Towns 


Because… this is what picture-perfect looks like.

The Dorset Inn, established in 1796. Photo by Jesse Burke

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


New England’s Best Small Towns 


Because… of this guy.

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


New England’s Best Small Towns 


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.


New England’s Best Small Towns 


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

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


New England’s Best Small Towns 


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


By Steve Almond

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.

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


New England’s Best Small Towns 


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

New England’s Best Small Towns


Because… you can go a little wild.


By Amy Sutherland

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.

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


New England’s Best Small Towns 


  • Dan

    Don’t miss Great Barrington Bra & Girl (GBBG) at the top of Railroad Street, the area’s only full-service bra shop, and one of the best intimate apparel and accessories shops that you’ll find anywhere!

  • lo

    also- see Brad at Allium-the best bartender in the Berkshires

  • Dan Shaw

    One of the best places to eat in GB is not on Restaurant Row–it’s Cafe Adam

  • Claudia

    If you are serious about food, this is the place. It’s a couple of miles north of town.

  • fred

    no one in Shelburne Falls drinks Bud… they (we) prefer locally made micro-brews

  • Marti

    Don’t miss Millerton NY, one of Arthur Frommer’s Budget Travel “10 Coolest Towns in America”. We are just 10 minutes or less to Sharon, CT and about 30 minutes to Great Barrington We’re a little bit Hip and a little bit Homey! To come on over.

  • Chris

    I have lived in Sharon all my life and it’s nice to see Sharon getting such recognition . The article got it right when it added Sharon.

  • Jonathan

    In Harvard, between orchards, you also have to go to the General Store (a gourmet/locavore paradise), get a cappuccino, sit on the Common, and look at the beautiful old houses. Then go to Fruitlands Museum.

  • Eve

    You forgot to mention the magnificent hillsides and valleys (ablaze with color right now) and the ancient pot holes and waterfalls, and my favorite – the very beautiful bridge of flowers.

  • Eve

    I forgot to mention above, I am talking about Shelburne Falls, MA.

  • J

    Couple comments:
    The bad: Putnam might be quaint because of the antiques, but other than that – it’s pretty much a dump. I grew up near there.
    The good: Hancock IS a beautiful town, not to mention the incredibly nice people. It’s also next door to another beautiful town, my other hometown of Harrisville.