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.

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

ADVERTISMENT

  • 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 http://tinyurl.com/nuqhc5

  • 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.
    1

  • 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.