New England Travel: 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 


  • 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.