New England Travel: 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


  • 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.