What To Do In New England’s Berkshires

One hundred sixty-two years ago, Herman Melville made an impetuous decision to move to the Berkshires after going on a picnic with Nathaniel Hawthorne and Oliver Wendell Holmes. He was taken with the region’s beauty and believed it would be a quiet refuge that would be an ideal place to write.

Melville penned Moby Dick at Arrowhead, the farm he bought in Pittsfield, but the book was a commercial disaster and he wasn’t able to support his family from his writing and half-hearted attempts at farming. He left the Berkshires to become a customs inspector in New York after a 13-year stint at Arrowhead, but retained his strong affinity for the region.

The rural splendor that seduced Melville and others continues to bring creative types to the Berkshires from around the world, but the high cost of living means that it’s still difficult for starving-artist types to afford to stay for very long. There may be no other rural area in the country that has the combination of natural beauty and abundant cultural offerings as the Berkshires. The region’s proximity to New York and Boston makes it a popular, and pricey, weekend getaway.But you don’t have to break the bank to enjoy a short getaway in the Berkshires, especially if you visit during the week. On a recent trip to the region, we found a double room for $89 at the amiable Yankee Inn, just a few miles outside Lenox, a delightful town within spitting distance of a host of natural and cultural attractions. We liked it so much that we considered extending through the weekend, until we found out that our room rate would skyrocket to $259 per night.

Below you’ll find some suggestions for how to spend a short getaway in the Berkshires without breaking the bank. You can hit all of these places if you start in Williamstown, and proceed east and south to N. Adams, Adams, Hancock, Pittsfield, Lenox and Stockbridge.

WilliamstownHome to Williams College, one of the country’s finest liberal arts colleges, this handsome, walkable town has more going on than many cities with ten times its population. With the Williamstown Theater Festival, The Sterling & Francine Clark Art Institute and the Williams College Museum of Art in town, there’s always something going on in this classic New England town.

MASS MoCAThe Massachusetts Museum of Contemporary Art is one of the coolest museums I’ve ever been to, even though most of the exhibits went right over my head and reminded me of something that might have been discussed on an episode of Sprockets (see video). Three things I love about this place: 1) it’s located in a restored 19th century factory complex that’s an attraction in and of itself, 2) my kids loved the dinosaurs, Legos and opportunities to do arts and crafts projects in the museum’s Kidspace, and 3) the museum café is one of the best of its kind anywhere, with good food, drinks and ice cream at reasonable prices.

Bike the Ashuwillticook Rail TrailA scenic 11-mile bike/recreation path that begins next to the visitor’s center in Adams, and winds its way through Lanesborough and Cheshire. If you want to get your adrenalin flowing even faster, the region is also well known for its whitewater rafting.

Mt. Greylock State ReservationMt. Greylock’s peak is the highest point in Massachusetts and it’s a great spot for a scenic drive or hike. Melville is said to have loved the view of Greylock from the window of his home in Pittsfield.

Ioka Valley FarmMy boys, ages 2 and 4, loved the farm animals, slides, games and hayride at this family farm, which was established in the 1920s. It’s not dirt cheap at about $30 for a family of four, and I found their syrup for sale at a supermarket in Lenox for a lower price than they sell it for at the farm, but if you have young kids, you’ll want to bring them here for some low-tech, educational fun.

Melville’s ArrowheadThis is a great place to learn more about Melville’s fascinating life story and there’s a replica whale and whaleboat in the yard that makes for a great photo opp (see above).

Lenox- Classy little Lenox has a great, walkable little historic core that boasts some classic old New England homes, a great little bookstore, a host of expensive restaurants and the Old Heritage Tavern, a great place for dinner and drinks that’s a rare bargain in these parts. While in Lenox, you might also want to hear some live music at Tanglewood or take in a show at Shakespeare & Company.

Kennedy Park in LenoxRight next to Lenox’s lovely 18th Century Church on the Hill, you’ll find Kennedy Park, which is a beautiful, quiet place for hiking, jogging and mountain biking. There are 15 miles of shady, wooded trails – my favorite is the Red Neck – but all of them are quite pleasant.

Stockbridge– This is yet another enticing little town that’s perfect for a leisurely stroll. And if you like Norman Rockwell, who lived in the Berkshires for the last 25 years of his life, you’ll want to visit the Norman Rockwell Museum.

See How the Other Half Lived- The super rich have been summering in the Berkshires for a very long time, and there are a host of posh estates you can tour, or if you’re frugal or have a short attention span, gawk at from the outside. Check out Naumkeag in Stockbridge, and homes built for Edith Wharton (The Mount) and J.P. Morgan’s sister (Ventfort Hall) in Lenox.

See How the Other Half Lives- You might get kicked out, depending on how you’re dressed, but stop by the Wheatleigh in Lenox to see where those with some serious cash stay and eat when in the Berkshires. Room rates range from $715 for basic rooms to $21,000-$35,000 per night for use of one of their 19-room “palazzos.”

[Photos by Dave Seminara]