Travel Guide: An Ideal Weekend Getaway in the Berkshires

The idyllic weekend retreat has some new treats this month.

Adventures in the trees at Ramblewild. / Photo by Ramblewild

It’s no secret the Berkshires are an ideal weekend getaway for Bostonians. But do you think you’ve done it all from Mount Greylock to Tanglewood? Think again. This autumn offers some new reasons to fall back in love with the region.

First things first: the great outdoors. Biking enthusiasts can hop on the newly extended Ashuwillticook Rail Trail, which now runs along an old train line from Pittsfield to North Adams, and take in 14 peaceful miles of forests, wetlands, and wildlife. For a more extreme diversion, head to the revamped Ramblewild, an aerial adventure park in Lanesborough where you can watch the fall foliage fly by on an exhilarating array of ziplines (for a truly unforgettable experience, book a new private guided climbing session).

If art and culture are more your speed, you’ve come to the right place. Mass MoCA in North Adams is showcasing some evocative exhibits this fall, including Amy Hauft’s “700,000:1, Terra + Luna + Sol.” The immersive, out-of-this-world installation features two enormous spheres, giving visitors the feeling of simultaneously being in the sky and on the ground. Another must-see is the Norman Rockwell Museum in Stockbridge, where, in addition to the artist’s greatest works, you’ll find 10 galleries with ever-changing exhibits.

The culture trip doesn’t stop there. On September 15, the region kicks off ArtWeek Berkshires, a 10-day festival featuring more than 100 events, from open studios and poetry readings to live musical performances. Also not to be missed are the Back Porch Music concerts under the stars at Hancock Shaker Village, where you can sit back, relax, and enjoy some live tunes with a picnic. Award-winning bluegrass musician Jake Blount takes his talents here on September 2.

If the mountain air has you feeling ravenous, there is no shortage of fresh dining options in the area. Hearty southern Italian fare (including lots and lots of fresh pasta) is on the menu at the new Amici in West Stockbridge, where you’ll find an expansive outdoor patio for warmer evenings. Or stop by Hot Plate Brewing Co. in Pittsfield, set to open in early fall, and raise a toast to crafting the perfect weekend getaway.

A peek inside the new Life House hotel in Lenox. / Photo courtesy of Life House

Getting There

Skip the traffic and hop aboard Amtrak’s daily service from Boston to Pittsfield. The scenic ride takes you to the heart of the Berkshires in just under four hours.

Staying There

Opened in 2022, Life House in Lenox is a reimagined writer’s mountain retreat with wood furnishings, ’70s-style upholstery, a library lounge, and a cocktail bar (typewriter not included). Another great option is the enchanting, recently renovated Apple Tree Inn in Lenox. The 1885 Victorian main house sits atop a hill and offers splendid views of the lush 22-acre property, which features two restaurants, live entertainment four nights a week, and a new mountain-view inground pool.