Find Stunning Waterfalls and Magical Gardens on a Berkshires Day Trip

You may not be rolling out the picnic blanket at Tanglewood this summer, but there are still plenty of reasons to head west on the Pike for the day. Among them: idyllic artist-inspired strolls, overflowing gardens, and one seriously hard-core mountain-bike ride.

Chesterwood / Photo by Kari Giordano/Courtesy of Chesterwood/National Trust for Historic Preservation

Approximate Drive Time From Boston: 2 hours and 20 minutes


Chesterwood, Stockbridge

The summer estate of legendary sculptor Daniel Chester French showcases his Colonial Revival house and studio, but it’s the hiking trails that’ll bring you back year after year. French was as talented a landscape architect as he was an artist, carving his Woodland Walk through the forest to take full advantage of the location, with carefully planned “vistas” to highlight points of beauty. Prefer a bracing climb to a vantage point with panoramas of the surrounding mountains? Try the Ledges Trail.

Pleasant Valley Wildlife Sanctuary, Lenox

Wend your way through wetlands, forest, meadows, and the slopes of Lenox Mountain, and you’ll likely encounter signs of this 1,000-acre sanctuary’s celebrity residents: an active beaver colony. Pathways range from family-friendly to strenuous; the All Persons Trail, meanwhile, provides universal accessibility, and the wildlife viewing deck overlooking Pike’s Pond features trail information in braille, large-print, audio, and tactile formats.

Stevens Glen, West Stockbridge/Richmond

At only 1.4 miles long, Stevens Glen is more of a pleasant walk than a vigorous hike, but the scenery makes it more than worthwhile. Formerly a loop but now an out-and-back trail due to erosion of creek beds, the path meanders through hemlock forest along what were once carriage roads, wide enough to allow for social distancing. The prize awaiting you at the end: a waterfall view and several lovely spots for contemplation.

Mount Greylock / Photo by Kirkikis/Getty Images


Ashuwillticook Rail Trail, Lanesborough to Adams

Hop onto this peaceful 12.7-mile paved path—an old rail route that traces the Hoosic River and the Cheshire Reservoir—for gorgeous water and mountain views, not to mention the occasional chicken or turtle sighting. While some maintenance has been planned for this season in the Lanesborough/Cheshire area, much of the trail remains wide open and ready to ride.

Great Barrington to Umpachene Falls, New Marlborough

Fire up the GPS and get ready to take a ride through some of the most unspoiled towns in the Berkshires, ending at a rolling waterfall that fairly screams out for an Instagram post. Start in Great Barrington and head south for about 12 miles, passing by the oldest covered bridge in the state and pedaling through picturesque farmland with lovely glimpses of the Housatonic River.

Mount Greylock Summit, Lanesborough to Adams

Careful on those hairpin turns, and be prepared for four seasons in a day: Called “the ultimate cycling destination in Massachusetts” by Bike New England, this 37-mile round-trip challenge begins with a quad-burning ride up Lanesborough’s Rockwell Road to ascend 3,941-foot Mount Greylock. The descent back down into North Adams gives any roller coaster a run for its money.


Did someone say tailgate? Long a local favorite for pre-Tanglewood drinks and dinner, Zinc Bistro & Bar in Lenox is offering its jambalaya, coq-au-vin, and famous burger for pickup.


Literally Stop and Smell the Roses

The Bridge of Flowers in Shelburne Falls is one of the most photo-worthy spots in the western part of the state. Once a trolley bridge, it’s been transformed into a magical garden of flowering plants, vines, and shrubs—like a fairy with a green thumb cast a spell over an old railroad trestle.


Got Cat in the Hat fans in your crew? Swing by Springfield’s Dr. Seuss National Memorial Sculpture Garden to spot your kiddos’ favorite characters—including the titular silly feline—cast in bronze. If you prefer gardens of the blooming variety, the historical Naumkeag Estate in Stockbridge delivers, with 48 acres of lush roses, beautifully sculpted evergreens, and more. For a much-deserved indulgence after a day’s exertion, stop by Charlton’s Tree House Brewing for contactless pickup of its coveted unfiltered IPAs and rich stouts.

More Day Trip Ideas to Escape the City This Summer