Berkshires Fall Foliage Day Trips

Spring has sprung and summer has sunned: now it’s time for some Berkshires fall foliage fun! Come soak up the gorgeous colors of autumn with a leaf-peeping getaway to the Berkshires of western Massachusetts.

October is peak fall foliage time in the Berkshires, with trees turning amazing hues all month long. The season begins late September and typically peaks during mid-October – and what a peak!

If you’ve been here during the fall you already know how incredible it can be but if not, well, let’s just say that words do not suffice.

One of the best ways to see all the glorious autumn colors our region has to offer is with a drive through the countryside. Luckily for our guests, our Berkshires bed and breakfast, The Inn at Stockbridge, is surrounded by a variety of excellent leaf-peeping drives and day-trips.

Read on to discover a few favorites.

Route 7 from Sheffield to North Adams

The Massachusetts stretch of U.S. Route 7 is well known for its stunning fall foliage. The drive we suggest passes through Great Barrington, Stockbridge, Lenox, and Pittsfield on its way to North Adams.

Berkshires Fall Foliage reflections on a pond

This route takes you past neat farms on gentle, rolling hills and small New England towns clustered around white-steepled churches. All of it, this time of year, drenched in the warm oranges, tans, golds, and reds of autumn’s mutli-hued glory.

Attractions along the route are endless. Each town along the route offers unique and excellent museums, galleries, orchards, farm stands, antiquing, dining, and more. Make a day of it – because it would be just as easy to spend a week and still not see it all.

Jacob’s Ladder Scenic Byway

Jacob’s Ladder Scenic Byway winds through five towns to provide some of the region’s most scenic, Berkshires fall foliage. The Byway (aka the Jacob’s Ladder Trail) follows U.S. Route 20 from Lee, MA, through Becket, Chester, and Huntington, to end in Russell, MA.

The 35-mile stretch takes you past beautiful woodland groves, dramatic cliffs, and endless vistas of stunning fall scenery. You’ll also drive by a number of area attractions that you may want to consider adding to your itinerary. The Appalachian Trail, the Becket Land Trust Quarry, Chester-Blandford State Forest, October Mountain State Forest, Keystone Arch Bridges, Jacob’s Pillow, and so much more.

Mount Greylock Scenic Byway

Berkshires Fall Foliage from Mount Greylock

Mount Greylock Scenic Byway is a bit farther away from our Berkshires inn but makes for an excellent day trip that is well worth your time.

The route leads from Lanesborough, MA to North Adams. As the name implies, this route will take you through Mount Greylock State Reservation, with a chance to see vast stretches of fall foliage from the breathtaking, 3,491 foot summit of Mount Greylock. Don’t miss it!

Other attractions include the Appalachian Trail, the Ashuwillticook Rail Trail, Mass MoCA, and Natural Bridge State Park, to name but a few.

A Berkshires Fall Foliage Getaway

Now is the time to plan your leaf-peeping vacation and The Inn at Stockbridge would be honored to serve as your Berkshires home away from home. Both the autumn colors and the guest rooms will only last so long, however, so don’t wait too long!