Fall Foliage Season in the Berkshires

Rolling hills in autumn on a cloudy but sunny day. As we say goodbye to the lazy days of summer, anticipation builds for what autumn will bring. Each new season offers its own unique adventures. But fall foliage season in the Berkshires is always something special. Sure, you might need to break out your sweaters and trade your flipflops for sneakers or boots. It’s a small price to pay in return for the spectacle that Mother Nature has in store for you when the days grow shorter and the nights turn cool and crisp.

The change starts slowly, with a hint of color here and there in early September. Then the brilliant hues of crimson and gold wash over the mountains in a wave. By October, the landscape is ablaze with vibrant shades of scarlet, ginger, and amber. It’s as if nature is screaming for you to get outside and drink in the lush beauty of autumn.

And that’s exactly what you should do. Pack your warmest woollies, your steadfast hiking boots and come to the Berkshires for a fall foliage getaway. By car or bike, on foot or on horseback, adventure awaits in the rolling hills of western Massachusetts. No matter if you’re a leaf peeping novice, or a seasoned foliage enthusiast, we’ve got some great ideas on how to embrace the sublime beauty of fall in the Berkshires.

By Car

You can cover a lot of ground when you get behind the wheel and take a leisurely scenic drive. Roll down the windows and breath in the earthy aroma of a crisp fall day and the riot of color painting the countryside. While there are literally dozens of roads to explore, we recommend you start right here in Sheffield following the Southern Berkshire Route. This 48-mile route winds through the southwest corner of the state, traveling through the villages of Great Barrington, South Egremont, and Ashley Falls with a slight detour to visit Bash Bish Falls.

By Foot

If you’ve brought your hiking boots, you’ll be hard-pressed to find a more beautiful area to explore than the Berkshires. Choose from among a challenging hike up a mountainside for a spectacular view, or strike out in search of waterfalls. One of our favorites is the Race Brook Falls trek in the Mt. Everett State Reservation. It’s challenging, but oh so pretty. But you can find trails from easy to moderate within an easy drive of our Inn.

By Bike

If pedaling is more your thing, by all means bring a bike or rent from a nearby outfitter. Mountain trails and country roads abound in the Berkshires. Whether you fancy a jaunt through farmland, a ride through towns and villages past historic sites, or a casual pedal along an old railroad track, you’ll find something to suit all abilities. Be sure to try our local routes as well, for an interesting tour of Sheffield.

By Horseback

Hop in the saddle for a horseback ride through a forest of gorgeous fall foliage. At Undermountain Farm in Lenox, you can wander through fields and pastures, and along miles of trails aboard a steady mount. Berkshire Horseback Adventures, also in Lenox, offers guided rides through Kennedy Park and along the trails of Lenox Mountain. If there’s an equestrian in the group, this is by far a terrific way to enjoy fall foliage in the Berkshires.

These are but a few of the fabulous ways to soak in the magic of autumn and the glory of foliage season. A fall getaway to the Berkshires should be on everyone’s bucket list, and may become an annual event once you’ve experienced it. Book a room at the Staveleigh House Bed and Breakfast in historic Sheffield, MA, the southern gateway to the beautiful Berkshires, and let us introduce you to fall foliage season in the Berkshires. Take advantage of our Fall Foliage Weekday Special. Reserve two or more consecutive nights, Sunday through Thursday, September 27 through October 29 and receive a 25% discount off our regular rates.

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