October 31st, 2023

Best Fall Hikes in the Berkshires

It’s that time of year: collections of pumpkins decorate doorsteps, apple desserts fill the shelves of local bakeries, and the air is infused with a crisp chill. Fall is here, which means so are some of our favorite activities—it’s time to take to the trails and enjoy the beauty of the season. We’ve compiled our top hiking trails in the Berkshires, so come along to experience it all for yourself. 

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Monument Mountain

In our opinion, hiking near Great Barrington is one of the best ways to spend a cool fall day. In the heart of the area—and steps away from the Briarcliff Motel—is Monument Mountain, a famous set of trails that are great for beginner and advanced hikers alike. If you’ve read William Cullen Bryant’s 1815 poem “Monument Mountain,” you’ll know that the hike up this peak is worth the trek. The 1,642-foot summit of Monument Mountain, referred to as Peeskawso Peak, serves up stunning views of the Housatonic River Valley that grows even more beautiful in September, October, and November. 

Appalachian Trail

The iconic Appalachian Trail runs almost 2,200 miles through 14 states, starting at Spring Mountain in Georgia and ending at Mount Katahdin in Maine. The scenic trail from Stockbridge to Great Barrington features exaggerated splashes of floating yellows, oranges, and reds, making it feel as though you’re walking through colorful confetti as you hike. 

October Mountain 

When it comes to fall hiking in the Berkshires, October Mountain tops our list. This state forest spans 16,500 acres—the largest in all of Massachusetts—and features trails for any hiker. Especially in the autumn, the views both along the way and at the peak will leave you inspired, just as they did American novelist and poet Herman Melville, who famously named this mountain as he viewed it from his home in the fall. 

Bear Mountain

At 2,316 feet, Bear Mountain is the tallest peak in Connecticut. Though the mountain features multiple ways to get to the top— each categorized as strenuous—we recommend opting for Lion’s Head. To do this, begin at this trailhead and follow the Appalachian Trail up Bear Mountain. This trail presents a show of fall leaves and more as it features lookout points along the way, a waterfall, and plenty of thick forests in various shades of red, yellow, and orange. Be sure to pack plenty of water—this trail is sure to make your heart start pumping. 

Olivia’s Overlook

In the heart of Berkshire County, you’ll find Olivia’s Overlook, a popular overlook and trailhead for six miles of rugged trails such as the 1.6-mile Charcoal Trail loop, the Brothers Trail, and the 3.2-mile Burbank Trail. These trails offer stunning views of Monument Mountain, Richmond, and West Stockbridge, especially in the autumn.

Kennedy Park

Along Pittsfield Road in Lenox, Massachusetts, you’ll find Kennedy Park, a town-owned and operated forest featuring old carriage roads and almost 15 miles of maintained trails. Though this park is picturesque during every season (think cross-country skiing and summer picnics), our favorite time to take to these trails is in the autumn. During this time, the golden sun peeks through the transitioning forest canopy as the leaves float down like confetti—the ideal recipe for a fall hike. The best part is this truly magical experience is yours to witness this season. 

Stay at the Briarcliff Motel

Hiking in the fall presents a sense of beauty and inspiration that is often lost. Whether you’re there to get a peek at the fall foliage or simply love being on the trails in any condition, you’ll need a place to rest and rejuvenate after a day well spent. Book your stay at our charming and pet-friendly motel in the Berkshires: the Briarcliff Motel. Don’t miss the natural beauty of the season—it’s time to hit the Great Barrington trails.