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Looking for the perfect autumn escape? The Berkshires in western Massachusetts become a breathtaking wonderland every fall, with rolling hills painted fiery reds, golds, and oranges. Whether you’re a nature lover, an adventurer, or someone who enjoys cozy seasonal experiences, the region offers endless ways to enjoy the crisp air and colorful scenery. From apple picking to pumpkin festivals, these fall activities in the Berkshires promise unforgettable memories for visitors and locals alike.
Pick-Your-Own Apples at Hilltop Orchards
Located in Richmond, Hilltop Orchards is a must-visit destination for authentic fall fun. Visitors can wander through lush apple trees and pick their own crisp, juicy apples perfect for snacking or baking a warm apple pie. The orchard also features scenic walking trails, breathtaking mountain views, and a farm store stocked with local products like fresh cider, jams, and baked goods. Don’t miss a tasting session at Furnace Brook Winery, located on site, where you can sip apple wines and hard ciders made from the orchard’s harvest.
Hike to the Summit of Mount Greylock
Mount Greylock, Massachusetts’s highest peak, is a must for outdoor enthusiasts. As you hike to the summit, you’ll be rewarded with panoramic views that stretch across five states. Trails range from easy scenic walks to challenging climbs, making it accessible for every skill level. In the fall, the mountain transforms into a sea of vibrant foliage, making it one of the most photographed spots in New England. If hiking isn’t your thing, the Mount Greylock Scenic Byway offers a peaceful drive with breathtaking views and several overlook stops for photo ops and picnics.
Visit the Farm Stands at Windy Hill Farm
In Great Barrington, Windy Hill Farm is a local gem known for its charming garden center and seasonal farm stands. Visitors can browse freshly harvested produce, colorful mums, pumpkins, and homemade treats that celebrate the harvest season. The friendly staff and rustic countryside setting make it the ideal stop for those seeking a slower pace and an authentic fall atmosphere. Families will love exploring the orchard and enjoying the peaceful Berkshire countryside.
Step Into Literary History at The Mount
For a touch of culture amid your autumn adventures, visit The Mount, the historic home of Pulitzer Prize-winning author Edith Wharton. Set in Lenox, this stunning estate is surrounded by beautifully landscaped gardens and forest trails that come alive with fall colors. Visitors can tour the grand mansion, explore art exhibits, and stroll through the gardens glowing in amber hues. The Mount also hosts seasonal events and performances, adding a touch of sophistication to your fall activities in the Berkshires.
Experience the Naumkeag Pumpkin Show
No fall season is complete without some Halloween magic, and the Naumkeag Pumpkin Show in Stockbridge delivers just that. This annual event transforms the historic Naumkeag estate into a glowing spectacle of thousands of hand-carved pumpkins, whimsical light displays, and festive decorations. Wander through themed gardens, sip hot cider, and capture Instagram-worthy photos under a canopy of glowing pumpkins. It’s an enchanting experience for all ages and one of the most beloved fall traditions in the region.
A Season of Color and Charm
From scenic hikes and apple orchards to historic mansions and festive pumpkin trails, there’s no shortage of fall activities in the Berkshires to fill your season with color and warmth. Whether planning a weekend getaway or a day trip, each destination offers a unique way to experience autumn’s magic. And while you’re in the area, be sure to explore more things to do in Lenox, a charming town filled with art, culture, and cozy dining, perfect for a fall retreat.
