Discover fall fun in the Berkshires during your stay at The Inn at Stockbridge

Fall Events and Festivals in the Berkshires

There is no place quite like the Berkshire Mountains in the fall. Between the beautiful fall foliage to see, the delicious seasonal eats to be devoured, and all the events and festivals in the Berkshires, it is no wonder why the area has been an American Fall destination for decades. Choose the Inn at Stockbridge as your perfect Berkshires bed and breakfast and you’ll be smack-dab in the middle of all the excitement.

Note: 2019 events are listed below. Due to the Covid pandemic, some Fall 2020 events have changed. Please visit each event for full updated info. The Berkshires are open, there’s plenty to see and do, and we look forward to welcoming you!

Fall Events & Festivals in the Berkshires

Annual Josh Billings Triathlon – September

Every year in September, the Berkshires host this exciting, unique triathlon event where outdoor enthusiasts team up in a relay-style endurance race and sprint to the finish line. The Josh Billings Triathlon puts teams to the test in events including bicycling, paddling, and running. Starting in Great Barrington, bikers travel 27 miles through 5 Berkshire towns to Stockbridge Bowl in Stockbridge. They then pass a wristband to paddlers that are awaiting their arrival in the Stockbridge Bowl lake. The paddling competitors can choose to paddle a canoe, kayak, or SUP board and set out 5 miles around the lake, meeting up with their running teammates at Camp Mah-Kee-Nac. Once the runners have the team wristband in hand, they sprint for 6 miles around the lake to the finish line at the Tanglewood Music Festival main gate in Lenox, where they are greeted and cheered on by tons of family, friends, and fans. This unique fall event is fun for all participants and spectators.

2019 Date & Time
Sunday, September 15, 9:30 AM
Distance from the Inn at Stockbridge
Starting line in Great Barrington, MA: 7.3 miles
Stockbridge Bowl in Stockbridge, MA: 6.5 miles
Camp Mah-Kee-Nac in Stockbridge, MA: 5.7 miles
Finish line at Tanglewood Main Gate in Lenox, MA: 5.7 miles

Annual Lenox Apple Squeeze – September

In September, Lenox becomes the best spot for Fall themed festivities as the annual Lenox Apple Squeeze kicks off the season. As a celebration of the apple harvest season and all things Fall, locals and visitors of all ages are welcomed to a street festival like no other. Enjoy local shops, restaurants, artisans, musicians, farm stands, and performers throughout the weekend. There will be seasonally inspired food and drinks available, including plenty of apple cider, hot, cold, or hard! Come out and relish the autumn beauty of the Berkshire Mountains for an event that is hailed “the best fall festival in the Berkshires”.

2019 Dates & Time
Saturday & Sunday, September 21 – 22, 10 AM – 5 PM daily
Distance from the Inn at Stockbridge
Lenox Chamber Visitor Center: 4.4 miles

Berkshire Botanical Garden Harvest Festival – October

One of the most iconic autumn events in the Berkshires, the Berkshire Botanical Gardens celebrates fall and the harvest just as fall foliage begins to peak in the region. Held over Columbus Day weekend, it is the perfect opportunity for visitors of the Berkshires to enjoy the entire 15-acre Garden campus during a uniquely beautiful time. Visitors have the opportunity to explore over 100 regional artisan vendors, a farmers’ market, plant sales, and educational offerings during the Harvest Festival. There is a fee to attend this event and all proceeds benefit the Garden’s horticulture and education programs. This wonderful event is the perfect opportunity for visitors to the region to view some of the breathtaking fall foliage and support local vendors, offering everything from food and drinks to handmade crafts. You won’t want to miss this one!

2019 Dates & Time
Saturday & Sunday, October 12-13, 10 AM – 5 PM daily
Distance from the Inn at Stockbridge
Berkshire Botanical Gardens, Stockbridge, MA: 3.7 miles

Paradise City Marlborough – November

Kick off the holiday season at Paradise City Marlborough, a dazzling exhibit and showcase of some of America’s most talented artists and master craft makers. Stroll around the show to view incredible sculptures and paintings, inspiring home furnishings, and spectacular jewelry and fashion items. You have the opportunity to purchase some of the most unique works of art available, which can be turned into wonderful gifts for family and friends that will leave them speechless. It is the perfect late fall destination for decorators, collectors, and homeowners with an appreciation for attention to detail.

2019 Dates & Times
Friday, November 22, 10 AM – 5 PM
Saturday, November 23, 10 AM – 6 PM
Sunday, November 24, 11 AM – 5 PM
Distance from the Inn at Stockbridge
Royal Plaza Trade Center in Marlborough, MA: 107 miles

Old Deerfield Holiday Sampler Craft Fair – November

Prepare for the holidays at this awe-inspiring craft fair in West Springfield, MA. Get a jump start on your holiday shopping and find one-of-a-kind pieces by over 240 crafters, designers, and artists. Visitors can expect to see jewelry, wood carvings, fashion, fine art, glass, specialty foods, and much more. Santa will be there for visits with children each day of the fair. And the crowned jewel of the event, the miniature village, will be on display for exploring. The display depicts the quintessential Berkshires village, telling a story and conveying the holiday traditions of Western Massachusetts. Kick off your Thanksgiving escape to the Berkshires with a visit to the Old Deerfield Holiday Sampler!

2019 Dates & Times
Saturday, November 16, 9 AM – 5 PM
Sunday, November 17, 10 AM – 4 PM
Distance from the Inn at Stockbridge
Better Living Center in West Springfield, MA: 47.5 miles

The Berkshires are a one-of-a-kind Fall destination. When you stay at the Inn at Stockbridge, you put yourself in the heart of all the fun Fall events and festivals that the Berkshires have to offer. The best part? After spending an exciting day exploring fall foliage and festivals, you have a wine and cheese reception to return to at our bed & breakfast where you can share your day with other guests! And if special events and festivals aren’t your style, there are many other exciting fall activities and attractions in the Berkshires to discover as well! Make the most of your fall getaway during your visit to us in the beautiful Berkshire Mountains at the season’s most colorful events!