Fall Festivals in the Berkshires this Year

The Berkshires host their fair share of festivals throughout the year. Dance, theater, arts, opera, and more each have their spot in the limelight at some point on the calendar. But when fall comes to the Berkshires, and a riot of color paints the landscape, every day becomes festive. Keep reading to learn more about fall festivals in the Berkshires this year.

A premier destination at any time of year, somehow the fall speaks loudest in the Berkshires. Awash in the bright autumnal hues of red, yellow, orange, and amber, towns and villages throughout the region bask in the glory of fall foliage. Warm days and cool nights ready the landscape for Mother Nature’s brilliant display come September and October.

With apple picking and cider sipping, we toast the change of seasons and welcome all the fun festivities that ease us gently through fall. Join us as we celebrate everything from ghosts and goblins to local legends. Fall is the best time to visit us at our historic bed and breakfast near Lenox, MA. Here’s what you can expect from a fall getaway to the Berkshires.

Housatonic Heritage Walks

September 4 – 6, 11 & 12, 18 & 19, 25 & 26 and Oct 2 & 3, 2021

Get out your hiking boots and join dozens of volunteer historians, naturalists, and environmentalists as they take you on a tour of the Housatonic River Valley. The Housatonic Heritage Walks are a great way to get out and explore the region while learning a bit about the diversity of nature that exists here. Choose from more than 70 options that will have you paddling the river, biking country roads, or getting a behind-the-scenes look at art venues throughout the region.

Lee Founders Weekend

September 17-19, 2021

Come out and sing happy birthday to this quaint town in the Berkshires. Celebrating 244 years young, Lee puts on a show for 3 days every September during the Lee Founders Weekend. It’s a weekend filled with traditions. Starting out with “Taste of Lee” on Friday night, Main Street becomes a world-class buffet of tempting treats prepared by local chefs. Saturday dawns bright with a 5K race followed by the annual parade. Then get into the swing of things with sidewalks sales, street vendors, music and more.

Lenox Apple Squeeze

September 25, 2021

It’s apples, apples, everywhere when the streets of Lenox come alive with vendors serving up apple pie, apple cake, apple muffins, apple sauce, apple cider, and cider donuts during the Lenox Apple Squeeze. It’s hometown fun that attracts thousands of visitors each year. But it’s not just apples that create the buzz in the Berkshires during this event. Hop on a wagon ride through town. Let street performers entertain you with magic tricks and more. Visit the craft tents to get a jump on your holiday shopping. Or just sit back and enjoy the music that fills the air at this festive event.

45th Annual Josh Billings RunAground Triathlon

September 19, 2021

Named for a local humorist, the Josh Billings RunAground Triathlon celebrates this hometown hero with a triathlon that begins with a 27-mile bike ride, followed by a 5-mile paddle, and a 6-mile run. This fun-for-the-whole family event embraces its namesake’s philosophy of “to finish is to win.” More than 500 teams compete for bragging rights as they traverse the region from Great Barrington to the Stockbridge Bowl.

Annual Harvest Festival, Berkshire Botanical Garden

October 9, 2021

Celebrated over the Columbus Day Weekend, the Annual Harvest Festival at the Berkshire Botanical Garden brings together local musicians and entertainers, along with artisan food vendors, gardening workshops, and a farmer’s market. Hay rides and pony rides, a ghostly haunted house, and special surprises throughout the day make this celebration a treat for the whole family.

Join the fun fall festivals in the Berkshires this year to welcome the change of seasons. We’re here, in the heart of it all, ready to welcome you and share all that makes a Berkshires getaway so special.