The Berkshires Blog

Fall Festival Celebrations

By Nancy Macy

You can start at one end or the other, or somewhere in between. A drive through any part of the Berkshires in autumn is spectacular. Hillsides and valleys are ablaze with red, orange, and golden-yellow foliage. The cool air is clean and crisp. Every turn in the road presents splendid views and opportunities for family fun and adventure.

Fall in the Berkshires is as beloved by locals as it is by the travelers who visit this time of year from all over the world. In fact, this is a season of festivals that celebrate the bounty of harvest time and the natural beauty we are so fortunate to in our collective backyard. From lively street fairs to organized treks to the summit of Mount Greylock, we gather together and revel in it. Kick off the season by enjoying one of the many Heritage Walks offered over 3 weekends starting on September 17th. This is a great free way to learn more about the region.

As the lush green landscape and lingering notes of summer concerts at Tanglewood become a lovely memory, the town of Lenox still bustles with activity in the fall. The annual Apple Squeeze on September 24 and 25 brings a festive mix of local music, food, wine, craft beers, handmade goods and all things apple (even pizza) to the streets of downtown from 10-5 each day. Bring the whole family and your appetite. This is, without question, the place to have dessert first. Consider starting with a tall slice of Mary’s Carrot Cake, an Apple Squeeze favorite that sells out early year after year.

On the same weekend, Hancock Shaker Village in Pittsfield celebrates the season with The Harvest of Quilts, which opens on September 23, and the Country Fair on Saturday the 24 and Sunday the 25 from 10am-5pm. Set in the scenic foothills of Mt. Greylock, this is a spirited event rooted in the agricultural history of the village. Under the tents and at the food truck rodeo, you will find live music and the best of the region’s growers and artisanal foods, with craft beers by Big Elm Brewery and wines from Balderdash Cellars. Kids will love the wagon rides, face painting, old-fashioned Shaker games and the chicken races (yes, it’s a real thing and there are prizes to be won!).

Get some yummy treats for the fall.

Another family favorite is the Berkshire Botanical Garden’s annual Harvest Festival. This year’s Festival marks their 82nd year! This cherished tradition is one of the largest and longest running events of its kind in the Berkshires. Enjoy a celebration of community, local crafters and artists, entertainment, artisan food and more Saturday, October 8 and Sunday, October 9.

The peak of foliage season in the Berkshires varies from year to year but is usually early to mid-October. This is when you want to be on top of a mountain to take in the glorious seasonal color at full impact. The best place to do that is Mt. Greylock, the highest peak in Massachusetts. Every Columbus Day weekend, the town of Adams, which sits at the base of the mountain, welcomes thousands of leaf peepers for its annual Ramblefest block party on Sunday and the Mt. Greylock Ramble hike to the summit on Monday, Columbus Day. This year’s event adds a half marathon and 8K road race, the perfect way to enjoy an autumn day.

Wherever you are in the Berkshires this fall, you will find fairs and festivals that feature the best of the Berkshire harvest and New England hospitality. Join the party, and don’t miss that view!


Nancy Macy is a freelance writer and editor based in the Berkshires.