September in The Berkshires

September is a great time to visit The Berkshires! The air is cool and crisp, perfect for hiking and biking. The hordes of tourists and second-home owners have thinned, the leaves are changing, and there are plenty of reasons to visit the rolling hills of Berkshire County.

Hiking in the Berkshires

There’s no better time of year to enjoy the outdoors here – take a hike up Monument Mountain, or a scenic drive to the top of Mt. Greylock. Paddle down the Housatonic River on a serene canoe tour, or bike the historic Ashuwillticook Rail Trail. If you’re looking for even more adventure, check out the Aerial Ropes course at Ramblewild, the Mountain Adventure Park at Jiminy Peak, or take a rafting trip through the rapids of the Deerfield River with Zoar Outdoor. Summer might be over but the fun never stops!

Fresh Grass Festival at MASS MoCA

One of September’s major highlights is the Fresh Grass Festival at MASS MoCA. Fresh Grass has been a staple of The Berkshires music scene since 2010, bringing some of the best progressive bluegrass and roots artists to North Adams. This year the festival welcomes a star-studded lineup to the stage, including headliner Greensky Bluegrass, one of the hottest bands in the business right now. It’s a must see! And while you’re here make sure to check out the current installations at MASS MoCA – the largest contemporary art museum in North America!

Berkshires Theaters & Museums

There are plenty of other cultural attractions to see while you’re in town: The Colonial Theatre’s September lineup includes ballet, comedy, dance parties and more. Shakespeare and Company keeps the Bard’s work alive this fall, and Barrington Stage continues to offer world-class theater throughout the month. And don’t forget the wonderful, year-round offerings at The Norman Rockwell Museum!

Berkshire Fermentation Festival

The 5th annual Berkshire Fermentation Festival is day-long celebration of the diversity of all things fermented and crafted, with demos, lectures, a culture swap, science corner, book signings, raffle, live music, and more. Sunday September 22nd at Butternut Ski Resort.

Shantz Gallery

The Shantz Gallery’s exhibition of Chihuly glass sculptures continues until September 22nd. Dale Chihuly is one of the foremost contemporary sculptors, bringing the intricacies of glass blowing to life on a grand scale that will drop your jaw.

Lenox Apple Squeeze

The 40th annual Lenox Apple Squeeze is a long-standing tradition in Berkshire County, ushering in the Fall season. September 21st and 22nd.


Woofstock is Berkshire Humane Society’s annual fundraiser celebrating people and their pups! This year, on Sunday, September 8th, supporters are invited to run or walk to help raise funds for shelter animals.

Come see for yourself why September is a great time to visit The Berkshires! Contact The Red Lion Inn today to book your comfortable stay in Stockbridge, MA!