Fall Activities in the Berkshires

When it comes to fall activities in the Berkshires, we’re often voted one of the top places in America for fall foliage and for good reason. As summer fades and cooler temperatures take over, the mountains come alive with brilliant colors that just may leave you speechless. And we’ll let you in on a little local secret: October is peak fall foliage time in the Berkshires.

You may be asking yourself “So beyond leaf-peeping, what is there to do in the Berkshires during the fall?” Aside from the myriad of fall events to enjoy, visitors can expect to find some of the most fun fall activities and attractions in all of Massachusetts. Allow us to share with you some of our favorite ideas for fall activities in the Berkshires.

Best Fall Activities in the Berkshires

Visit Hancock Shaker Village

Plan a visit to the Hancock Shaker Village for a glimpse into the extraordinary lifestyle of the historical Shaker society of early American history. Open daily from 10:00 AM to 5:00 PM through October, this unique fall activity allows guests to take a tour of the village that resembles what the Shaker villages of the late 1700s and 1800s were like, including a large collection of artifacts and authentic architecture. There are events at the village and museum often, so be sure to check the Hancock Shaker Village website before your visit.

Paddle at Stockbridge Bowl

Experience the fall colors from a kayak or paddleboard at Stockbridge Bowl, our town’s publicly accessible lake. Though the water temperatures may be too cool for comfort when it comes to swimming in the fall months, the air is still suitable for an afternoon paddle. Launch your boat right from the shore and take in the view of the beautiful reds and oranges.

visit a Berkshires corn maze
Visit a local corn maze and “get lost”.

Make Your Own Beer & Cider Tour

Grab your favorite flannel, a cozy scarf, and some comfortable shoes and head out for a day of beer and cider tasting during your own custom-made brewery or cidery tour! There are a variety of breweries in the Berkshires, all serving some of the most unique craft beers you’ve ever tasted. And what would fall be without some cider? Hard cider that is! Visit any of the Berkshires cideries and get your fill of appl-icious beverages.

Get “Lost” in a Corn Maze

Looking for a Berkshires fall activity that challenges your mind and memory, and gives you hours of fun? Take a beautiful scenic drive over to Rolling Acres Farm in Southhampton, MA and get lost in their expertly designed corn maze. Open on weekends throughout September and October, Rolling Acres offers fun for all ages. Another great place for some fall fun is Ellsworth Hill Orchard & Berry Farm in Sharon, CT, about an hour drive from our Inn. Walkthrough their fun corn maze and do some apple or raspberry picking while you’re at it to enjoy on the ride back. Getting “lost” for a couple hours in a corn maze is one of the most “fall things” you can do!

Berkshires apple picking
Apple picking is the ultimate fall activity.

Go Apple Picking at Bartlett’s Orchard

Speaking of which, nothing says fun fall activity like “Pick-Your-Own” apple picking! At Bartlett’s Apple Orchard, guests can choose from a wide variety of apples to pick and take home with them. And if picking your own apples isn’t enough quintessential fall fun for you, they also have a year-round farmers market that serves delicious baked goods including apple muffins, turnovers, pies, cookies, and TA-DA cider donuts! Wash it all down with a freshly made cup of apple cider while sitting outside enjoying the beautiful fall scene.

Take a Thrilling Mountain Coaster Ride or Go Ziplining

If you’re an adventure-seeker looking for a new way do some leaf-peeping in the Berkshires, then check out Berkshire East Mountain Resort where you can take a thrilling zip-lining ride above the colorful trees or opt for the mountain coaster for a fast track down the mountain. Known for being a year-round outdoor adventure hub in the Berkshires, fall is an awesome to visit because of all the fall foliage to be seen from the heights of the zipline and mountain coaster!

enjoy an autumn hike in the Berkshires
Hear the leaves crunch beneath your feet as you enjoy an easy autumn hike.

Take a Scenic Drive or Hike

One of the wonderful things about a fall escape to the Berkshires is the simple act of driving around the mountain range and seeing all of the beautiful colors exploding from the trees. Better yet, strap on some boots and hit the trails. Hiking in the Berkshires is made that much more impressive when you’re surrounded by the colors and smells of autumn.

With so many fun fall activities in the Berkshires, you’ll need more than one day to do it all. Book a stay at The Inn at Stockbridge and enjoy easy access to all the leaf-peeping and apple-flavored things the area has to offer. Looking for a way to save? Call us about our Mid-Week stay discount and get ready for the best fall vacation you’ve ever had!