4 of the Best Upcoming Fall Festivals in the Berkshires

Fall Festivals in the BerkshiresWith crisp air, vibrant foliage, and an abundance of things to do, there is no better place to be than the Berkshires during the fall season. Autumn also marks the beginning of fall festival season! These fun-filled events celebrate everything from town history to the bounty of the autumnal harvest. If you’re planning to come to the Lenox area during the season, you should check out one of these fall festivals in the Berkshires.

Discover more fall festivals in the Berkshires and other must-do’s when you request our free Vacation Guide! It’s also filled with great recommendations for local dining, shopping, entertainment, and more.

4 of the Most Fun Fall Festivals in the Berkshires

  1. Lee Founders Weekend (September)

This 3-day festival celebrates the anniversary of the town of Lee while providing plenty of fun for all ages.There is delicious food, art, music, a community block dance, crafts, magic shows, face painting, a duck derby, a vintage tennis tournament, sidewalk sales, street vendors, and much more. A hallmark of the festival is the Hometown Parade that features antique cars, the Lee High Band, The Berkshire Highlanders, Lee Fire & EMS, and fantastic floats! With so much to see and do, you’ll hardly be able to do it all in one day!

  1. Fall Foliage Festival (October)

Celebrate the “magic of the Berkshires” at the 62nd annual Fall Foliage Festival! Guests are encouraged to incorporate local folklore, such as witches, fairies, and wizards, into their costumes and festival experience. The main event of this autumn celebration is the Fall Foliage Parade, so be sure to grab a spot along the streets of Pittsfield for a festive procession you won’t soon forget!

  1. Lenox Apple Squeeze (September 23rd-24th)

The Lenox Apple Squeeze exalts the fall harvest with a variety of activities for the whole family!  You’ll be able to treat your taste buds to all sorts of delicious recipes featuring Lenox apples. It’s also a great time to get out and experience the autumn beauty of the Berkshires. The Lenox Apple Squeeze is an all-around fantastic way to celebrate the arrival of fall!

  1. Botanical Garden Harvest Festival (October)

This is one of the most popular fall festivals in the Berkshires and a favorite among the locals. More than 12,000 visitors attend to take advantage of the wide array of family-friendly fun including a petting zoo, horseback rides, live music, a haunted house, a farmers market, and more. You won’t want to miss it!

Need a Place to Stay For These Events? We’ve Got You Covered!

Fall Festivals in the BerkshiresWhile attending all the best fall festivals in the Berkshires, be sure to book your stay at the Gateways Inn! With rooms that combine timeless style with modern amenities, you can be sure you’ll be living in comfort during your time at the inn. Plus, our on-site restaurant is one of the best dining establishments in town, so you’ll be just steps away from delicious cuisine prepared with fresh local ingredients. Add our Lounge and the full bar to the mix, and you’ve got yourself the perfect recipe for a great night in the Berkshires.

Book your fall getaway with us today! We can’t wait to see you soon!

If you haven’t already, don’t forget to request your free copy of our Vacation Guide to the Berkshires! It will help you plan the ultimate getaway.