Everyone in New England knows that this time of year in the Berkshires always feels magical. The vibrant fall foliage, coupled with multiple art events and complemented by renowned museums, makes this place a go-to every fall. And fall 2025 is hardly an exception.
The stunning natural beauty of this region is a must-see this season. However, if the drive down Mohawk Trail is not enough, you can maximize your experience by diving deeper into planning.
Take a closer look at things to do this fall in the Berkshires.
Why the Berkshires Shine in the Fall
The Berkshires truly come alive in the fall. The mountains and valleys turn into a red, orange, and gold canvas. Even a simple drive down the local road can turn into a breathtaking experience.
While famous for the nature spots, the Berkshires also stand out for their rich culture. You can complement your trip by visiting such famous museums as the Clark Art Institute and MASS MoCA. They host exhibits and events that attract visitors from all over New England and beyond. Meanwhile, local theaters present fall performances that blend art with the season’s charm.
If you love family events, the Berkshires won’t disappoint. From farmers’ markets filled with fresh harvest goods to craft fairs and music festivals, you’ll always find something happening in the area.
Top Berkshire Fall Events
Whether you’ve been in the Berkshires before or just plan to visit for the first time, here are a few must-attend Berkshire fall events.
- WIT Literary Festival 2025 (Sept 25–28): A weekend of author talks and conversations in the Berkshire Hills.
- A Living History Weekend at the Bidwell House Museum (Oct 4–5): A step into Revolutionary-era life with reenactments and historic talks.
- 69th Annual Fall Foliage Parade (Oct 5): A festive, family-friendly parade through downtown North Adams, celebrating autumn with a space-themed twist. This year’s theme is “To Northern Berkshire & Beyond.”
- Celebrating Jewish Plays (Oct 10–12): Theater performances of Jewish-themed plays at Shakespeare & Company.
- Berkshire Mobile Farmers’ Market (runs until Oct 17): A roaming market offering fresh local produce and pantry staples
If you are a cannabis enthusiast who knows the value of an excellent experience, you should stock up on discreet products. Attending these events with quality cannabis products, such as edibles or vapes, can make these moments even richer.
Outdoor Activities in Berkshires
Leaf peeping is a major part of the Berkshires’ fall events. If you are planning to attend a festival or go to a concert, you can take the scenic route to the destination. The colors you will see definitely warrant a slight detour. Here are the routes to consider:
- Mohawk Trail West (Greenfield to North Adams): Points of interest include Rocky Mountain Park, Bridge of Flowers, and Mohawk Trail State Forest.
- Connecticut River Scenic Byway in the Pioneer Valley: Points of interest include The Amazing World of Dr. Seuss Museum, Mount Holyoke College Botanic Garden, and Quabbin Reservoir.
If you want to add some special family fun to your trip, make sure to check out the apple-picking spots along the way. We recommend visiting Bartlett’s Orchard, which is great for picking apples and pumpkins. You can also stop by High Lawn Farm and pet the cows.
Community Events Worth Attending
This fall offers people who live in the Berkshires an excellent opportunity to connect with the community. To visit the local fairs and markets, you don’t even have to plan a long trip. If you feel like enjoying some community time, here are a few events to check out:
- Lee Founders Weekend (Sept 19–21): Celebration of Lee’s history with parades, live music, food vendors, and fireworks.
- Fall Festival at St. Paul’s (Sept 27): A community event featuring gift basket raffles, vendors, plants, a bake sale, and a café at St. Paul’s Episcopal Church.
- The Great Holyoke Brick Race (Oct 11): Design and race a brick racecar in this creative and fun gravity-powered race on Race Street
- Berkshire Botanical Garden Harvest Festival (Oct 11–12): A weekend of artisan vendors, local food, live music, and family activities.
Visit Canna Provisions in Lee & Holyoke
This year, the Berkshires’ fall events are especially creative. You can choose from a wide variety of activities that keep each fall weekend full of excitement. If you are a cannabis enthusiast who wants to improve your fall experience, we invite you to visit our Lee dispensary and Holyoke dispensary.
If you’d like to plan your adventure in advance, we recommend consulting our virtual budtender at any convenient time.
Plan your Berkshire adventure with a stop at Canna Provisions!
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