Known for the abundance of cultural activities and events celebrated throughout the year, the Berkshires host dozens of annual summer and fall events that visitors look forward to all year. Tanglewood, of course, draws a huge crowd to the concert shed and lawn throughout the busy summer season. But Tanglewood isn’t the only game in town. Whether you’re a fan of music, dance, art, or theater, you’ll find a venue that caters to your passion in the hills of western Massachusetts. Annual events especially have a huge following. With a reputation for being the cultural hub of small to medium communities throughout the U.S., the Berkshires revel in celebrating everything from apples to ethnic films. Loyal followers of arts and craft festivals will want to plan a trip to visit us in both July and August. Hikers and fans of the harvest season flock to the hills in September and early October.
Every season has its highlights and reasons to consider a getaway. So, get out your calendars and get a jump on your summer and fall vacation planning with our handy guide to the annual summer and fall events in the Berkshires. We’d be delighted to have you stay with us at our quiet and cozy bed and breakfast in Sheffield, MA, conveniently located to enjoy all that our cultural mecca offers.
- LIme Rock Memorial Day Classic, May 22-25, 2020
- 33rd Season Berkshire Jewish Film Festival, Mondays July/August 2020
- 20th Annual Berkshires Arts Festival, July 3-5, 2020 at Ski Butternut
- Northeast Grand Prix, July 17-18, 2020
- Falcon Ridge Folk Festival, July 31-August 2, 2020
- 29th Annual Stockbridge Summer Arts and Crafts Festival, August 15 & 16, 2020
- Lime Rock Historics, September 3-7, 2020
- Lee Founders’ Weekend, September 10-13, 2020
- Housatonic Heritage Walks, September 12 & 13, 19 & 20, 26 & 27; October 3 & 4, 2020.
- 44th Annual Josh Billings Triathlon, September 13, 2020
- Lenox Apple Squeeze, September 26 & 27, 2020
- Fall Foliage Festival 2020, October 4, 2020
- Berkshire Botanical Harvest Festival, October 10-12, 2020
Don’t wait for a festival to book your room at the Staveleigh House Bed and Breakfast. Join us for our “Spring Special”— Stay 2 or more consecutive nights in April through May and save 20% off the regular room rate. Holiday weekends excluded.