Berkshires Annual Festivals 2021

After a long draught caused by the recent pandemic, the Berkshires lineup of annual festivals returns for 2021. Located in one of the most scenic areas of Massachusetts, the Berkshires host dozens of festivals annually. Many of our guests return year after year just to attend their favorite events and performances. Spring, summer, fall, and winter, there is always something fun to do when you visit us at the Staveleigh House Bed and Breakfast in Sheffield, MA.

Of course, the ever-present mansions, museums, and performing arts venues are carefully planning their own schedule of activities and events for 2021. Jacobs Pillow, Tanglewood, Shakespeare & Company, Mahaiwe Performing Arts Center, and other esteemed cultural meccas bring music, dance, and theater to the region throughout the year. We’ve assembled a preview of upcoming events planned to take place this year in the Berkshires. However, we recommend that you check each event’s website for accurate information and any planned schedule changes.

single yellow daffodil blooming on a background of green budsDaffodil and Tulip Festival at Naumkeag, April 22- May 16, 2021

Returning for its 3rd season, the Daffodil and Tulip Festival at Naumkeag is a welcomed harbinger of spring in the Berkshires. Stroll through acres of blooming daffodils and tulips planted throughout 8 acres of landscaped grounds at this gorgeous estate in the heart of Stockbridge.

Chester@Hancock, June-August, 2021

This season, the Chester Theatre Company has joined forces with Hancock Shaker Village to stage 3 productions this summer at the living history museum’s 750-acre property. Each performance, one each in June, July, and August, will be held outdoors in an open-air tent.

20th Annual Berkshires Arts Festival, July 2-4, 2021

Held at Ski Butternut in Great Barrington, MA, this juried art event is recognized as one of the country’s most respected cultural events of the season. Featuring 175 artists from across the country, the Berkshires Arts Festival presents extraordinary arts and crafts, entertainment, food, and live music.

Church on the Hill Fine Arts and Handmade Crafts Show, July 24-25, 2021

This annual event gathers the finest regional artisans for a juried event held in the center of Lenox, MA at the lovely Lilac Park. This is a free event open to the public, and is considered one of the bests art shows in the region.

Housatonic Heritage Walks, Sept 11 & 12, 18 & 19, 25 & 26 and Oct 2 & 3, 2021

Mark your calendars for 4 weekends of great hiking, historic walking tours, birding and nature walks throughout the upper Housatonic Valley National Heritage Area. Local historians, naturalists, and environmentalists offer free guided outings to explore and appreciated the natural surroundings of this spectacular region.

Lee Founders Weekend, September 17-19, 2021

Come out and join this quaint town’s annual birthday celebration. For 3 days in September, the town comes alive with food tastings, a street fair, parade, fireworks, and so much more. Fun for the whole family and a great way to welcome fall.

Ornate antique stage with red curtain and exquisite carvings. Berkshire Opera Festival, July-August 2021

Held at various esteemed venues throughout the region, this year’s festival kicks off at the McConnell Theater on the campus of Bard College with a presentation of Gloried Denied on July 22 and 24. Much Ado About Shakespeare will follow on August 11 at The Mount. The final production, Falstaff, takes place at the Mahaiwe Performing Arts Center in Great Barrington August 21-27, 2021.

Fall Foliage Festival, October 3, 2021

Join the fun at the annual Fall Foliage Festival held in in North Adams, MA. This well-loved festival kicks off with a parade through downtown on the first Sunday of October. The festivities continue throughout the week celebrating all things autumnal.

We’re looking forward to all of these great annual festivals and events. If you missed your favorite event last year, now is the time to mark your calendar, buy your tickets, and book your favorite room at our bed and breakfast in the Berkshires. We look forward to seeing you soon.