Festivals and Annual Events in the Berkshires

Known for the arts and wonderful outdoor attractions, the Berkshires also are home to numerous fairs, festivals, and annual events.

Berkshire Crafts Fair

The annual Berkshire Crafts Fair in Great Barrington, MA is a juried show of master artisans. You will find ceramics, furniture, glassware, jewelry, textiles, woodwork, and more. The fair is typically held in August.

Berkshire Crafts Fair
600 Stockbridge Road
Great Barrington, MA 01230


Berkshire International Film Festival

The Berkshire International Film Festival presents the latest in independent feature, documentary, short, and family films. It also includes panel discussions and special events. Films and events are in Great Barrington and Pittsfield. The festival happens in the late spring.

Berkshire International Film Festival
PO Box 237
Great Barrington MA 01230
Phone: 413-528-8030


Berkshire Jewish Film Festival

The Berkshire Jewish Film Festival is held annually starting in July and running into August. All films are shown at the Duffin Theater at Lenox Memorial High School at 197 East Street in Lenox MA. The festival is the creation of Congregation Knesset Israel in Pittsfield.


Chocolate Berkshires

Chocolate Berkshires is a month-long celebration of chocolate. Chocolate themed and other events happen throughout February at various businesses throughout the Berkshires.


Fall Foliage Festival

The Northern Berkshire Fall Foliage Festival and Parade is an annual celebration of fall that happens in October in downtown North Adams, MA.


Festival Of Trees

The Festival Of Trees is an annual holiday celebration at the Berkshire Museum. Great fun for the whole family, the festival runs from mid-November to January 2.

At The Berkshire Museum
39 South Street (Route 7)
Pittsfield, MA 01201
Phone: 413-443-7171


Lee Founder’s Weekend

Lee Founder’s Weekend is an annual celebration of the founding of Lee, Massachusetts.


Lenox Caroling Festival

The annual Lenox Caroling Festival starts appropriately with a tree lighting. There is also a day-long caroling concert and Lenox is decked out in “old fashioned holiday splendor”. The festival takes place in early December.


Memorial Day Marathon Races

Boston may have its marathon, but the Berkshires have their Memorial Day Marathon through Lenox, Stockbridge and Great Barrington, MA complete with their own hill – in this case Prospect Hill. There are actually multiple races: a marathon, half marathon, 10K, 5K, tail race, and a kids run.


North Adams Open Studios Weekend

North Adams, MA hosts an annual Open Studios Weekend every year in October.


Rock, Rattle & Drum Pow Wow

The annual Rock, Rattle & Drum Pow Wow is a weekend of American Indian music, dance, education, entertainment, and cultural festivities, There are also arts and crafts vendors. This is great fun for the whole family! The festival is held in August.


Williamstown Film Festival

Founded in 1998, the Williamstown Film Festival presents films and other events in Williamstown, MA in the fall.

Williamstown Film Festival
Box 81
Williamstown, MA 01267
Phone (tickets): 413-458-9900


West Stockbridge Zucchini Festival

The annual West Stockbridge Zucchini Festival features parades, food, craft booths, music, fireworks, and more. The festival takes place in August.

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