Berkshire County Annual Events
Berkshire County is home to a vibrant array of annual events that celebrate the region’s culture, arts, food, and outdoor beauty. From music festivals to farm-to-table feasts, there’s always something happening to capture your attention no matter the season. These yearly events bring together locals and visitors alike, creating a unique sense of community in the heart of the Berkshires.
Tanglewood Music Festival (June–August)
Tanglewood is the summer home of the Boston Symphony Orchestra and a world-renowned music festival. Held in Lenox, this event features performances from classical music’s greatest talents as well as contemporary artists, all performed in a stunning outdoor setting. Whether you’re picnicking on the lawn or sitting in the famed Koussevitzky Music Shed, Tanglewood is a must for any music lover visiting the Berkshires in the summer.
Berkshire International Film Festival (May/June)
The Berkshire International Film Festival (BIFF) is a premier event that showcases independent and international films. Hosted in Great Barrington and Pittsfield, BIFF brings together filmmakers, actors, and cinema enthusiasts for screenings, panel discussions, and exclusive events. It's a fantastic opportunity to catch cutting-edge films and meet industry leaders in the scenic Berkshires.
Fall Foliage Parade (October)
The annual Fall Foliage Parade in North Adams is one of the Berkshires’ most beloved traditions. Held during peak foliage season, this event features colorful floats, local bands, and plenty of community spirit. It’s a family-friendly event that celebrates the natural beauty of the region as the leaves change into stunning autumn colors.
Williamstown Theatre Festival (July–August)
The Williamstown Theatre Festival is a celebrated annual event that draws families and theater lovers alike. Held each summer, the festival showcases world-class productions, from classic plays to modern debuts. Children and adults can enjoy a range of performances, workshops, and community events, making it a perfect cultural outing for families in the Berkshires.
Berkshire Crafts Fair (August)
The Berkshire Crafts Fair in Great Barrington is one of the region’s top art and craft shows. Featuring handmade works from over 100 artisans, the fair showcases jewelry, ceramics, textiles, and more. It’s the perfect event for art enthusiasts and those looking for unique, handcrafted items to take home as souvenirs.
Jacob's Pillow Dance Festival (June–August)
Jacob's Pillow Dance Festival is the longest-running dance festival in the United States, held annually in Becket. The event features performances by world-class dance companies and offers workshops, talks, and behind-the-scenes tours. Jacob’s Pillow is a dance lover's paradise, providing a chance to see cutting-edge and traditional dance forms in an idyllic, rural setting.
Berkshire Mountain Distillers Craft Spirits Festival (September)
The Berkshire Mountain Distillers Craft Spirits Festival is an event not to miss for craft spirits enthusiasts. Held at the distillery’s grounds in Sheffield, this festival features tastings of locally distilled spirits, food trucks, live music, and tours of the facility. It’s a fun and lively event that celebrates the burgeoning craft beverage scene in the Berkshires.
Stockbridge Main Street at Christmas (December)
Stockbridge Main Street at Christmas is an annual event that transforms the town into a festive scene straight out of a Norman Rockwell painting. With vintage cars, horse-drawn carriage rides, and holiday-themed activities for families, this event is a nostalgic celebration of the holiday season. It’s the perfect way to experience small-town charm while getting into the Christmas spirit.
Shakespeare & Company (May–October)
Shakespeare & Company in Lenox is a premier venue for theater enthusiasts, offering world-class productions of Shakespeare’s plays as well as contemporary works. The company’s season runs from May to October, featuring outdoor and indoor performances, making it an essential stop for anyone interested in the arts during a visit to the Berkshires.
The Sheffield Fair (August)
The Sheffield Fair is a summer event that combines agricultural exhibits, local food, crafts, and live entertainment. Held at the Sheffield Town Park, it’s a family-friendly event where you can enjoy everything from a pie-eating contest to farm animal shows. The fair highlights the agricultural heritage of Berkshire County.
Lenox Apple Squeeze (September)
The Lenox Apple Squeeze is a celebration of the apple harvest, a long-standing tradition in this historic town. The event features apple-inspired foods, local vendors, live music, and family activities along the streets of downtown Lenox. It’s the perfect way to welcome the fall season in the Berkshires with cider donuts, apple pies, and local farm produce.
Berkshires Arts Festival (July)
The Berkshires Arts Festival is an annual event that draws some of the finest artists and craftspeople from across the country. Held in Great Barrington, this juried show features contemporary arts and crafts, including paintings, sculptures, photography, and handmade furniture. Art lovers can peruse hundreds of exhibits while enjoying live music and food from local vendors.
These annual events capture the diverse culture and charm of Berkshire County, offering something for everyone, from arts and crafts to music, film, and food. Whether you're visiting for a specific event or looking to experience the region's year-round festivities, the Berkshires never disappoints.