Annual Events
Discover all the annual events in the Berkshires of Western Massachusetts! From cultural festivals and outdoor adventures to performances and holiday celebrations, explore year-round activities for every interest.
Pillow Pride at Jacobs Pillow. Photo by Hayim Heron
Fall
Housatonic Heritage Walks
Berkshire County Historial Society Community Day
Hancock Shaker Village Country Fair
FreshGrass
Lee Founders Weekend
Lenox Apple Squeeze
PMC Unpaved
Housatonic Heritage Walks
Fall Foliage Parade
Fall Jazz Sprawl
Berkshire Botanical Garden Harvest Festival
Naumkeag Pumpkin Show
Bousquet Oktoberfest
Hancock Shaker Village Community Day
RambleFest
Events in the Berkshires
In the Berkshires, there is always something to do! Search our full calendar of events happening during your stay #intheberkshires.