11 Oct All Day Chesterwood: Ann Jon’s A Retrospective Chesterwood 3 Williamsville Road, Stockbridge Event Details Get Directions Exhibits
11 Oct All Day Rally for Recovery Pickleball Tournament Bousquet Sport 100 Dan Fox Drive, Pittsfield Event Details Get Directions Benefits and Galas, Health and Wellness
11 Oct All Day Fall Foliage Train Rides Berkshire Scenic Railway 3 Hoosac Street, Adams Event Details Get Directions Family Friendly, History and Heritage
11 Oct 8:00 am - 5:00 pm Rocky Horror Show 50th Anniversary Phoenix Theatres Beacon Cinema 57 North Street, Pittsfield Event Details Get Directions Performing Arts & Entertainment
11 Oct 9:00 am - 1:00 pm Pittsfield Farmers’ Market The Common 100 1st Street, Pittsfield Event Details Get Directions Farmers' Markets
11 Oct 10:00 am - 3:00 pm Sweetwood Fall Festival SweetWood of Williamstown 1611 Cold Spring Road, Williamstown Event Details Get Directions Belong Berkshires, Family Friendly, Festivals, Outdoor Event
11 Oct 10:00 am - 5:00 pm Blacksmithing Workshop Hancock Shaker Village 1843 West Housatonic Street, Pittsfield Event Details Get Directions
11 Oct 10:00 am - 5:00 pm Harvest Festival Berkshire Botanical Garden 5 West Stockbridge Road, Stockbridge Free – $15 Event Details Get Directions Belong Berkshires, Family Friendly, Festivals, Food and Drinks, Outdoor Event
11 Oct 11:00 am - 3:00 pm Second Saturdays for Families Norman Rockwell Museum 9 Route 183, Stockbridge Event Details Get Directions Exhibits, Family Friendly
11 Oct Featured 12:00 pm - 5:00 pm RambleFest 2025 Adams Visitor Center 3 Hoosac Street, Adams Event Details Get Directions