Lenox Apple Squeeze
Kids can enjoy hayrides and face painting at the kids carnival, 10 a.m. to 5 p.m. Saturday in Lilac Park. Live music by Robin O'Herin, Rockridge Berkshire Bluegrass, Jaane Doe and more on Church Street, followed by a bonfire party at Apple Tree Inn.
Hancock Shaker Village Country Fair
Head to the annual Country Fair for live music, craft beer and cider, a quilt show, Shaker music and dancing, guided hikes, kids activities, crafts and more, Saturday and Sunday.
Get lost at Taft Farms
Head to Taft Farms to pick out your pumpkin, pick up a fresh hot cider donut, or to take a walk through the free corn maze.
Fall Fun at Ioka
Visit Ioka weekends through Oct. 30 to pick out your favorite pumpkin, wander through a mini corn maze, stop in at the animal petting area and more.
66th Annual Fall Foliage Parade
The fan-favorite annual parade returns Oct. 2!
Join the 54th Greylock Ramble then head to Ramblefest at the Adams Visitor Center. There will be live music, local craft beer and wine, food and craft exhibitors, a campfire and more. Historic Train Rides by Berkshire Scenic Railway will also be available.
Berkshire Botanical Garden's Harvest Festival
Berkshire Botanical Garden’s 87th annual Harvest Festival returns Oct. 8 and 9, with continuous live music and entertainment, food, vendors, a farmer’s market, pony and hayrides and more, 10 a.m. to 5 p.m.