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7 fall fun events not to miss in the Berkshires

Lenox Apple Squeeze 

bushel of apples on a busy street full of vendors

Visitors and vendors pack the streets of downtown Lenox for the annual 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

A group of people sit under a tree with looms

Spinning yarn under the shade of a large tree on the grounds during the annual 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

People in red wander a maze, seen from overhead

The corn maze at Taft’s Farms in Great Barrington in 2020.

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

People in a field of pumpkins

People pick out pumpkins at Ioka Valley Farm in Hancock.

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 


Children stand along Main Street to watch the 64th Annual Fall Foliage Parade in 2019.

The fan-favorite annual parade returns Oct. 2!



Man and woman serve beer

Suzy Helme and Tim Martin serve up craft beer from Bright Ideas Brewing during Ramblefest in Adams in 2019.

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

Children sit on a lawn

A crowd watches a puppet show during the 2020 Harvest Festival at Berkshire Botanical Garden.

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.  


Meggie Baker can be reached at mbaker@berkshireeagle.com or 413-496-6207. 

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