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Lenox Apple Squeeze

By September 19th, 2019 No Comments

The 40th annual Lenox Massachusetts Apple Squeeze
Two days, September 21 & 22, 2019


In addition to nearly 150 food, local business and craft vendors, we will again have games and shows for children, wagon rides around town, a 5k race, Children’s Olympics and much more. The 40th annual Lenox Massachusetts Apple Squeeze is a long-standing tradition in Berkshire County, ushering in the Fall season.

Join local shops, restaurants, artisans, musicians, farm stands, & performers as Lenox celebrates the apple harvest with a fun & engaging free street festival for all ages.

View All Vendors

Performance Schedule

Saturday11a-1pTerry A La BerryReading Park
Saturday1:30-2:30Rhythm KeepersReading Park
Saturday3:00-4:30Sunday StrummersReading Park
Saturday11:30-1:30Misty BluesMain Stage
Saturday2-4pmWhiskey CityMain Stage
Saturday4:30-6:30Born IV BluesMain Stage
Sunday11p-1pMatchstick ArchitectsMain Stage
Sunday1:30-3:30Rev TorMain Stage

This year’s Lenox Apple Squeeze will feature nearly 150 vendors spread out around downtown.

Arts and crafts abound at the Squeeze where you can explore tents full of unique items hand-crafted by talented artisans. Handmade jewelry, woven baskets, local soaps, quilts, photography, paintings, woodworks and much more will all be available.

But the biggest draw of all may be the food. Of course there is everything apple: pies, cakes, sauce, cider, donuts, muffins and even ice cream! Beyond that there is kettle corn, cakes slices over a foot tall, famous corn chowder, many food trucks and of course the always popular taco in a bag!

Also don’t forget to check out the great sidewalk sales, with big discounts, our local merchants have in their stores. Clothing, blankets, home goods, toys and even great artwork all can be found at once a year prices.

Images of past years

NEW! Apple Squeeze Scholarship!

This year at the 40th Lenox Apple Squeeze, a $1000 scholarship will be awarded to a Lenox senior. All Seniors are welcome to participate in the contest for the scholarship.

The contest details are as follows:

Post of photo on Instagram of the Apple Squeeze mascot Johnny Applesqueeze in a specific location around the historic district of Lenox with our specific hashtags:
The photos will be judged by the Chamber’s Apple Squeeze event committee as to which photo best captures the Fall spirit of Lenox.
Sign up by coming to the Lenox Visitor’s Center at 4 Housatonic Street (across from Loeb’s). The contest runs from Monday 9/9 thru Thursday 9/19. All entries must be posted by 9:00 pm on Thursday 9/19. The scholarship recipient will be announced at the Apple Squeeze on Saturday at the main stage from the live broadcast on Live 95.9.
For any further information, please contact the chamber office at or 413.637.3646