Lenox Apple Squeeze 2023: Everything you Need to Know

Attention all locals and soon-to-be-locals to Lenox: the Apple Squeeze is back for its 42nd year. The one-day festival returned for the first time since the pandemic last year, and is sure to delight for dates, shopping sprees and family outings. Learn more about this classic yearly tradition below. 

When is the Apple Squeeze in Lenox?

This year’s Apple Squeeze will occur on Saturday, September 23rd from 10 am to 5 pm. The Squeeze takes place throughout historic downtown Lenox, along Main Street and Church Street. 

Lenox MA

What is the Apple Squeeze?

The Apple Squeeze has been part of life in Lenox since its inception in 1979. Call it a block party, craft fair, or a leaf-peeping extravaganza; you’ll find delicious food, interesting works of art, and live music around every corner. Local nonprofit organizations and entertainment for kids of all ages are always sure to make an appearance. The event closes out the busy summer season in downtown Lenox and ushers in fall with treats like candy apples and chowder. Best yet, you can take a walk away from the action and window shop for your next home in the idyllic neighborhoods that surround downtown. 

Who will be playing the 2023 Apple Squeeze?

The Apple Squeeze hosts a number of musicians throughout downtown. In the past two years, Berkshire Busk! has taken over booking the performers. Headliners for this year’s squeeze include the Happy Together Band, bluegrass group The Juckets, blues artist David Reed and up-and-coming duo Kajax. 

Family Events 

The Apple Squeeze is a great event to bring your kids along to. Pick up a bag of popcorn or cotton candy ahead to Lilac Park on Main Street; you’ll typically find a bounce house or two to keep the kiddos occupied. The Berkshire Rhythm Keepers led by Aimee Gelinas of Tamarack Hollow will showcase student drummers at the park in the afternoon. 

Vendors at The Apple Squeeze

The Apple Squeeze has garnered a wide variety of vendors to populate its streets throughout the past four decades. As you wander, you can expect to find clothing, jewelry, knicknacks, fine art, baked goods and more. You never know what treasures are awaiting you within the shops and booths of Lenox.

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