Attention all locals and soon-to-be-locals to Lenox: the Apple Squeeze is back for its 44th year.
The free-to-attend festival attracts families, locals on dates, and visitors looking for a fun shopping spree. 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 27th from 10 am to 5 pm. The Squeeze takes place throughout historic downtown Lenox, along Main Street and Church Street, along with the nearby Lilac Park. Lenox has scheduled Sunday, September 28 as the event’s rain date.
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 2025 Apple Squeeze?
The Apple Squeeze hosts a number of musicians throughout downtown through the course of the day. The drum group Berkshire Rhythm Keepers will start the day, followed by consecutive performances by local favorites Colby Lewis & Steve Ide, and Jordan Weller & The Feathers. The final performance by the Happy Together band has become something of an Apple Squeeze staple.
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 find a bounce house or two to keep the kiddos occupied, plus a bake sale by the Morris Elementary School PTO. It’s likely that the Chamber will include a balloon twister or face painter again as they have in previous years, as well.
Vendors at The Apple Squeeze
The Apple Squeeze has garnered a wide variety of vendors to populate its streets throughout the past four decades. The Squeeze’s food vendors include Antimony Brewing, who will set up a beer garden. You can get a full meal from vendors like La Chalupa or Gunther’s Sausage Wagon. If you’re looking for a sweet treat, the options are endless: Shire Donuts, Tara’s Truffles, Bear Butter, Mazz’s Kettle Korn and Berkshire Canoli Company have all been announced as vendors with more to come. As you wander, you can expect to find clothing, jewelry, knicknacks, fine art and more. You never know what treasures are awaiting you within the shops and booths of Lenox.
