Attention all locals and soon-to-be-locals to Lenox: the Apple Squeeze is back for its 45th 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, updated for 2026, below.
When is the Apple Squeeze in Lenox?
This year’s Apple Squeeze will occur on Saturday, September 26th 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.
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 2026 Apple Squeeze?
The Apple Squeeze hosts a number of musicians throughout downtown through the course of the day. This year, the organizers have named the Central Station Courtyard (next to Town Hall) as the musical epicenter. Local jazz-fusion band TNT+ begins the music at 11 a.m., with consecutive performances by Americana bands Rounders Revival and Whistle & The Stack. The drum group Berkshire Rhythm Keepers also returns for another year with a show at Roche Reading Park at 12:30 p.m.. BeatNest, a local electronic music programming, will have their students perform a showcase in Lilac Park at 1 p.m.. At Sugar Magnolia, Lenox's newest sweet spot, DJ Bland and DJ Secret Hideaway will play a set at 2 p.m..
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; it's the designated kid's play area each year. You’ll likely find a bounce house or two to keep the kiddos occupied, or a balloon twister or face painter.
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 Mary's Kitchen, Naji's Meditteranean, or Gunther’s Sausage Wagon. If you’re looking for a sweet treat, the options are endless: Shire Donuts, Modern Milk Bar, Bear Butter, Mazz’s Kettle Korn and High Lawn Farm and more all set to appear. Jake's Java will set up for another caffeinated option to the brick-and-mortar coffee shops in town. 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.
What is it Like to Live in Lenox?
As a real estate professional, I specialize in creating media that helps you picture your new life in Berkshire County. You can watch my YouTube video on Breaking Down the Berkshires below to see if Lenox, or another part of the Berkshires, is the best fit for your lifestyle. If you have any specific questions, I'd love to help–get in touch any time.
