𝐍𝐞𝐱𝐭 𝐞𝐝𝐢𝐭𝐢𝐨𝐧: September 25 – 27, 𝟐𝟎𝟐6 

There’s something special about autumn in Lenox.

As the streets fill with artisan vendors, live music, fresh cider, and the unmistakable scent of apple cider donuts, the Lenox Apple Squeeze becomes more than a festival—it’s a celebration of everything we love about fall in the Berkshires.

Berkshires Untold invites you to experience one of our most cherished local traditions. Enjoy the the festivities in Lenox and a few special treats here at Berkshires Untold:

From September 25–27, we’ve created an autumn escape that captures the warmth, flavor, and simple joys of the season. Begin your stay with your choice of a complimentary Warm Spiced Apple Cider or an Apple Bourbon Welcome Cocktail, then spend the day exploring downtown Lenox with our curated Apple Squeeze Walking Guide, featuring festival highlights, favorite artisan vendors, local shops, hidden gems, and our can’t-miss food stops.

Wake up to harvest-inspired breakfast favorites including Apple Cinnamon Pancakes, Brioche French Toast with Maple Apples, fresh local apples, warm cider, apple cider donuts, and seasonal coffee specials.

After a day at the festival, return to Berkshires Untold and unwind with seasonal desserts like Warm Apple Crisp à la Mode, Apple Pie Cheesecake, Salted Caramel Apple Tart, or gather around the fire pits for our Signature S’mores Flight, perfectly paired with warm cider or one of our seasonal cocktails.

Because the best part of Apple Squeeze weekend isn’t just what happens downtown—it’s having a place where the celebration continues long after the festival ends.

Join us September 25–27 – rooms often fill up by late August!