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The Lenox Chamber of Commerce is planning a full 2026 season of public events across Historic Lenox Village, with weekly markets, outdoor art shows, live music, downtown shopping events, and the 45th annual Lenox Apple Squeeze anchoring the calendar from late spring into early fall.
The season begins with the Lenox Farmers Market, which runs Fridays from May 22 through September 11 at St. Ann’s Parish. The market is scheduled for 11 a.m. to 3 p.m. and will feature regional farmers, bakers, wellness makers, artisans, flowers, prepared foods, handcrafted products, and live music.
Markets, Art, and Music
The Chamber’s warm-weather lineup also includes the Spring Art Walk on June 6 and 7, the Lenox Garden Party on June 20, and the Lenox Summer Arts Festival on July 11 and 12 in Lilac Park. The Art Walk brings regional artists and artisans into downtown Lenox, while the garden party is designed as a village-wide afternoon of shopping, dining, and seasonal experiences.
Music programming will return to Lilac Park with two free concert series. Lenox Loves Music is scheduled for Sundays in June and September at 3:30 p.m., while Concerts in the Park will take place Wednesdays in July and August at 6 p.m.
Apple Squeeze Returns in September
The fall schedule includes the Fall Art Walk on September 12 and 13 and the 45th annual Lenox Apple Squeeze on September 26. Apple Squeeze, one of the village’s signature events, is expected to feature more than 100 artisan and food vendors, live music, family activities, and a downtown street fair atmosphere.
The Chamber describes the season as part of Lenox’s ongoing effort to bring together residents, businesses, artists, and visitors through accessible, walkable programming in the village center. Full event details and updates are available at lenox.org.








