
THE PERFECT SEPTEMBER TRIP
Afternoon attend local festivals happening in September:
Lee’s Founders Weekend (around Sept 19–21): parade, food vendors, fireworks Visit the Berkshires of Western MA
Lenox Apple Squeeze (≈Sept 27): music, carnival, apple treats New England Wanderlust+3Visit the Berkshires of Western MA+3wit & whimsy+3
Hancock Shaker Country Fair (Sept 27–28): crafts, quilts, farm animals
September events dates: Founders Weekend (Sept 19–21), Lenox Apple Squeeze (Sept 27), Hancock Fair (Sept 27–28) Edible Berkshires+8Visit the Berkshires of Western MA+8Adventurous Kate+8
WIT Literary Festival, Sept 25–28 in Lenox & Great Barrington Wikipedia+2Berkshire Style+2Wikipedia+2
Berkshire Opera Festival often presents pop-up performances throughout September Visit the Berkshires of Western MA+1Visit the Berkshires of Western MA+1
Check for “Cocktails in Great Gardens” evening social events at the Botanical Garden on select Fridays in September Berkshire Botanical
Evening (Sept 19–21): Unwind to bluegrass at FreshGrass Festival at MASS MoCA in North Adams
Valid until September 30, 2025
Subject to availability & blackout dates.