The best things to do in Berkshire County

“GEAA Golf Course is a scenic 9-hole loop in Pittsfield with rolling fairways, pristine greens, and Berkshires views that make even a double feel poetic. Cap it off at Tavern at the A for generous pub grub and live local tunes.”

From the Berkshire County newsletter, September 14, 2026

“Based in the heart of the Berkshires, The Dessert Bar turns home-baked goodness into thoughtful gifts for that someone who has everything and dessert spreads for weddings and events. When you need a local baker who makes dessert feel personal, Gina Kelly’s treats are the kind you’ll plan a menu around.”

From the Berkshire County newsletter, September 9, 2026

“Just a mile from downtown Pittsfield, Mass Audubon Canoe Meadows Wildlife Sanctuary packs 253 acres and about three miles of mellow trails where warblers, turtles, ospreys, otters, and the occasional bear drop by. Perfect for a post-work reset or a weekend meander when you need woods without the drive.”

From the Berkshire County newsletter, September 18, 2026

“Ready Set Play is the Berkshires' only indoor playground, with ball pits, climbing structures, slides, trampolines and a full arcade, all kept sparkling with daily sanitizing. Let the 2-12 crowd burn energy this week while you grab a snack, chat with other parents, and feel zero guilt about the weather.”

From the Berkshire County newsletter, August 25, 2026

“Country Club of Pittsfield serves up a par-71, 18-hole Donald J. Ross layout from 1915, refreshed in 1931 by Wayne Stiles, that will challenge your eye and tempo. Members and guests can even browse Eric Mabee’s Golf Shop online with seasonal updates.”

From the Berkshire County newsletter, August 31, 2026

“Berkshire Hills Country Club is the only original A. W. Tillinghast design in Massachusetts, a beautifully groomed 18-hole course with panoramic views and a friendly, family vibe.”

From the Berkshire County newsletter, September 21, 2026

“Phoenix Theatres Beacon Cinema keeps Berkshire movie nights easy with first-run flicks, special events like Studio Ghibli Fest and Big Screen Classics, plus the occasional one-night-only surprise. When the week feels long, a proper, lights-down escape right in Pittsfield is the reset button you actually use.”

From the Berkshire County newsletter, August 27, 2026