The best things to do in Berkshire County

6 things to do we’ve checked and stand behind — with the story on each one. Not a ranking; a record.

Browse another shelf: all of Berkshire County’s best · Restaurants · Arts & Culture · Beauty · Bakeries & Sweets · Sporting Goods · Shopping · Hobbies, Books, & Crafts · Home & Garden · Nightlife

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Entertainment · 6 places · showing the latest additions first

GEAA Golf Course

Entertainment

GEAA Golf Course is a scenic 9-hole loop in Pittsfield with rolling fairways, pristine greens, and Berkshires views that make even a double…

303 Crane Ave (Pittsfield)

“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.”

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Dessert Bar

Entertainment

Based in the heart of the Berkshires, The Dessert Bar turns home-baked goodness into thoughtful gifts for that someone who has everything…

11 Lexington Pkwy (Pittsfield)

“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, August 6, 2026

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Mass Audubon Canoe Meadows Wildlife Sanctuary

Entertainment

Nature preserve with trails for hiking, cross-country skiing and wildlife-watching.

309 Holmes Rd (Pittsfield)

“Nature preserve with trails for hiking, cross-country skiing and wildlife-watching.”

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Ready Set Play

Entertainment

Clean and spacious indoor space with slides, jungle gyms and ball pits for toddlers through older kids.

675 Merrill Rd (Pittsfield)

“Clean and spacious indoor space with slides, jungle gyms and ball pits for toddlers through older kids.”

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Berkshire Hills Country Club

Entertainment

Country club with a golf course that hosts weddings, anniversaries, and other events.

500 Benedict Rd (Pittsfield)

“Country club with a golf course that hosts weddings, anniversaries, and other events.”

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Phoenix Theatres Beacon Cinema

Entertainment

This independent movie theater with stadium seating screens first-run films & offers beer & wine.

57 North St (Pittsfield)

“This independent movie theater with stadium seating screens first-run films & offers beer & wine.”

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