Upcoming Events in Pittsfield

The Lucky 5

11 December 2025

South Egremont, MA

The Egremont Barn, 17 Main St

SPINDLE (music bingo) w/ DJ Pup Daddy - Today's

11 December 2025

Lenox, MA

The Olde Heritage Tavern, 12 Housatonic St # 201

Tasting at Railroad Street Collective | Truffles

12 December 2025

Great Barrington, MA

25 Railroad St

Loneliness: Understanding and Healing the

09 December 2025

Stockbridge, MA

Kripalu Center For Yoga & Health, 57 Interlaken Rd

Annual Gingerbread House Decorating

14 December 2025

Otis, MA

Town Of Otis Parks & Recreation Commission, 70 N Main Rd

Winter Wonderland Family Fun Day

06 December 2025

Stockbridge, MA

Stockbridge Library Association, 46 Main St

Queer Men’s InterGen Self-Care Practice/Support

07 December 2025

Great Barrington, MA

401 Stockbridge Rd

Stockbridge Main Street at Christmas Recreation

07 December 2025

Stockbridge, MA

The Red Lion Inn, 30 Main St

Weekly Bird Walk Group

06 December 2025

Great Barrington, MA

Berkshire Food Co-op, 34 Bridge St

Hunter Andrus in Concert – MCC Coffeehouse Series

05 December 2025

Monterey, MA

Monterey Community Center, 468 Main Rd