Celebrate the festive wonders of Pittsfield with our ultimate guide. From hometown residents to holiday guests, our guide reveals the best of Pittsfield's festive season.
Popular Events: Enjoy the enchanting display of lights and festive spirit at Bright Nights at Forest Park, where families gather to admire the holiday magic. Another highlight is A Christmas Carol, a timeless tale that captivates audiences with its heartfelt storytelling and memorable characters. And the Downtown Stockbridge Holiday Season is something you definitely don’t want to miss, featuring charming shops and delightful seasonal activities. See more details on these and other fun events and activities below!
Happy Holidays!
Top Events Events In and Around Pittsfield
- A Christmas Carol at Berkshire Theatre Group
- Nutcracker! Magical Christmas Ballet
- NUTCRACKER! Magical Christmas Ballet
- Charles Dickens' A Christmas Carol at Ventfort Hall (Lenox)
- WinterLights at Naumkeag (Stockbridge)
- Winterlights at Naumkeag and Eleanor Cabot Bradley Estate (Stockbridge)
- Stockbridge Main Street at Christmas (Stockbridge)
- Stockbridge Main Street at Christmas (Stockbridge)
- Cows and Holly with Sandra Boynton (Great Barrington)
- John Pizzarelli Big Band: Dear Mr. Sinatra (Great Barrington)
🎃 Explore all 10+ featured events below!
Pittsfield Events Events
A Christmas Carol at Berkshire Theatre Group (Pittsfield) • 0.5 miles
Classic holiday tale brought to life on stage
Nutcracker! Magical Christmas Ballet (Pittsfield) • 0.5 miles
A holiday spectacular with international theatrical traditions.
NUTCRACKER! Magical Christmas Ballet (Pittsfield) • 0.5 miles
Opulent sets, costumes, and international cast
Charles Dickens' A Christmas Carol at Ventfort Hall (Lenox) • 7.0 miles
A classic holiday tale brought to life in a historic mansion.
WinterLights at Naumkeag (Stockbridge) • 11.7 miles
Thousands of shimmering, artfully designed holiday lights
Winterlights at Naumkeag and Eleanor Cabot Bradley Estate (Stockbridge) • 11.7 miles
Thousands of shimmering, artfully designed holiday lights.
Stockbridge Main Street at Christmas (Stockbridge) • 12.1 miles
A charming New England village transformed into a holiday wonderland.
Stockbridge Main Street at Christmas (Stockbridge) • 12.1 miles
A charming New England village transformed into a Rockwellian Christmas scene.
Cows and Holly with Sandra Boynton (Great Barrington) • 18.7 miles
New Christmas album and songbook presentation
John Pizzarelli Big Band: Dear Mr. Sinatra (Great Barrington) • 18.7 miles
A 17-piece big band saluting Frank Sinatra
The Wizard of Oz Screening (Great Barrington) • 18.7 miles
A beloved community tradition screening of a classic film.
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