See all Pittsfield Christmas happenings this year!
Pittsfield prepares for Christmas 2025 in the historic district and downtown theaters, where classic architecture is trimmed in lights and wreaths. Programs showcase Christmas tours, seasonal festivals and winter celebrations, with craft markets, concerts and cozy events throughout the season.
Find the best Pittsfield Christmas happenings this year!
Top Christmas Events In and Around Pittsfield
- A Christmas Carol
- Stockbridge Main Street at Christmas (Stockbridge)
- Charles Dickens' A Christmas Carol at Ventfort Hall (Lenox)
- Winterlights at Naumkeag (Stockbridge)
- John Pizzarelli Big Band - Dear Mr. Sinatra (Great Barrington)
- Cows and Holly: Sandra Boynton's Christmas Album Explored (Great Barrington)
- Saratoga Springs Victorian Streetwalk Weekend (Saratoga Springs)
- Bright Nights at Forest Park (Springfield)
- Uptown Kingston Snowflake Festival (Kingston)
- Albany Santa Speedo Sprint (Albany)
See even MORE Christmas events below!
Pittsfield Christmas Events
Pittsfield Christmas Movies, Theater and Entertainment
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Step into the festive spirit with a captivating stage adaptation of Charles Dickens' 'A Christmas Carol.' This timeless story of redemption and holiday cheer is brought to life by the skilled performers of Berkshire Theatre Group. Experience the magic of Victorian London, the ghostly encounters, and the heartwarming transformation of Ebenezer Scrooge in a production that promises to be a memorable holiday tradition.
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Step back in time at Ventfort Hall for a special performance of 'A Christmas Carol,' presented by Gerald Charles Dickens, the author's own great-great-grandson. This intimate, one-man show brings the beloved holiday classic to life within the stunning Gilded Age mansion. Immerse yourself in the magic of the season and the rich history of this historic Lenox estate.
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Immerse yourself in the golden age of music with John Pizzarelli and his 17-piece big band as they present 'Dear Mr. Sinatra.' This electrifying performance pays homage to the legendary Chairman of the Board, Frank Sinatra, with a swinging celebration of his iconic songs. Prepare for a night of timeless melodies and exhilarating big band arrangements.
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Join cartoonist and songwriter Sandra Boynton for an engaging evening exploring her new Christmas album, 'Cows and Holly.' Hear about the album's creation, featuring songs performed by a star-studded lineup and spanning a variety of musical genres. Music videos from the album will also be screened.
Pittsfield Christmas Markets and Shopping
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Experience the magic of Stockbridge Main Street at Christmas, a beloved event that transforms this charming New England village into a festive wonderland. Inspired by Norman Rockwell's iconic "Home for Christmas" painting, the celebration features a historic property tour, a heartwarming holiday concert with sing-along, and a lively Main Street recreation complete with antique cars, carolers, Santa, and Mrs. Claus. Discover twinkling lights, holiday wreaths, and a spirit of simpler times.
Pittsfield Christmas Light Displays
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Experience the enchantment of Winterlights at Naumkeag, where thousands of shimmering, artfully designed holiday lights transform the landscape into a breathtaking spectacle. Wander through beautifully illuminated gardens and discover a magical winter wonderland perfect for creating lasting holiday memories.
Christmas Events Near Pittsfield
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With 20 years of experience, we use AI technology to build the most comprehensive list of christmas events events.
Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.
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