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!
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Top Holiday Events In and Around Pittsfield
- Bright Nights at Forest Park (Springfield)
- A Christmas Carol (Stockbridge)
- Downtown Stockbridge Holiday Season (Stockbridge)
- It’s a Wonderful Life (Great Barrington)
- John Pizzarelli Big Band (Great Barrington)
- Charles Dickens’ A Christmas Carol at Ventfort Hall (Lenox)
- Festival of Trees NOSTALGIA
- The Wizard of Oz (Great Barrington)
- Cows and Holly with Sandra Boynton (Great Barrington)
See these and even more events listed below!
Pittsfield Holiday Light Displays
Bright Nights at Forest Park
What to Expect:
Unique public-private collaboration with over 7 million visitors.
Description:
Bright Nights at Forest Park is a three-mile drive-thru spectacle featuring over 700,000 lights, iconic characters, and peaceful gardens, all illuminated for a joyous holiday experience.
Where: Springfield | More Info: Bright Nights at Forest Park
Pittsfield Holiday Shows and Entertainment
A Christmas Carol
What to Expect:
Sensory-friendly performance available.
Description:
A timeless adaptation of Charles Dickens' classic tale, A Christmas Carol, follows Ebenezer Scrooge as he is visited by four spirits, guiding him on a transformative journey through Victorian England. This heartwarming production is filled with holiday carols and the wonder of the season.
Where: Stockbridge | More Info: A Christmas Carol
Charles Dickens’ A Christmas Carol at Ventfort Hall
What to Expect:
One-man theatrical performance with 26 characters.
Description:
British actor Gerald Charles Dickens presents a one-man theatrical performance of Charles Dickens' classic work, "A Christmas Carol," at Ventfort Hall. Using his own adaptation, Gerald plays 26 characters, bringing each scene vividly to life. The event includes an elegant tea following the performance.
Where: Lenox | More Info: Charles Dickens’ A Christmas Carol at Ventfort Hall
Cows and Holly with Sandra Boynton
What to Expect:
Grammy-nominated Sandra Boynton's diverse Christmas album with various musical styles.
Description:
Cartoonist, writer, and songwriter Sandra Boynton presents her latest album/songbook, Cows and Holly, featuring a diverse range of Christmas classics from 60s Surf Rock to Broadway and Folk-Country, performed by notable artists like Zooey Deschanel and Yo-Yo Ma. The event includes a conversation with WAMC's Joe Donahue and screenings of music videos created by Boynton and her collaborator, Michael Ford.
Where: Great Barrington | More Info: Cows and Holly with Sandra Boynton
John Pizzarelli Big Band
What to Expect:
Tribute to Frank Sinatra with a 17-piece big band.
Description:
John Pizzarelli Big Band performs a tribute to Frank Sinatra with an 17-piece big band, playing iconic songs like "Witchcraft," "Wee Small Hours," and "Ring a Ding Ding," along with signature Sinatra arrangements.
Where: Great Barrington | More Info: John Pizzarelli Big Band
The Wizard of Oz
What to Expect:
Classic 1939 film screening with community tradition.
Description:
Join Dorothy, Toto, the Tin Man, Scarecrow, and the Cowardly Lion in this classic 1939 musical favorite about friendship, courage, and adventure as they journey home.
Where: Great Barrington | More Info: The Wizard of Oz
It’s a Wonderful Life
What to Expect:
Free screening of a classic holiday film.
Description:
The classic film "It's a Wonderful Life" (1946) starring Jimmy Stewart as George Bailey, a troubled soul visited by his guardian angel, is screened free at the Mahaiwe Performing Arts Center. This annual tradition celebrates the holiday season with a timeless story of impact and redemption.
Where: Great Barrington | More Info: It’s a Wonderful Life
Downtown Stockbridge Holiday Season
What to Expect:
Recreates Norman Rockwell's iconic holiday scene with vintage cars.
Description:
Downtown Stockbridge transforms into a charming New England setting adorned with holiday wreaths and festive lights. The town celebrates with live performances, historic property tours, holiday markets, and unique shops. The event culminates on Sunday with a recreation of Norman Rockwell's famous holiday scene, featuring vintage automobiles and festive activities.
Where: Stockbridge | More Info: Downtown Stockbridge Holiday Season
Pittsfield Other Holiday Activities
Festival of Trees NOSTALGIA
What to Expect:
Community-built holiday decorations with a nostalgic theme.
Description:
The Festival of Trees Nostalgia at the Berkshire Museum is a cherished community tradition celebrating its 39th year. This year's theme, "Nostalgia," features beautifully decorated trees and ornaments that evoke memories of past holidays. The event showcases a blend of traditional and modern holiday decorations, creating a warm and inviting atmosphere.
Where: Pittsfield | More Info: Festival of Trees NOSTALGIA
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Albany (30 miles)
- Troy (30 miles)
- West Albany (32 miles)
- Northampton (32 miles)
- Latham (33 miles)
- Westfield (34 miles)
- Holyoke (36 miles)
- Amherst (38 miles)
- North Chicopee (38 miles)
- Chicopee (39 miles)
- Clifton Park (39 miles)
- West Springfield (40 miles)
- Springfield (41 miles)
- Agawam (42 miles)
- Schenectady (43 miles)
- Rotterdam (44 miles)
- West Torrington (44 miles)
- Ludlow (44 miles)