Your Guide to a Festive December
There’s nothing quite like December in Bennington. Snow-covered evergreens, warm lights twinkling along Main Street, and the kind of small-town charm that makes the holiday season feel truly magical. Thanks to excellent plowing by the Town of Bennington, our downtown stays walkable, drivable, and safe, making it easy to explore, shop, and celebrate all month long.
Bennington is home to local businesses and community traditions that make the holidays shine. And with December right around the corner, we’re excited to share a festive lineup of fun, family-friendly holiday events happening here in southern Vermont. If you haven’t found your holiday spirit yet, now’s the perfect time to get out and enjoy everything Bennington has to offer, from tours and concerts to tree lightings, Santa visits, and more.
Here’s what’s happening in Bennington, Vermont this holiday season.
A Friendly Reminder: Shop Local This Holiday Season
Before we jump into the festivities, we want to offer a gentle reminder about the value of shopping local. In our November blog post, we shared a full guide to Bennington’s best local destinations for unique, meaningful gifts, the kind you just can’t find anywhere else.
Supporting our small businesses keeps our community strong, vibrant, and resilient. And as winter arrives, we’re also excited to see how the snow interacts with Bennington’s new public art installations, adding another layer of beauty to our downtown experience.
Holiday Events in Bennington
Events are listed in chronological order for easy planning.
Friday–Sunday, December 5–7
A Bennington Christmas Carol
Monument Arts Center
“A Bennington Christmas Carol” returns for its 2025 run, a brand-new musical set in 1926 Bennington, retelling Dickens’ classic with local history, family names, and a full original score.
With beloved MAC Center performers, lively choreography, and a heartfelt story of redemption, this show is a highlight of the holiday season.
Additional performances: Dec 11–14 & Dec 18–21.
Friday–Saturday, December 5–6
Second Congregational Church – Snowball Bazaar
Kick off the holidays by supporting a community tradition. Shop the famous greens, Serendipity tag sale, bake sale, Treasure Chest, pet section, and enjoy the Snowball Café.
9:30 AM – 3:00 PM
December 6 Events
Family Day at Bennington Museum
A special $5 admission for everyone supports the Museum’s year-end programming.
Kids 17 and under get in free with a donation to Bennington County Multicultural Community Center.
Activities include:
• Children’s Shopping Boutique
• Bake sale
• Crafts (10 AM – 2 PM)
• Classroom Creations
• Santa & Mrs. Claus (10 AM – 12 PM)
The Turkey Is Fine, Staged Reading
Bennington Theater | 6 PM
A fast, fearless one-hour farce about family, chaos, and holiday dinner gone wrong.
Admission is free; donations encouraged.
Celtic Christmas – The SKY Family
North Bennington Baptist Church | 6 PM
A lively holiday performance featuring Celtic fiddle, humor, and heartfelt Christmas music. No tickets required; a love offering will be taken.
Vermont Paws & Boots, Santa Shoot
A beloved annual fundraiser | 10-4 PM
Bring the whole family, two-legged and four-legged, for photos with Santa, intuitive tarot readings, community fun, and food/drinks available from Pangaea Café.
Shires Holiday Inn Tours – Day 1
Seventeen inns, B&Bs, and lodging properties open their doors for festive decorations, treats, and holiday cheer.
11 AM – 3 PM
Proceeds benefit regional food shelves and Meals on Wheels.
More details.
Sunday, December 7
Park-McCullough House — Community Tree Lighting
Join neighbors and friends for a classic holiday celebration on the historic grounds.
Caroling, wagon rides, a hot cocoa bar, cookie exchange, and more.
FREE event. Sponsored by The Bank of Bennington.
Brunch With Santa at Mount Anthony Country Club
Celebrate the season with Santa and Mrs. Claus during a festive holiday brunch from 11 a.m. to 2 p.m. Families are invited to bring letters for Santa and a camera for photos.
Adults $36.95, kids 10 and under $19.95, and children 3 and under eat free. Reservations recommended at 802-442-2617.
Saturday, December 13 Events
Bennington Museum Gala, Art Deco Soirée
A glamorous evening of hot jazz, decadent dining, smooth cocktails, and a spirited silent auction.
Food by Pangaea; music by Silverback Swing.
Dress code: black, gold, pearls, feathers, fringe, the bee’s knees for this roaring soirée.
The Pownal Express
A magical spin on the Polar Express hosted by the Pownal PTG.
Enjoy reindeer games, cookies and cocoa with Santa, fireside movie time, Frosty’s snowball pit, an affordable gift shop, s’mores, dinner at the Polar Bear Café, and a town-light tour aboard the “train.”
Reservations required by Dec 3.
Gym admission is free; all riders need tickets.
Shires Holiday Inn Tours – Day 2
The second opportunity to explore festively decorated inns throughout The Shires.
11 AM – 3 PM
Thursday, December 18
A Holiday Evening with Beard & Glasses
Enjoy dinner and a show with this beloved local band performing holiday favorites at Pangaea Café.
$10 per person; all proceeds go directly to the musicians.
Saturday, December 20
A Cozy Christmas Cabaret, Bennington Theater
Doors 6 PM | Cabaret 7 PM
Featuring Amy Gaither, Matt Edwards, and special guests for an intimate evening of holiday classics, seasonal stories, and festive cheer.
All proceeds support Bennington Theater’s 2026 Season.
Tickets available at BenningtonTheater.org.
Wednesday, December 31
Noon Year’s Eve, Bennington Museum
For families who can’t stay up until midnight!
Join the Museum for music, party hats, noisemakers, sparkling grape juice, and a countdown to NOON.
11:15 AM – 12:15 PM
$5/child; adults free.
Friday, January 9
New Year’s Insights
Ring in 2026 with intuitive tarot readings from Zoë Thomas of Sacred Space Holistic Wellness and other mystics. Enjoy vision-board making, community time, and food/drinks available for purchase from Pangaea Café.
Planning for Christmas Eve or New Year’s?
If you’re deciding where to celebrate or looking for what’s open, don’t forget to follow @VermontBeginsHere on Instagram and Facebook.
Some notable local favorites for holiday dining and celebrations include:
• 421 Craft Bar & Kitchen
• Union South (entertainment room with pool)
• Harvest Brewing (karaoke & darts)
• Miller’s Toll
• Kelli’s Tavern
• Pangaea in North Bennington
• Mount Anthony Country Club
Start planning your trip today:
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