With December right around the corner, we wanted to share some fun and family-friendly holiday events happening right here in Bennington. If you’ve yet to find yourself in the holiday spirit, now is the time to get out and enjoy all that Bennington has to offer, from holiday tours and a tree lighting to brunch with our favorite jolly old elf. Here’s what’s going on in Bennington, Vermont for the holidays.

December 4: Home for the Holidays Celebration

A poster featuring the Christmas tree lighting in Bennington, Vermont.
Come Home for the Holidays!

5:30 – 7:30 pm

Kick off a month of holiday celebrations in Bennington with this fun evening celebration at the Vermont Veteran’s Home and the Shires Area Chamber of Commerce. Start the evening off with a downtown stroll and a lantern walk courtesy of the Bennington Area Makerspace. Then, head to the Vermont Veteran’s Home for the community tree lighting ceremony featuring the Mount Anthony Union High school choir, keynote dignitaries, and a special visit from Santa Claus. After the tree lighting, take a candlelit walk through the deer park on your way to the Chamber of Commerce to decorate your own cookies, warm up around the fire pit, and enjoy refreshments. 

The Hometown Holiday Celebration is a fabulous way to kick-off December with the Bennington community. Visit the Shires Area Chamber of Commerce to learn more. 

December 7 and 14: Holiday Historic Inn Tours

The Four Chimneys Inn in Bennington, Vermont all decked out for the holidays.
The Four Chimneys Inn will be all decked out for the holidays! Photo credit: The Four Chimneys Inn

12 – 4 pm

Have you ever wondered how your favorite historic inns decorate for the holidays? Find out with a walk through history at some of Southern Vermont’s most famous inns. The Holiday Historic Inn Tours will feature 15 inns in Southwestern Vermont who will open their doors on two Saturdays in December. 

Our own Four Chimneys Inn will be representing Bennington. “This event is one of my favorite all year,” says Lynn Green, owner of The Four Chimneys Inn in Old Bennington.  “ It’s the perfect excuse to come do your holiday shopping in Vermont while also seeing the inside of 15 beautiful inns all decked out for the holidays .”

Each location plays host in a unique way, making for a cozy and fun Saturday afternoon in some of Vermont’s most beautiful spots. Tickets are $15 per person or $25 per couple, with proceeds supporting local food cupboards.  

Participating inns include: 

  • The Four Chimneys Inn: Bennington 
  • Seesaws Lodge: East Peru
  • Wilson House: East Dorset
  • Inn at Manchester: Manchester  ***7th only
  • The Reluctant Panther: Manchester
  • The Taconic Hotel: Manchester
  • The Equinox Hotel: Manchester
  • Wilburton Inn: Manchester 
  • The Inn at Ormsby Hill: Manchester Center
  • The Ira Allen House: Sunderland
  • Hill Farm Inn: Sunderland ***7th only
  • The Arlington Inn: Arlington
  • West Mountain Inn: Arlington
  • Rockwell Studio and Inn on Covered Bridge Green: Arlington

December 7: The Festival: A Snowy Evening Family Day at the Bennington Museum

Santa and Mrs. Claus hand out candy to a small child at the Bennington Museum in Bennington, Vermont.
Visiting with Mr. and Mrs. Claus at the Bennington Museum. Photo credit: The Bennington Museum

10 am – 5 pm

This wonderful, family-friendly event features kids’ crafts, a children’s shopping boutique with free gift wrapping, visits with Santa, and special deals at the Bennington Museum store. $3 admission for everyone and children who bring an item to donate to the Bennington County Coalition for the Homeless are admitted free.

This is the perfect time to catch those exhibits you’ve been waiting to see, including The Festival: A Snowy Evening, featuring works by thirty-one regional artists who have responded to the words of Robert Frost. This special exhibit will be on display in the Parmelee and Limric Galleries until December 30, and artwork will be available in a closed-bid auction through December 22. 

Looking to celebrate the holidays a little more lavishly? You won’t want to miss the Festival Gala: A Snowy Evening on December 14 at 7 pm. Not only is this the Bennington Museum’s largest fundraiser of the year, but it also features the incomparable Hot Club of Saratoga, special drinks courtesy of Madison Brewing Company, seasonal fare and appetizers, and a silent auction with over 45 unique items. 

December 7: An Old Fashioned Christmas at Park McCullough House

2 – 6 pm

An Old-Fashioned Christmas at Park McCullough is a free event at one of New England’s finest and best-preserved Victorian mansions. The Playhouse and the main floor of the house will be decked out for the holidays. Santa will be on hand near the grand fireplace to welcome children, and visitors can enjoy tractor rides around the grounds as well as Christmas caroling. Kids are welcome to enjoy a cozy storytime with Mrs. Claus and ornament crafting in the Carriage Barn. A tree lighting ceremony will be held on the veranda at 4 pm, so be sure to dress for the weather. 

This historic home is a treasure of North Bennington, and a visit for an Old Fashioned Christmas is sure to put you in the holiday spirit.

December 8: Brunch with Santa at Mt. Anthony Country Club

A flyer advertising brunch with Santa at Mt. Anthony Country Club in Bennington.

11 am – 2:30 pm

Brunch with Santa is a Bennington tradition featuring delicious breakfast and lunch fare, scrumptious deserts with both Santa and Mrs. Claus. Families are invited to read letters with Santa, pose for pictures, and bring reindeer food home to put out on Christmas Eve.

According to Jen McKenna, who has been attending for many years, “Brunch with Santa has always been a magical experience for our family. The look on the girl’s faces when they see Santa and Mrs. Claus is priceless.   And the festive decorations and excellent food tie a big red bow on this lovely tradition.”

What a special way to welcome the Christmas season. Bring your camera, letters to Santa and your appetite!

Visiting Bennington, Vermont for a holiday event? Be sure to check out our full listings for unique shopping and dining ideas.