The Sandisfield Times
The Holidays in Sandisfield
A Lineup of Good Cheer
by Emily Ruocco
Published December 1, 2025

image of Santa.
Photo: Sandisfield Times.

The holidays are here, and our Town is glowing with the warmth of the season. Whether you love baking cookies, shopping for handmade gifts, singing carols or just listening, or simply spending time with friends and family, there's something wonderful waiting for everyone this December.

Browse the bounty of local farms and artisans. You'll find fresh greens, root vegetables, meats, cheeses, baked goods, jams, and maple syrup. There's live music and plenty of holiday cheer while you shop for locally made gifts and treats.

December in Sandisfield is all about coming together and celebrating the warmth of community.

Wishing everyone peace, joy, and plenty of holiday sparkle,

Happy Holidays from The Sandisfield Times!

advertising for Domaney's liquor store.


In Sandisfield

Annual Holiday Fair

Saturday, December 6, 10:00 a.m. to 2:00 p.m. Fire Station #2, Route 57.

Start your holiday season with one of Sandisfield's most beloved traditions. The Holiday Fair is filled with handmade crafts, delicious baked goods, raffles, and more than forty local vendors. Santa will arrive around 11 a.m. to visit children and spread cheer. This event benefits the Sandisfield Scholarship Fund and is co-sponsored by the Sandisfield Historical Society and the Recreation Committee. Email: sandisfieldevents@recreationcommittee.info


Unveiling: A Show of Portraits [Final Day]

Sunday, December 7, 11:00 a.m. to 3:00 p.m. Sandisfield Arts Center

Stop by the Sandisfield Arts Center for the closing day of this wonderful portrait exhibit featuring the work of talented local artists. A lovely Sunday afternoon surrounded by creativity, conversation, and community. Contact: Sandisfield Arts Center sandisfieldartscenter.org.


Seniors Invited to Holiday Luncheon

Thursday, December 11, 12 noon. Knox Trail Inn, Otis.

The COA is inviting Seniors to a Holiday Luncheon. The cost is $10 per person.


21st Annual Cookie Swap at the New Boston Inn

Sunday, December 14, 1:00 p.m. Upstairs Ballroom, New Boston Inn.

Calling all cookie lovers! The New Boston Inn will host its 21st Annual Cookie Swap in the beautiful upstairs ballroom. Bring 36 homemade cookies on a platter and a container to take home your swapped treats. Santa will also make an appearance! It's a fun and festive afternoon filled with sweetness, laughter, and good company. Please RSVP to (413) 258-4477. Contact: New Boston Inn


Evening Advent Bible Study and Fellowship

Sunday, December 14, 5:00 to 7:00 p.m. New Boston Congregational Church.

Take a break from the holiday rush for an evening of reflection and fellowship. Enjoy a short Advent service followed by homemade soup, sandwiches, and Christmas cookies. Everyone is welcome to come and share the peace & joy of the season. Contact: New Boston Congregational Church newbostoncongregationalchurch.org.


Community Christmas Sing-Along

Sunday, December 21, 5:30 to 7:00 p.m. New Boston Congregational Church.

Join friends and neighbors for an evening of joyful singing and holiday spirit. Gather around for favorite carols and Christmas songs that fill the church with warmth and laughter. The event is free and open to everyone, with donations appreciated to support the church's community programs. Contact: New Boston Congregational Church newbostoncongregationalchurch.org.


Nearby Festivities

Holiday Carriage Rides and Craft Fair in Winsted

Saturday, December 6, 11:00 a.m. to 1:00 p.m. Corner of Main and Elm Streets, Downtown Winsted/Whiting Mills

Bundle up for a magical morning in downtown Winsted. Enjoy horse-drawn carriage rides by Utopia Percherons of Goshen, hot cocoa served by Boy Scout Troop 1027, storytelling, and caroling by The Gilbert School singers. The Winsted Fire Department will be serving s'mores, and Whiting Mills will host its Holiday Makers Shoppes with open studios and unique local crafts. Contact: Friends of Main Street fomswinsted.org.


Holiday Marketplace at Berkshire Botanical Garden

Friday, December 5 through Sunday, December 7 Berkshire Botanical Garden, Stockbridge This three-day holiday market is a perfect outing for the whole family. Explore artisan craft vendors, children's activities, and beautiful holiday greenery in a festive garden setting. Contact: Berkshire Botanical Garden berkshirebotanical.org.


Holiday Fair at New Marlborough Center School

Saturday, December 6, 11:00 a.m. to 2:00 p.m. 44 Hartsville-New Marlborough Road

Enjoy food, live music, crafts, and baked goods. Don't miss the community auction, with online bidding opening December 1. Contact: New Marlborough Center School (see Facebook for updates)


Lenox Winter Market, Shop, Sip, and Savor

Saturday, December 6, 12:00 to 4:00 p.m. Downtown Lenox

Take a stroll through the charming streets of Lenox while browsing local shops, sampling holiday treats, and enjoying live music and art. It's the perfect way to spend a December afternoon. Contact: Lenox Chamber of Commerce (lenox.org) Christmas for Kids Fundraiser and Spindle Music Bingo

Sunday, December 14, 2:00 to 6:00 p.m. Knox Trail Inn, 1898 East Otis Road, East Otis


Join the Knox Trail Inn

Have fun while giving back! Join the Knox Trail Inn and AMVETS Post 77 for an afternoon of Spindle Music Bingo hosted by DJ Pup Daddy. Your $20 donation for four bingo cards goes toward helping families in need this holiday season. There will be a dance party, prizes, and a Best Christmas Outfit contest. Contact: Knox Trail Inn (413) 269-4400


Berkshire-Grown Winter Farmers Market

Saturday, December 20, 10:00 a.m. to 1:00 p.m. Housatonic Community Center, 1064 Main Street, Housatonic

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Published December 1, 2025