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Ottauquechee river in winter

From The Blog Weekend Fun: Celebrate the season with a winter solstice party, holiday workshops & markets, winter carols, & more

Tis the season for fun!

12/19/19-12/22/19: Have a happy ho-ho-holiday season with these local adventures that'll bring joy to everyone in your crew, young and old...

A Beautiful Day in the Neighborhood movie
A scene from the movie, A Beautiful Day in the Neighborhood


December 20-22 & beyond: Spend some time with Mr. Rogers during a showing of the uplifting film, A Beautiful Day in the Neighborhood, playing at Pentangle Arts’ Woodstock Town Hall Theatre.

December 21-22: Celebrate the holidays with a historic nod during activities like ornament painting and candle dipping as part of Christmas at the Farm at Billings Farm & Museum.


9 AM – 12 PM: Want to deck your Christmas tree with something made with heart by your own two hands? You can carve a traditional tree-topper with instruction from Lisa Kaija during the Wooden Star Carving workshop at Artistree. $25 per person, click here for more information.

11 AM & 3 PM: Two tastings in one day at one location: sample Cobb Hill Cheese (11 AM) and Vermont Amber Toffee (3PM), both at the Woodstock Farmers' Market.


1 – 2 PM: Want to join in on a Yankee Swap of gently used, wrapped gifts at the Thompson Senior Center? The more the merrier! See link for details.

3 – 7 PM: Give yourself the gift of attending a Holiday Open House at 37 Central Clothiers featuring giveaways, prizes, and 25% off store-wide where you can shop till you drop for fashionable finds.

Then, you have two more chances for hands-on holiday workshops at Artistree from 3:30 – 5:30 PM:

4 – 7 PM: Have some last-minute holiday shopping to attend to? You’re in luck! An evening of giveaways, light refreshments, samples, sales, and great conversation awaits during Customer Appreciation Nights at Clover Gift Shop, Phlox, and RT Home.

4 – 8 PM: Or, head to Barnard for dinner and a Pop-up Holiday Market featuring locally made goods from Caledonia Spirits, Janet Zug Glass Studios, Luce Farm, and more at the Barnard Inn Restaurant & Max’s Tavern.

wassail weekend dining
Ansel Dicky
Family and friends, let us do the cooking

5:30 – 7 PM: Sustainable Woodstock volunteers, it’s time to celebrate you! During this round of Green Drinks at Worthy Kitchen, all are welcome to raise a glass to the hard work of those who donated their time to this volunteer-driven organization.

Or, also from 5:30 – 7 PM, help the First Congregational Church celebrate a new tradition with their first annual Christmas Pageant!

6:30 PM: You can mix and mingle with neighbors and new friends over holiday treats made by you during an evening at Artistree! For just $5 per person, you’ll whip up distinctive edible gifts with instruction from chef Holly Pierce.

7 – 9 PM: Then, stick around at Artistree for their free Open Mic Night, where you can join the band and jam or take to the audience to enjoy the show.

Woodstock Farmers Market Indoors
Katie Berdan


12 – 3 PM: While you shop, you can explore the variety of hemp-infused products from Luce Farms during their demo at the Woodstock Farmers’ Market.

7 – 8:30 PM: Local choruses and musicians come together for the candle-lit ceremony, Winter Carols, presented by BarnArts at The First Universalist Church and Society of Barnard – where even the audience is invited to sing along. Free for all to attend.


10 – 11 AM: When Santa, pajamas, and pancakes come together, everyone wins! So don’t miss out on the Pajama Pancake Breakfast featuring special guest Old Saint Nick at the Barnard General Store! And be sure to have your cameras ready.

1 – 3 PM: Make and take your own body scrub, tea, and facial mask during Picked Herbals' Holiday Gift Making Herbal Workshop at Strong House Spa and Muscular Therapy Clinic. See link for pricing and reservations.

2 – 5 PM: Then, it’s party time! Celebrate the snowy season during a rocking Winter Solstice Party complete with fat biking, local brews, food, and live music at Suicide Six.

Skiing at Suicide Six Ski Area
Chip Allen
Learn to Ski & Ride at Saskadena Six Ski Area


4 PM: It's time for the South Woodstock Holiday Pageant! Watch as locals perform at the South Woodstock Community Church then follow the crowd to a community potluck at the South Woodstock Firehouse. Sign up for your potluck items at the South Woodstock Country Store or via an e-mail to

4:30 – 8:30 PM: All you need to bring for a Chanukah Celebration with Congregation Shir Shalom is a potluck dish perfect for sharing and yourselves, of course – because you don’t want to miss this evening of dreidel games, a latke contest, and candle-lighting.