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Christmas tree and presents

From The Blog Weekend Fun: Holly jolly happenings around town

Twas the weekend before Christmas when all through the town, there was much jolly activity to be found! Read on to learn more...


Check out our village shop guide to alleviate those last-minute holiday shopping woes!

December 20-22: Admire an exhibit of Small Works during the closing weekend of Artistree’s Holiday Show! Here, you’ll find a wall of 50 panels measuring 50 square inches each – each one a great last-minute holiday gift!

December 20-23: Or if you’re in WRJ, head to the AVA Gallery for their take on a Holiday Exhibition & Sale, complete with paintings, handmade ornaments, pottery, jewelry, and more.

December 20-23: The 46th Annual Christmas Show & Sale is coming to a close! This is your last weekend to visit the Upper Valley Plaza in Lebanon for handmade wares and vendor demos.

December 20-23 & beyond: You can still catch a performance of the Tony Award-winning musical, Matilda, in WRJ – but hurry up and reserve your seat – many showings are sold out!

December 21-23: Take a seat and enjoy the show, because Fantastic Beasts and the Crimes of Grindelwald is playing at Pentangle Arts’ Town Hall Theatre!

December 22-24: Sleigh all day at Billings Farm & Museum! During the farm’s Christmas celebrations, you’ll enjoy this holiday the old-fashioned way, with festive decorations, farm exhibits, historic ornament making, and sleight/wagon rides (conditions permitting).

horse-drawn sleigh ride at Billings Farm
Billings Farm staff photo
Sleigh rides around the farm.


9:30 AM: Warm up your instrument for a Morning Jam session at Artistree, where those of all musical abilities are welcome to participate or pull up a chair and listen.

4 – 6 PM: Get some cookie decorating under your belt – then in your stomach! – at the Christmas Cookie Party at Mon Vert Café. $10 per child (or child at heart) includes 3 cookies, a hot cocoa, and unlimited decorations.

6 – 9 PM: Join friends and allies at another night OUT in the Valley, a LGBTQ happy hour at the Skinny Pancake in Hanover.

For a melodic holiday experience:


11 AM – 12 PM: Cozy up for a round of Winter Storytime: Tales for the Season at VINS! During this session of the read-aloud story series, you’ll be regaled with the story, Extra Yarn, written by Mac Barnett, followed by a craft and live animal encounter.

3 – 6 PM: Then grab a sled, zoom down the slopes of Suicide Six, and repeat till you’re ready to hit the base lodge for their Yule Log Celebration full of toasty s’mores, eggnog, and a festive holiday film! Free for all, but supplies are limited. UPDATE: THIS EVENT IS CANCELED DUE TO WEATHER.

6 – 8 PM: Later, get your charcuterie skills up-to-snuff right in time for the holidays with Vermont Farmstead Cheese Co.’s Cheese Board Class at their market in Windsor! Reservations required.

7 – 9 PM: Then, send the kids out for some splash-tastic fun during Splash Night at the Upper Valley Aquatic Center in WRJ! $5 at the door (for grades 4-8 ONLY) includes music, food, games, and pool access.

Fire in fireplace


7 – 10 AM: Get some facetime with St. Nick in early during a Breakfast with Santa at the Bridgewater Diner – served with a side of delicious food and family-friendly crafts.

Two book-signing opportunities are headed your way:

3 – 8 PM: Try before you buy! At the Brownsville Butcher & Pantry, you can sample what you might serve at holiday celebrations during the Wine Tasting with Artisanal Cellars.

3:30 – 5 PM: Stick around after a day of downhill at Suicide Six for Kids' Apres Ski in the lodge, featuring music by Jim Yeager and sledding for the kids!

5 – 8 PM: “Tis the Season” for A Holiday Evening at Artistree! Join in on this closing reception for the Small Works show for art, caroling, and a medley of performances at the Grange Theatre.

5:40 – 7 PM: Or hit the ice at the Union Arena in Woodstock and share the limelight with Santa himself as he zips around on his skates. Available to the public.

From 6 to 10 PM, get festive at an Ugly Sweater Party hosted by Liquid Art Coffeehouse in Killington.

Then, party the night away at one of two events beginning at 9 PM:

Learn to ski at Saskadena Six Ski Area
Chip Allen


10 AM – 2 PM: Chow down in (questionable) style at the Ugly Sweater B(ee)runch at Trail Break Taps + Tacos in WRJ!

3 – 4:45 PM: Laugh the evening away during a showing of the film, Christmas with the Kranks, playing at Pentangle Arts' Woodstock Town Hall Theatre.