10 Fun and Festive Things to Do for Christmas in Woodstock VT


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One of the most charming small towns in New England, Woodstock becomes even more charming during the holidays! Christmas in Woodstock VT offers a taste of that quintessential New England holiday flavor that is so often captured in Hallmark Christmas movies; truly, Woodstock VT looks like a Hallmark Christmas movie town come alive!

Choosing to spend Christmas in Vermont is always lovely, but head to Woodstock VT for a healthy helping of small-town Christmas charm. There are cute places to stay, wonderful places to eat, and all the wholesome New England Christmas activities you could hope for during a Christmas getaway in Vermont! 

There are so many ways to have a Merry Christmas in Woodstock VT, these are just a few!

Wassail Weekend

Downtown decorated for Christmas in Woodstock VT

Editorial credit: James Kirkikis / Shutterstock.com

The undisputed star of the holiday season in Woodstock is Wassail Weekend. This wonderfully festive weekend event typically occurs the second weekend of December, recreating historic New England Christmas charm with events held at Billings Farm (a must-visit spot on this essential New England bucket list!), the dairy farm and museum that introduces visitors to the Vermont dairy farm way of life, past and present. 

There are fire pits, hot chocolate, coffee, wassail punch, cider donuts, and horse-drawn wagon and sleigh rides. Wassail Weekend at Billings Farm is a sweet holiday tradition for locals and visitors alike, with the entire town in on the festivities! You’ll find carriage rides through town, Christmas movie nights with popcorn and sweet treats, historic decorated homes, and Christmas music events that will keep you feeling the Christmas spirit everywhere you turn!

Check out Christmas at the Grange

Just 10 minutes up the road in South Pomfret is Christmas at the Grange, a can’t-miss live music spectacular featuring holiday Broadway hits and beloved Christmas staples performed in the lovely Grange Theatre! The Grange also offers other great shows and events throughout the holiday season, so be sure to check out the event calendar to see what’s coming up while looking for things to do during your Woodstock Christmas.

Lunch at the Lincoln Inn & Restaurant at The Covered Bridge

Middle Covered Bridge with Christmas wreath in Woodstock VT

The award-winning Lincoln Inn & Restaurant has been lauded as one of the best restaurants in the country, and in addition to its Michelin Star trained chef’s expertly executed dishes, the ambiance of this comfy cozy inn restaurant is perfect for a holiday lunch or dinner during your Christmas vacation in Woodstock! Request a spot by the crackling fireplace for the ultimate experience of Christmas coziness while you dine. Plus, there are the quintessentially Vermont covered bridge views as you arrive to give you all those warm holiday feels… can it get much more “Christmas in a Hallmark Card” than that?

Visit F.H. Gillingham and Sons

For a unique holiday shopping experience at one of the neatest shops around, visit F.H. Gillingham and Sons, the general store that has been serving the Woodstock community since 1886! You’ll find Vermont food staples like locally-produced maple syrup, maple butter, cheeses, jams, jellies, and more to put under the tree for your favorite folks, or if you’re looking for a non-perishable gift, check out their comfy, cozy Christmas-in-Vermont suited clothing options that include fuzzy socks and warm, woolen robes that will keep you and yours warm all winter long!

A visit to F.H. Gillingham and Sons is a unique Woodstock VT experience to enjoy and cross off your Vermont bucket list; plus, F.H. Gillingham and Sons is the perfect spot for some extra festive Christmas selfies, too!

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Enjoy Cookies with Santa

Are you spending your Woodstock Christmas with little ones? If so, you’ve got to visit Woodstock’s historic Townhall Theatre for their Cookies with Santa event, a sweet, small town visit with Santa! Visits and photos with Santa take place on the stage and kiddos are given complimentary cookies, holiday lollipops, and juice boxes to enjoy during their visit. How adorable is that?? 

PS you can also catch the holiday favorite, A Christmas Carol, being performed here, too!

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Ice Skating at Union Arena

Lace up your favorite skates (or rent a pair there) so you can go ice skating at Woodstock’s Union Arena Ice Rink while festive Christmas music fills the air! Is there anything more magical than twirling around on the ice? In fact, Santa makes the occasional appearance during December, too, so you just might get to skate with Santa while you’re there, too! How’s that for a unique Christmas memory?

Have Your Christmas Feast at Woodstock Inn and Resort

Woodstock Inn decorated with christmas lights, garlands, and wreaths

Editorial credit: James Kirkikis / Shutterstock.com

If you’re planning on spending Christmas Day in Woodstock, there’s no better place to dine than this gorgeous inn’s spectacular Christmas Buffet! Open to guests of the inn only, you’ll have to stay at the inn for entrance, but seeing as Woodstock Inn and Resort is considered to be one of the most romantic getaway destinations in the state, it’s not too much of a chore, is it?

With a full-service spa and gourmet chef, who wouldn’t want to incorporate a stay at this luxurious Vermont inn into your Christmas holiday?

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Partake in Christmas at the Farm

That’s right, back to historic Billings Farm for Christmas at the Farm! In addition to participating in Wassail Weekend, Billings Farm and Museum also provide wholesomely festive Christmas fun for the rest of the season, too! You’ll find fun in the snow like snowshoeing and sleigh riding, and old-fashioned holiday activities like candle dipping and ornament making. 

Toast your own s’mores at the fire pit while warming up with a steaming hot cup of cider or coffee. Billings Farm and Museum is a marvelous sight with the Christmas lights and fresh garlands hung around for all to see! Don’t forget to visit the farm animals while you’re there.

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Snuggle Up in 506 on the River Inn

One of the best hotels in Vermont, 506 on the River Inn is one of Woodstock’s shining gems, with rooms and suites that go all-in on Vermont charm and hospitality with thoughtful touches and amenities for families like the kid’s room, game room, and outdoor fire pit (perfect for toasting marshmallows!) You’ll also find the indoor pool and sauna to be the perfect places to unwind and decompress during your Woodstock getaway, and when you’re hungry, the onsite bistro and bar have a wide range of scrumptious options to satisfy even the pickiest eaters. 506 on the River Inn is a perfect base for your Woodstock Christmas getaway.

Play in the Snow at the Woodstock Nordic Center

Child cross country skiing in wintry forest

The Woodstock Nordic Center is the place to go for fun in the snow during your Woodstock Christmas getaway! If you like a little active outdoor winter fun with your Christmas festivities, the Nordic Center at Woodstock Inn and Resort can help you with that with their rentals for snowshoeing, fat biking, and cross country skiing tours through their generous network of trails through Mt Peg and Mt Tom.

If you’d rather get a little height and speed, head the 10 minutes up the road to Suicide Six Ski Area to do some downhill skiing and snowboarding with 24 hills and slopes to play on! Playing in the snow is one of the reasons a winter vacation in Woodstock is so much fun.

Woodstock is one of the most beautiful places in all of Vermont, and there are so many fun things to do during your visit there! Woodstock is one of the best places to go to enjoy winter in Vermont; have fun making Merry Christmas memories during your Christmas in Woodstock.

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