Christmas in Woodstock VT 🎄 12 Festive Things to Do in 2023

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One of my most favorite places to visit in all of New England, Woodstock, Vermont 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 Christmastime in Vermont is always lovely, but head to Woodstock VT for a healthy helping of small-town Christmas charm.

There are cozy places to stay, yummy places to eat, and all the wholesome 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 of my favorites!

Christmas in Woodstock VT

Wassail Weekend

Downtown decorated for Christmas in Woodstock VT
Editorial credit: James Kirkikis /; Christmas in Woodstock VT

The undisputed star of the holiday season in Woodstock is Wassail Weekend.

This wonderfully festive weekend event takes place the second weekend of December, recreating historic New England Christmas charm with events held at Billings Farm, the beautiful 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 music events that will keep you feeling that Woodstock Vermont Christmas spirit.

I don’t know about you, but for me, this is pure Christmas charm!

2023 Wassail Weekend Info

December 8 – 10, multiple events but highlights include: 

Bagpipe rock concert with Prydein, December 8, 7:30 pm – 9:30 pm

Holiday Ornament Making, December 9, 10 am – 12 pm

Drinks & S’mores + the Ten of NYC A Capella group, December 9, 11 am – 2 pm

Wassail Parade, December 9, 2 pm

Holiday Showcase at the Grange Theatre, December 9, 7 pm – 8:30 pm

The Yale Alley Cats on The Green, December 9, 7:30 pm – 9:30 pm

Have Breakfast at Mon Vert Cafe

The lovely Mon Vert Cafe is one of my favorite breakfast places in Woodstock VT. They’ve got a great food menu and their coffee is *Chef’s Kiss* good.

A plate of waffles with a maple latte at Mon Vert Cafe in Woodstock, Vermont

I LOVE their maple lattes, and I wholeheartedly recommend you order one to get your day off to a great start during your Christmas in Woodstock Vermont.

Check out Christmas at the Grange

Just 10 minutes up the road in South Pomfret is Holiday Showcase at the Grange, a can’t-miss live music spectacular featuring 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, not just one of the best restaurants in Woodstock.

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?

Click Here to Check Prices & Book!

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!

A two story historic brick building with the name F.H. Gillingham & Sons on the front.
Historic shops like F.H. Gillingham’s are one of the reasons Woodstock is such a charming small town!

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.

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. I love stopping by when we visit Woodstock!

Enjoy Cookies with Santa

Are you spending your Woodstock Christmas with kids? 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?? 

2023 Cookies with Santa Info

December 10, 12:30 pm – 1:30 pm, free with donations accepted!

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?

2023 Skate with Santa Info

December 10, 10:40 am – 12:10 pm

Have Your Christmas Feast at Woodstock Inn and Resort

Woodstock Inn decorated with christmas lights, garlands, and wreaths
Editorial credit: James Kirkikis /; Woodstock Inn and Resort is a beautiful place to stay in Woodstock at Christmastime!

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?

Click Here to Check Prices & Book!

2023 Christmas Dinner Buffet Info

December 25, 2023, served 12 pm – 7 pm in the Rockefeller Room, Reservations Required & open to guests only

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 Woodstock 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.

2023 Christmas at the Farm Info

December 16, 10 am – 4 pm

Snuggle Up in 506 on the River Inn

One of my favorite places to stay in Woodstock, 506 on the River Inn offers 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!)

Seriously, the indoor play room and the gorgeous lawn are fantastic for family travel.

You’ll also find an indoor pool and sauna if you’d like 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. 

Click Here to Check Prices & Book!

Want to read my full review of 506 on the River Inn? Click here!

Play in the Snow at the Woodstock Nordic Center

Child cross country skiing in wintry forest in Woodstock VT at Christmas
Christmastime in Woodstock Vermont is the perfect time for playing in the snow!

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 Woodstock VT 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 Saskadena 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 Woodstock VT at Christmas is so much fun.

Head up the Road to the VT Holiday Festival

Okay, so this one is technically in nearby Killington, but the Vermont Holiday Festival is well worth the short drive from Woodstock!

Throughout this holiday weekend event you’ll find plenty of local vendors, a festival of trees, caroling, and of course, Santa!

There’s even a Breakfast with Santa, so be sure to grab a ticket while supplies last if you’re traveling to Woodstock VT with kids.

2023 Vermont Holiday Festival Info

December 8 – 9 at the Grand Hotel Ballroom

2023 Christmas in Woodstock VT Wrap-Up

Woodstock is one of the most beautiful places in all of Vermont, and is one of the best places to go to enjoy winter fun.

Have fun making Merry Christmas memories during your Christmas in Woodstock.

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