What To Do in Woodstock, VT During the Holidays

Woodstock is a magical winter wonderland– especially during the holiday season. The village is decked out in twinkling lights, garland and the star at the top of Mount Tom twinkles from above the middle covered bridge. The Woodstock Inn (get 10% off your stay here) hangs colorfully lit stars from the trees in their front courtyard that hang like floating magical globes. The Village Green trees glow with sparkling white lights and you can feel the magic in the air.

The weather in Woodstock is chilly in December, usually in the 30s and 40s and oftentimes white, glistening snow blankets the ground. This cooler weather makes for the perfect opportunity to bundle up in your favorite festive winter coats, hats and mittens and snuggle up in cozy blankets around the fireside. You can truly feel the warmth, love and festiveness of the season in the air in Woodstock. Woodstock is one of the most beautiful small towns to visit during the holiday season. It turns into a a picture-perfect Christmas town with an old-fashioned holiday charm each holiday season. There are so many things to see and do in Woodstock, VT during the holiday season. If you are planning on visiting Woodstock this holiday season we have you covered. Here are some fun things to do in Woodstock, VT during the holidays.

Also check out the comprehensive Woodstock Guide here for all your trip planning needs. You can find more Vermont travel content here.

Is Woodstock, VT Worth Visiting During The Holidays?

Woodstock is most certainly worth visiting during the holidays, because it is everything you could possibly dream of when it comes to holiday cheer. This small New England town is incredibly charming and truly captures the essence of a magical winter wonderland, like a Norman Rockwell painting. There is something for everyone in Woodstock from snowshoeing and hiking amongst the wintery beauty to holiday shopping, dining in cozy settings and enjoying festive entertainment and events. Check out where to eat in Woodstock, VT here.

What To Do in Woodstock, VT During the Holidays

Visit for Wassail Weekend

If you are trying to catch Woodstock in its prime this holiday season, you can’t miss Wassail Weekend. This weekend is full of holiday magic and cheer with the Wassail Parade– a horse parade around the village green, sleigh rides, holiday house tours and a holiday crafts fair. There is so much to see and do during this festive weekend in Woodstock. Check out the Wassail Weekend line-up of events here.

Visit Simon Pearce

Simon Pearce in Quechee, Vermont is a wonderful place to visit if you are in Woodstock. Just a short 15 minute drive outside of Woodstock, Quechee is another small Vermont town. Simon Pearce is a glass blowing factory with a rich history, located in a beautiful mill overlooking the Quechee Covered Bridge and falls. Here you can dine in the restaurant or bar, shop for gifts in their shop or see the glass blowing up close in the workshop downstairs. Be sure to make reservations for the restaurant in advance as they book up quickly.

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Shop In The Woodstock Village

There are so many lovely shops to peruse along Main Street and Elm Streets in the Woodstock Village. Whether you are just window shopping or trying to check a few items off your Christmas list, you will enjoy the beautifully decorated window displays, twinkling lights along the streets and the stores full of local artisanal treasures, Vermont goods and more! Some of our favorites include: F.H. Gillingham & Sons, Clover Gift Shop, Woody’s, Yankee Bookshop, Elevation, Echo Market, Mahshu Vintage and RT Home.

Dine in the Woodstock Village

Amongst it’s wonderful shops are delicious places to dine in Woodstock. Try Mon Vert for an excellent coffee, breakfast or lunch, The Village Butcher for sandwiches, salads, meats and local products, Sante for small bites and entrees for lunch or dinner and Au Comptoir our quaint village cocktail bar. Au Comptoir is especially festive and cozy during the holiday season. Don’t miss fresh donuts and pastries from Farmer and the Bell. One of my favorite spots to bring guests when they’re visiting is Ransom Tavern at the Kedron Valley Inn. Such a cozy atmosphere in the winter months.

Visit Covered Bridges

What better way to capture your holiday in Woodstock than underneath a charming covered bridge? Even better if there is a dusting of snow to top it off. Try the Middle Covered Bridge across from the village green in Woodstock, the Taftsville Covered Bridge just a 5 minute drive out of town or the Quechee Covered Bridge. While in Quechee be sure to check out the famous Quechee Gorge.

Stay at The Woodstock Inn & Resort

The Woodstock Inn & Resort is located right in the center of the Woodstock village across from the town green. This beautiful resort is so festive and bustling during the holiday season. It is decked to the nines with gingerbread houses, lights, ribbons and gorgeous “floating” stars amongst in the courtyard in front of the inn. Click here for 10% off your stay (some blackout dates apply). Make sure you make an appointment at their fantastic Spa. The Tata Harper facial is my favorite treatment.

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Stay At A Charming B&B

If you are looking for more of the quaint small town experience, stay in one of Woodstock’s charming Bed & Breakfasts. There are so many lovely options to choose from with cozy fireplaces, whirlpools, luxurious robes, local goodies and more. Try The Vesper, The Woodstocker B&B, Jackson House Inn or The Village Inn of Woodstock.

Visit Sugarbush Farm

Sugarbush Farm is a 3rd generation family farm that makes their own cheese, maple syrup, jams, mustard, spreads and meats. Visit the farm for a tour of the sugarhouse and to learn how maple syrup is made. Browse their gift shop for yummy goodies and gifts. Admission is free and they are open daily 9am-5pm.

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Visit Billings Farm & Museum

During the month of December Billings Farm and Museum features, Christmas At The Farm. Experience a Victorian Christmas with olden day decor, a gingerbread house contest, candle making and more. Not to mention, their gift shop is an excellent place to shop for holiday gifts.

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Ski or Snowboard at Saskadena Six

Conveniently located in Pomfret just 10 minutes from the village of Woodstock, Saskadena Six is a family friendly mountain that also happens to be one of North America’s oldest ski resorts. With a newly installed magic carpet for beginners and wonderful instructors with private lessons and ski school, it’s a great place to learn to snowboard or ski. Have lunch by the fire after a morning on the slopes. Opening day is usually mid-December.

Woodstock, VT Holiday Events

Zack’s Place Turkey Trot

If you happen to be in Woodstock during Thanksgiving you can’t miss Zack’s Place Turkey Trot, an event the entire community comes out to participate. Participants can run or walk, and it’s a great fundraiser for Zack’s Place which is a vital place in our community dedicated to providing a space space for individuals with special needs to explore art, cultural, fitness, and educational programs while developing friendships.

Woodstock Wassail Weekend

Woodstock Wassail Weekened and the Wassail Parade is one of the most highly anticipated events of the season in Woodstock, Vermont. Many annual events throughout town are planned around this festive parade. The weekend (December 13-15) will kick off with a parade through town from East End Park to the Village Green on Friday evening. On Saturday, the horse and carriage holiday parade begins at 2pm, and proceeds around the village green. The horses, equestrians and carriages are decked out in both traditional and festive costume from head to toe. The event culminates with a tree lighting, caroling and lighting of luminaries in the early evening. For the full Woodstock Wassail Weekend schedule of events see here.

Christmas At The Farm

Running the whole month of December (every weekend in December and daily from December 21-January 1, excluding December 24-25), visit Billings Farm and Museum for Christmas At The Farm. Experience a Victorian Christmas in the beautifully decorated farmhouse parlor, festive decor throughout the farm, enjoy hot cocoa and s’mores fireside, meet the animals in the barn and enjoy fun festive activities like candle making and a gingerbread house contest. Need to check a few gifts off your Christmas shopping list? Visit the Billings Farm Gift Shop for a wonderful selection of local goodies. Billings Farm is the perfect outing for the whole family to enjoy!

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A Forest of Lights at VINS

Head to VINS in Quechee, VT (15 minute drive from Woodstock) for A Forest of Lights. Beginning on November 22-January 4, from 4:30-7pm throughout the holiday season, enjoy a beautiful display of lights amongst the canopy walk at VINS. Be sure to buy tickets ahead of time as they sell out fast!

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Holiday Cabaret & Winter Carols At BarnArts

Head to Artistree for a festive, musical performance of Holiday Cabaret on December 10th at 7:30pm. Check availability and purchase tickets here. If you’re in town you won’t want to miss the beautiful sounds of Winter Carols to ring in the holiday season on Friday, December 15th at 7pm.

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Peter and Wendy at Northern Stage

Located just 20 minutes outside of the Woodstock Village is a wonderful renowned theater called Northern Stage. This year’s holiday show is Peter and Wendy. Grab tickets now for showings between December 4-January 1.