What To Do in Woodstock, VT During the Holidays

By Kelley Boymer
30 Nov 2022
Woodstock inn snow - Woodstock Travel Guide

Woodstock is such a magical winter wonderland– especially during the holiday season. The village is decked out in twinkling lights, garland and the star on 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 truly 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
Grab drinks and light bites at au comptoir, Woodstock’s quaint village cocktail bar

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, 37th Central Clothiers, Red Wagon Toy Company, Unicorn, Sudie’s, Echo Market 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.

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.

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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, Blue Horse Inn, The Woodstocker B&B, Jackson House Inn or The Village Inn of Woodstock.

Visit Sugarbush Farm

Sugarbush Farm is a 3rd generational 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

Wassail Parade

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 horse and carriage holiday parade begins at 2pm on Saturday, December 10th 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 more Wassail Weekend events see here.

Christmas At The Farm

Running the whole month of December (every weekend and December 16th-January 1st, excluding December 24th and 25th), 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 24th, Thursday-Sunday and select dates during the holiday weeks from 5-7pm 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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Cookies With Santa

Don’t miss your chance to meet Santa and tell him what’s on your list this year! Head to the Town Hall Theatre on Sunday, December 11th from 12:30-1:30pm for Cookies With Santa. Enjoy cookies and other holiday treats and snap a picture of your little one on Santa’s lap!

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A Christmas Carol at Northern Stage

Located just 20 minutes outside of the Woodstock Village is a wonderful local theater called Northern Stage. This year’s holiday show is the classic, A Christmas Carol. Grab tickets now for showings between November 21st-December 31st.

A Cozy Christmas Cabaret: Holiday Songs & Stories

Head to the Little Theater in downtown Woodstock on Saturday, December 16th from 8-10 PM with local musician, Ben Kogan. A Cozy Christmas Cabaret is a great way to embrace the holiday season!

What are your favorite annual holiday events in Woodstock, VT? Let us know in the comments below.

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