Christmas in Woodstock, Vermont: Holiday Traditions, Cozy Dining, and Small-Town Charm
A Woodstock, Vermont, Christmas is built around the village itself. In 2026, Wassail Weekend runs December 11 to 13, with a horse-drawn parade around the Village Green, a yule log bonfire and carols as the Memory Tree is lit. On the edge of the village, Billings Farm & Museum decorates its 1890 farmhouse for a Victorian Christmas, and the shops around the Green are stocked with Vermont-made gifts.
On The River Inn sits beside the Ottauquechee River, minutes from Woodstock Village, so you can spend the day at the parade or the farm and come back to an indoor pool, a sauna and dinner at 506 Bistro & Bar. Here is how to plan a December visit, with event dates, places to shop and eat, and practical tips for getting around in winter.
TL;DR: Woodstock’s Christmas season at a glance
- Wassail Weekend 2026 runs Friday, December 11 to Sunday, December 13, with the Wassail Horse Parade on Saturday at 2pm.
- Billings Farm & Museum hosts its Winter Celebration on December 5 and 6, then daily from December 19, 2026 to January 3, 2027. It is closed December 24 and 25.
- The village center is compact, so the Green, the Middle Covered Bridge and the shops on Central and Elm Streets are easy to cover on foot in good winter boots.
- For Christmas gifts, F.H. Gillingham & Sons has traded on Elm Street since 1886, and Sugarbush Farm sells its own cheese and maple syrup year-round.
- 506 Bistro & Bar at On The River Inn currently serves dinner Thursday through Monday, 5pm to 9pm.
Why Woodstock Is One of Vermont’s Classic Christmas Towns
Woodstock is one of the Vermont Christmas towns people picture when they think of a New England holiday. The village is laid out around an oval Green, with historic homes, church steeples and independent shops within a few minutes’ walk of one another.
The Middle Covered Bridge is a good first stop. Built by Milton Graton in 1969, it carries Union Street across the Ottauquechee River into the heart of the village, and it is a natural place to start a winter walk. For more ideas beyond the holidays, see our guide to unique things to do in Woodstock, VT.
Wassail Weekend in Woodstock: December 11 to 13, 2026
Wassail Weekend is Woodstock’s signature holiday event, run by the Woodstock Chamber of Commerce with community partners and volunteers. Look for hot wassail punch at the Wassail Café on the Green.
The times below come from the 2026 schedule published by the Woodstock Chamber of Commerce. Check the official Wassail Weekend schedule before you travel, since details can change.
Friday, December 11
- Wassail Artisan Market on the Green, 1pm to 6pm.
- Horse and carriage rides in the village, 1pm to 3pm.
- Select village shops open until 7pm, with ticketed evening performances from 7pm.
Saturday, December 12: Parade Day
Saturday is the main day. The Wassail Horse Parade starts at 2pm, with horses, carriages and live music circling the Village Green twice. At 3pm, the Memory Tree is lit, the yule log bonfire is set alight and everyone gathers for a community carol sing, followed by the lighting of the luminaries on the Green at 4pm.
Parking in the village fills quickly on parade day. A shuttle runs from 9:30am to 5pm between Woodstock Union High School and River Street by the Middle Covered Bridge, with $5 parking that supports Woodstock Youth Hockey.
Sunday, December 13
Sunday has a slower pace, with carriage rides from 10am to 2pm, cookies and hot chocolate with Santa from 11am to 2pm, a morning open skate at Union Arena, and a Messiah sing at 4pm (reservations required).
Billings Farm & Museum also runs its own Wassail Weekend activities on all three days, 10am to 4pm, with orchard wassailing, candle dipping and hot spiced cider by outdoor fire pits.
A Victorian Christmas at Billings Farm & Museum
Billings Farm & Museum is a working dairy farm and museum on the edge of Woodstock Village. Its Winter Celebration on the Farm runs December 5 and 6, 2026, then daily from December 19, 2026 through January 3, 2027, from 10am to 4pm. The farm is closed December 24 and 25.
The 1890 Farm Manager’s House is decorated with 19th-century holiday trim. Recent Winter Celebrations have also included candle dipping, hot cocoa by the fire pits, time with the farm animals and Vermont-made gifts from the museum shop.
Horse-drawn sleigh or wagon rides run on select days, weather permitting, and private sleigh rides can be reserved separately. Traveling with children? Our guide to family vacations in Woodstock has more ideas for all ages.
Christmas Shopping in Woodstock Village
Woodstock’s shops are a big part of a Christmas visit, and most are within a short walk of the Green. During Wassail Weekend, the Artisan Market on the Green adds Vermont makers to the mix.
F.H. Gillingham & Sons
Open on Elm Street since 1886, F.H. Gillingham & Sons is a general store that works with local cheesemakers and farmers. Stop in for Vermont food gifts, stocking stuffers and everyday supplies.
Yankee Bookshop
Dating back to 1935, the Yankee Bookshop on Central Street is a good stop for a Vermont cookbook, a local history title or a book to read by the fire.
Sugarbush Farm
A short drive from the village, Sugarbush Farm is open daily, year-round, from 9am to 5pm. Sample more than a dozen of the farm’s cheeses, see how its maple syrup is made and take home a gift box for the holidays.
Woodstock Farmers’ Market
On West Woodstock Road, the same road as On The River Inn, Woodstock Farmers’ Market is a specialty grocery with a bakehouse for pies, cookies and desserts, along with Vermont cheeses, wine and local cider. It is open 8am to 7pm and closed on Mondays.
Cozy Dining in Woodstock Over the Holidays
Mon Vert Café
On Central Street, Mon Vert Café serves breakfast and lunch made with local and organic ingredients, along with homemade baked goods and Vermont Coffee Co. coffee. The kitchen closes at 3:30pm, and the café is closed on Thursdays.
506 Bistro & Bar
After a day at the parade or the farm, 506 Bistro & Bar at On The River Inn lets you settle in for dinner without heading back into the village. The menu changes with the seasons and leans on fresh, local ingredients, and the bar pours seasonal cocktails, Vermont craft beers such as Heady Topper and Citizen Cider, wines and mocktails.
Dinner is currently served Thursday through Monday, 5pm to 9pm, and you can reserve a table on OpenTable. Holiday hours can vary, so check ahead if you are planning dinner around Christmas.
Winter Activities Around Woodstock in December
Snow adds plenty to do between holiday plans. The carriage roads and trails of Marsh-Billings-Rockefeller National Historical Park are groomed for cross-country skiing and snowshoeing, with more than 12 miles of trails maintained by the Nordic Center on Route 106. A day ticket or season pass is required.
For downhill skiing, Saskadena Six is the closest ski area to the village, and Killington, Pico and Okemo are all within about an hour’s drive. A ski day fits in well before or after Christmas.
Back at the hotel, the indoor pool, cedar sauna and hot tub are ready for cold legs after a day outside.
Planning a Christmas Stay at On The River Inn
On The River Inn sits on around six acres beside the Ottauquechee River, minutes from Woodstock Village. It gives you an easy base for Wassail Weekend, Billings Farm and ski days, with somewhere comfortable to come back to each evening.
Planning around Wassail Weekend, December 11 to 13, 2026? Book early to get the room you want. From the inn, it is a short drive to the parade-day shuttle at Woodstock Union High School, and once the luminaries are lit on the Green you can come back for a swim, a sauna and dinner at 506 Bistro & Bar.
Riverview rooms face the river, and the Farmhouse Suites offer one or two bedrooms for families and friends staying together over the holidays. Compare every option on our rooms page.
Staying a few nights? Check our current offers before you book. Bringing your dog for the holidays? Designated pet-friendly Pond Ridge rooms are available, with complimentary Wi-Fi and parking for every
guest.
Frequently Asked Questions
When is Wassail Weekend in Woodstock in 2026?
Wassail Weekend runs from Friday, December 11 to Sunday, December 13, 2026. The Wassail Horse Parade takes place on Saturday, December 12, at 2pm, followed by the Memory Tree lighting and yule log bonfire at 3pm.
Is Billings Farm & Museum open on Christmas Day?
No. Billings Farm & Museum is closed on December 24 and 25. Its Winter Celebration reopens on December 26 and runs daily through January 3, 2027.
How close is Woodstock to ski areas?
Saskadena Six is the closest ski area to Woodstock. Killington, Pico and Okemo are all within about an hour’s drive, making Woodstock a convenient base for a ski day during a holiday stay.
Where can I stay for Wassail Weekend in Woodstock?
On The River Inn sits beside the Ottauquechee River, minutes from Woodstock Village and a short drive from the Wassail Weekend shuttle. Book early for December 11 to 13, 2026, as it is the town’s signature holiday weekend.
What is the weather like in Woodstock at Christmas?
December in Woodstock is cold and often snowy, with an average high of about 34°F, an average low of about 14°F and around 17 inches of snowfall, though a white Christmas is never guaranteed. If you are driving, snow tires or all-wheel drive make country roads easier after a storm.
What should I wear to Wassail Weekend?
Dress in warm layers with a waterproof coat, hat, gloves and boots with good grip. The parade, tree lighting and luminaries all take place outdoors on the Green between 2pm and 4pm, so plan to spend a couple of hours outside.
Is Woodstock walkable in winter?
Yes. Woodstock Village is compact, and the Green, the Middle Covered Bridge, Central Street and Elm Street are all within a short walk of one another, so you can park once and get around on foot. Sidewalks can be icy after snow, and the sun sets a little after 4pm in mid-December, so plan outdoor time earlier in the day.