Wassail Weekend | Holiday Fun in Woodstock, Vermont

Often named one of the prettiest small towns in America, the village of Woodstock, Vermont becomes the ultimate holiday destination during its annual Wassail Weekend. In fact, we love Woodstock at Christmas so much we paired it with Manchester, Vermont for the Yankee Magazine November/December 2015 cover story (Christmas Celebrations in Woodstock and Manchester, Vermont), and featured the town’s most famous hotel, the Woodstock Inn & Resort, on the cover!

This year, at the invitation of the Woodstock Inn, I headed to Vermont to take part in the event, which is also included on Yankee‘s list of Best Christmas Celebrations in New England. The nonstop schedule of fun includes multiple concerts, craft fairs, a holiday house tour, parade, community yule log, and much more (this year’s event is scheduled for December 13-15, 2019). Ready to wassail?

Inside the Woodstock Inn, which has a history that stretches back to 1792, the scene is picture-perfect coziness, from the massive and cracking fireplace and life-size gingerbread house in the lobby…

…to the beautifully decorated conservatory, library, and beyond.

So just how old is the Woodstock Inn? In 1969, Laurance S. Rockefeller, grandson of John D. Rockefeller (Laurance was a Woodstock resident by marriage, but then a fan for life) was approached to renovate the existing structure, which was badly in need of repairs. He deemed it un-salvageable, but replaced it with the current building. Alongside its 19th-century neighbors, you’d hardly know the inn is much newer. Attention to historic detail and beauty is a Woodstock virtue.

After a wonderful jazz performance at the Town Hall Theatre on Friday evening, we made our way back on Saturday morning to pick up our materials for the annual Holiday House Tour, presented by the Pentangle Council on the Arts.

This year’s tour included 9 properties, all within walking distance from one another, although a horse-drawn wagon was also making the rounds should you prefer a ride instead.

As we popped into the “houses” (which included a few artists’ galleries, the Woodstock Historical Society, and refreshments at The Prince & Pauper Restaurant), we also enjoyed strolling Woodstock’s impossibly charming elliptical village green.

What do I mean by “charming?” The better question is, what don’t I mean? Popular sights bordering the green include the 1969 town lattice Middle Bridge that spans the Ottauquechee River…

…lovely brick buildings, like the town library and courthouse…

…and numerous other examples of New England architecture and holiday decor.

During Wassail Weekend, the green is a popular spot to watch the Wassail Parade, and is home to the yule log (which looks more like a mini-bonfire) and hundreds of evening luminaries.

Downtown, which is just steps away, Woodstock’s businesses were also looking marvelously festive, from pharmacies, general stores, and cozy restaurants…

…to bookstores, gift shops, antique stores, and home furnishing shops.

Some spots, like the Vermont Flannel Company, appear ready for the holiday season all year long.

Wassail Weekend is packed with fun and festive events that run from morning ’til night, but its highlight has to be the Wassail Parade, which kicks off just after lunch on Saturday, and is sponsored by the High Horses Therapeutic Riding Program and the Woodstock Area Chamber.

When the Woodstock Inn asked if I might like to experience the parade from their own “float,” which (in Wassail Parade terms) meant a decorated wooden wagon, I immediately said yes.

In the pre-parade gathering area, the 4-legged participants in the parade, while ranging in size, were equally festooned in holiday finery. Some more willingly than others…

Here’s the Woodstock Inn’s wagon, along with its skilled and patient team (including horses Mike and Max). It’s amazing what a little photo filtering can do. What century is this?!

Now that’s more like it…

Spanning the entirety of downtown, the Wassail Parade winds past the stately First Congregational Church before circling the town green and the Woodstock Inn, where each entry is formally announced. Throughout the route, upbeat crowds lined the street, waving and clapping and calling out “Merry Christmas!”

The merriment of the parade, paired with the Christmas-drenched scenery of Woodstock (a town already celebrated for its visual charms), is an utter delight. This year’s warm temperatures also led to (what I was told were) “bigger than ever” crowds, which only added to the fun.

At the parade’s end, Santa rides past in his own wagon…

…and then, right on cue, the unofficial star of Wassail Weekend (in my opinion, anyway) emerges. Strapped into rollerblade “skates” and sporting a top hat, he zips around, shoveling up the “presents” left behind by the ponies, donkeys, and horses. Now there’s a man who deserves to be on Santa’s Nice List.

After the parade, as the yule log burned low, the 400 glowing luminaries were lit by volunteers. This year, we were also treated to a gorgeous sunset that made the whole affair just that much rosier. What a beautiful evening to be in Woodstock!

Hungry, we headed back the Woodstock Inn for its annual family-style Wassail Feast. Featuring dishes like Colcannon Potato Soup, Rosemary Roasted Cornish Game Hen, and Herb Crusted Atlantic Black Cod with sticky toffee pudding and English trifle for dessert, we enjoyed the good company of our fellow diners, and ate until we were stuffed. What a feast!

The next morning (after a luxuriously comfortable sleep), we concluded our Wassail Weekend with a visit to Billings Farm and Museum, located just a few minutes drive away.

In December, the museum focuses on how Christmas was celebrated in late 19th century Woodstock through historic and farming exhibits, interactive crafts, live animals, and an 1890 farm house decorated for the season. There are also horse-drawn sleigh or wagon rides, as the weather permits.

Billings Farm is a wonderful spot to visit year-round, but their holiday program is especially nice. In fact, we like it so much we’ve also included it on our list of the Best Historic Christmas Celebrations in New England!

The perfect historic ending to a beautiful, fun, and festive Wassail Weekend in Woodstock!

Have you ever visited Woodstock, Vermont?

This year’s Wassail Weekend will take place on December 13-15, 2019. Don’t miss it!

Special thanks to the Woodstock Inn for coordinating our visit. We had a wonderful time.

The Woodstock Inn & Resort. 14 The Green, Woodstock. 888-338-2745; woodstockinn.com
Billings Farm and Museum. 5302 River Road, Woodstock. 802-457-2355; billingsfarm.org
Woodstock Chamber of Commerce. 59 Central Street, #2, Woodstock. 802-457-3555; woodstockvt.com

This post was first published in 2015 and has been updated. 

Aimee Tucker

Aimee Tucker is Yankee’s senior digital editor. A lifelong New Englander and Yankee contributor since 2010, Aimee has written columns devoted to history, foliage, retro food, and architecture, and regularly shares her experiences in New England travel, home, and gardening. Her most memorable Yankee experiences to date include meeting Stephen King, singing along to a James Taylor Fourth of July concert at Tanglewood, and taking to the skies in the Hood blimp for an open-air tour of the Massachusetts coastline.

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