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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?

The Woodstock Inn & Resort

The Woodstock Inn & Resort in Woodstock, Vermont.

Aimee Seavey

woodstock inn vermont christmas

The Woodstock Inn & Resort dressed up for the holidays.

Aimee Tucker

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…

woodstock inn vt fireplace

Is this the coziest fireplace in New England?

Aimee Seavey

woodstock inn gingerbread house

The life-size “gingerbread house” in the lobby of the Woodstock Inn, decorated with real candy!

Aimee Seavey

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

woodstock inn vt conservatory

The sunny conservatory at the Woodstock Inn is the perfect place to enjoy your morning coffee.

Aimee Seavey

The Woodstock Inn library.

The Woodstock Inn library.

Aimee Seavey

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.

The Woodstock Town Hall Theatre.

The Woodstock Town Hall Theatre.

Aimee Seavey

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.

wassail weekend woodstock vt house tour

During the Holiday House Tour, shoes had to be taken off…and booties put on…to help keep the carpets clean. Sadly, interior photos were also not allowed.

Aimee Seavey

woodstock historic house tour eyebrow

Stops along the tour included this 1840’s “eyebrow Cape,” so named for its signature sharply pitched roof over the front door.

Aimee Seavey

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…

woodstock vermont covered bridge

Middle Bridge in Woodstock, Vermont is the quintessential New England covered bridge.

Aimee Seavey

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

woodstock vermont

A view of the courthouse and library from the Woodstock Green.

Aimee Seavey

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

Holiday cheer in Woodstock, Vermont.

Holiday cheer in Woodstock, Vermont.

Aimee Seavey

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.

woodstock vt parade sign

The Woodstock Green readies for the Wassail Parade.

Aimee Seavey

woodstock vt yule log

The town Yule Log, waiting to be lit.

Aimee Seavey

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

woodstock vt pharmacy

The Woodstock Pharmacy.

Aimee Seavey

bentleys restaurant woodstock vt

Bentley’s Restaurant, which is famous for the sea of ornaments that hang down from the ceiling during the holiday season.

Aimee Seavey

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

woodstock vermont yankee book shop

The Yankee Book Shop.

Aimee Tucker

R.T. Home in Woodstock, VT

R.T. Home.

Aimee Seavey

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

The Vermont Flannel Company.

The Vermont Flannel Company.

Aimee Seavey

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.

The Woodstock Inn wagon for the Wassail Parade.

The Woodstock Inn & Resort wagon for the Wassail Parade.

Aimee Seavey

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…

wassil parade 2015

A sampling of some of the parade’s 4-legged stars.

Aimee Seavey

wassail parade woodstock vt carriage

Handsome participants in the Wassail Parade.

Aimee Seavey

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?!

wassail parade woodstock vt bw

Is this the 19th or 21st century? Kind of hard to tell with equipment and costumes this good!

Aimee Seavey

Now that’s more like it…

wassail parade woodstock horse

Phil Warren poses with Mike…or maybe Max.

Aimee Seavey

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!”

wassail parade horse

Scenes from the Wassail Parade.

Aimee Seavey

Wassail Parade church

Approaching the First Congregational Church during Woodstock’s Wassail Parade.

Aimee Seavey

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.

wassail parade gillingham

Crowds line up in front of Gillingham’s General Store to enjoy the Wassail Parade.

Aimee Seavey

wassail parade woodstock green

Rounding the Woodstock Green during the Wassail Parade.

Aimee Seavey

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

wassail parade santa

Don’t miss Santa!

Aimee Tucker

…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.

wassail parade woodstock skater

Maybe the most applauded parade participant — the man who rollerblades in a top hat at the parade’s end with his trusty shovel.

Aimee Seavey

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!

woodstock wassail weekend yule log

The yule log burns low as the sun sets over Woodstock.

Aimee Seavey

wassail weekend sunset

The Woodstock green at sunset.

Aimee Seavey

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 Wassail Feast at the Woodstock Inn.

The Wassail Feast at the Woodstock Inn.

Aimee Seavey

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!

Billings Farm and Museum in Woodstock, Vermont.

Billings Farm and Museum in Woodstock, Vermont.

Aimee Tucker

Billings Farm and Museum in Woodstock, Vermont.

The lovely landscape at Billings Farm and Museum in Woodstock, Vermont.

Aimee Seavey

billings farm animals

The animals at Billings Farm include horses, sheep, chickens, and Jersey cows. The little one in the lower left was just 3 days old!

Aimee Seavey

Billings Farm and Museum in Woodstock, Vermont.

The 1890 Farm House at Billings Farm.

Aimee Seavey

Billings Farm and Museum in Woodstock, Vermont.

It’s Christmas in the 1890 Farm House.

Aimee Seavey

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. 

The post Wassail Weekend | Holiday Fun in Woodstock, Vermont appeared first on New England Today.



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