New England in the Winter

Woodstock, Vermont

Our family has many holiday traditions. My favorite of them is Woodstock.

Each year after Christmas, we begin the journey from Connecticut to Vermont. For a short trip we manage to pack a lot of things in the car. For years, my sister and I have been wedged in between L.L. Bean bags with christmas cookies, snowshoes, miscellaneous presents and our Mom’s fur is usually draped across our laps.

It is here that we ring in the New Year with close friends and family.

Woodstock Covered Bridge

JB Reed Photography

A true New England town, Woodstock has deep history. Chartered in 1791, the Rockefeller Family has helped preserve the town’s charm and protect it’s 19th century architecture– conserving the rolling ridge line, burying power lines and building the iconic Woodstock Inn which sits at the foot of the town square called, The Green.

In “popular culture” and I put that in quotes because I don’t know how popular or cultural this is– one of the famous, and I think the first, Budwiser holiday commercials with the Clydesdales was filmed in Woodstock.

While not filmed in Woodstock,here was my favorite commercial of the series aired only once as a 9-11 tribute.


Woodstock in the Winter: Eating, Staying and Playing

Woodstock Inn

JB Reed Photography

The Billings Farm and Museum:

This is an operating dairy farm and a museum of Vermont’s Rural Past. Doesn’t sound fun right? It is.

First, the are horse drawn sleigh rides in the winter. They put tartan plaid wool blankets on your lap and off you go with hot cider in hand. Next you can go visit the animals. As you enter the barn you are greeted by the giant Draft Horses– Belgian and Clydesdale horses are part of this family. They are awe inspiring and gigantic. Next, there are baby cows. This year we pet one who was only 4 days old. Lastly, there is the sheep pen- my absolute favorite part of the farm. These are not well manicured sheep and they smell, but they are adorable.

The best part of the farm is that it is rooted in conservation- it’s original owner planting more than 10,000 tress in the Woodstock area. It is supported by the Woodstock Foundation which reflects the conservation and sustainable land use philosophy of it’s founders Laurence and Mary Rockefeller.


Simon Pearce

Simon Pearce:

Located in Queeche, Vermont, about 15 minutes outside of Woodstock, is Simon Pearce. This gorgeous building is a place of fine artistry where hand blown glass creations are made. Next to a picturesque frozen water fall, you can watch craftsmen make some of the most gorgeous high end champagne flutes, vases and serving pieces. It is also an incredible restaurant that we visit annually.

The cover of their book features my favorite bowl.

Blue Horse Piano

Image curtsey of The Blue Horse Inn

The Blue Horse Inn

After 25 plus years of winters at the Woodstock Inn, we found ourselves longing for the Inn we used to know where families read by the fire, wild board games were waged in the Library and the Front Desk staff would find the Popple we accidentally left at Tea Time and bring it back to us with a smile.

The Blue Horse Inn is all of that with a locally sourced gourmet Vermont breakfast, a wine hour, outdoor wood fired hot tob and  gorgeous accents like sterling silver bon bon sugar tongs which I just fell in love with.

The owners are wonderful and we have started a new family tradition. We are happy to have our whole group under one roof where we can enjoy the fireplace and maybe one day our friend Rob who is classically trained on the piano will agree to serenade us.


Other Activities I love:

Gillingham & Sons General Store is a Woodstock favorite. It is here you can get a fancy beer that my husband likes, some authentic Vermont Maple Syrup, the legendary children’s book Miss Rumphius, a pair of one piece pajamas and an ax. How does one store have some many amazing things? Unclear, but they do.


There is a star that shines above the town of Woodstock which twinkles on cold winter nights. Hiking or snowshoeing to the star is a great activity. If you are brave or have a headlamp, hike up and wait for it to turn on for a special night. We did that on December 31st of 1999.

The Woodstock Inn Nordic Center is a great place to rent X-Country skis and begin a fun day of exercise on their trail network. Warning– there is terrain which slopes downhill. I took my close friend from Greenwich Academy, Charlie, on a trail called “Trail of the Fallen Women”. Despite nearly two decades of friendship I think she is still mad about it.