Vermont is known for its skiing during the winter months, but after some half-hearted efforts in my younger years, I would much rather sit inside the lodge by the fire, cocoa in hand. So is there any reason to endure the cold Vermont temperatures and mounds of snow if you aren’t taking advantage of traditional outdoor winter activities?
Last March (which is still winter in Vermont, trust me) I headed to charming Woodstock to find out. Once dubbed the “The Prettiest Small Town in America” by Ladies Home Journal magazine, Woodstock contains all the elements of a quintessential Vermont town with a town green, covered bridge, white church, general store, and an iconic inn.
First on my list of things to do in Woodstock, VT?
Check Into a Cozy Inn
When cold weather hits, the most important thing to me in accommodations is a cozy, comfortable vibe. I was invited to stay at 506 On the River Inn, and in reviewing their website I could see it would check that box with premium bedding, an easy chair and ottoman in every room, and a large fireplace in their lounge area. Plus, towel warmers in the bathroom!
After a satisfying lunch at Bentleys, a local favorite, my friend and I checked in. The first thing we noticed was the massive antique desk in reception which sets the tone for the inn’s decor. The interior is outfitted in neutral shades, and although newly furnished the common areas are accented with vintage antiques and collectibles to create a modern country feel.
Neutral decor creates a calming environment. 
The breakfast buffet is served in a farmhouse style kitchen. 
The hotel common areas are decorated with vintage items. 
There is a beautiful view of the river from the inn’s porch.
After dropping our bags and taking a handful of complimentary cookies for the road, we set out for our next destination.
Sugarbush Farm
Raise your hand if you know what happens in early “spring” in Vermont. You guessed it! Time for maple syrup. You won’t find the fake stuff in any Vermont restaurant worth its salt as Vermont is the maple syrup capital of the United States, and Sugarbush Farm in Woodstock contributes to its supply with over 7,000 sugar maple trees that are tapped for their sap each year.
After a drive down a narrow paved road that turned into a narrow gravel road, we arrived at Sugarbush Farm. As stated on their website, half of Vermont roads are unpaved due to cost and because many Vermonters prefer them that way for horseback riding and other outdoor pursuits. Keep that in mind, and wear your boots too!
Each tree at Sugarbush Farm generates enough sap to make about a quart of maple syrup each year. The syrup is produced the old-fashioned way by boiling down the sap over a wood fire in the sugar house. We visited the sugar house after saying hello to the farm’s ponies, and the inside was warm and steamy from the fire.
From there we made our way to the farmhouse gift shop and tasting room. It was fun trying each of the four grades of maple syrup: Golden, Amber, Dark, and Very Dark. Maple syrup is graded by color and intensity of maple flavor. Turns out I’m an Amber girl, which is a good flavor for everyday use. From there we sampled some of Sugarbush Farm’s fifteen types of cheese, which they produce using traditional methods as well.
After purchasing our favorite flavors of syrup and cheese, and some maple candy for good measure, we went back to the village for cocktails and dinner at the Red Rooster, enjoying a long conversation with a local couple at the bar. After visiting for many years, they retired in Woodstock from the Boston area. It’s that kind of place!
A Village Walk
The best way to get to know a place is by taking a walk, and after a wonderful night’s sleep I ventured out alone early the next morning for a cold albeit sunny walk around Woodstock village. The bracing air woke me right up and it felt good to be outside as I wandered past the beautiful homes and other buildings on The Green.
From there I made my way to the Main Street of the village, past numerous storefronts housed in historic brick buildings. A turn on to Elm Street led me past more historic village homes, and eventually across the Elm Street Bridge allowing me a stunning view of the Ottauquechee River.
You can hear the rushing water of the Ottauquechee throughout Woodstock as it wends its way through the village, and both the Elm Street Bridge and Middle Bridge on the Green afford beautiful views.
Interestingly, there are six Paul Revere bells in Woodstock, VT, meaning they were crafted in Paul Revere’s foundry. There is even a self-guided walking tour that will help you locate each one, which I will have to try next time I visit. Fun trivia!
My brisk walk was rewarded with hot coffee and a huge country breakfast back at 506 On the River Inn (included with your stay). My friend and I enjoyed reading the paper and catching up on the oversized couch in front of the fireplace before heading out to do a little shopping.
Do a Little Shopping
Woodstock, VT has more than its fair share of quaint shops, boutiques, art galleries, and eateries. We spent an afternoon browsing and especially enjoyed the Yankee Bookshop and Danforth Pewter which sells pewter handcrafted in its workshop in Middlebury, VT.
Thomas Danforth II opened a pewter workshop in Connecticut in 1755, and generations of the family followed him in the pewter trade to become one of the leading families in American pewter.
F. H. Gillingham & Sons is a must do as well. In business since 1886, it is still run by the great-grandsons of Frank Henry Gillingham and is a true Vermont general store experience, mixing traditional products with new and providing visitors with a little dose of local history. Order from a list of their most popular items once you get home if you need a little taste of Vermont.
Quechee Gorge and Simon Pearce
Our last stop as we began the journey home was just a short jaunt from Woodstock in Quechee, VT. Quechee is renowned for two things, one natural and one manmade: Quechee Gorge and Simon Pearce glass.
We parked near Quechee Gorge Bridge first and walked over to look down at the Ottauquechee River from 168 feet above. It’s not for the faint of heart, especially with cold winter winds! The conditions were quite icy so we weren’t up for hiking the trails, but others were braving them.
During the Ice Age, a massive glacier covered North America. As the glacier receded, melting waters cut into the bedrock ridge and created the gorge that is considered to be the most spectacular natural wonder in Vermont. The view took my breath away!
Detail of the Quechee Gorge Bridge, the oldest surviving steel arch bridge in Vermont. 
The icy view of Quechee Gorge from the Quechee Gorge Bridge. Made me gasp a bit! 
The glassware at Simon Pearce looks delicate but is made for everyday use. Such sparkle! 
View of the partially frozen Ottauquechee waterfall and the covered bridge from inside the Simon Pearce Flagship Store.
Next stop: the Simon Pearce Flagship Store which sits on the banks of the Ottauquechee River. It has other retail locations, but the flagship store is where you can see Simon Pearce artisans demonstrate the craft of glass-blowing. It’s mesmerizing to watch a blob of orange molten glass be shaped and molded into a stunning vase, glass, or bowl.
The view at Simon Pearce is exceptional too, and in the winter the waterfall rushing just below the store is partially frozen. The acclaimed restaurant and bar at Simon Pearce were voted one of “America’s Most Romantic Restaurants” by Travel & Leisure, and the dining room commands a view of both the river and the covered bridge nearby.
Thank you to 506 on the River Inn for accommodating us and allowing us to experience Woodstock, VT and all it has to offer! A return visit is definitely in order, and below will be high on my list of things to do next time:
- Billings Farm
- Marsh-Billings-Rockefeller National Park
- Plymouth Artisan Cheese
- Vermont Antique Mall
- Horseback riding
If you MUST enjoy the fabulous skiing in Vermont, Suicide Six is right nearby and cross-country skiing and snowshoeing are available at Marsh-Billings Rockefeller National Park, among other locations. Finally, make sure you look for the Taftsville Covered Bridge, pictured below. Classic Vermont!
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[x_author title=”About the Author”]
My name is Deb Cohen, and I am a lifelong resident of Connecticut, a lover of all things historic and New England, and a realtor who helps buyers and sellers achieve their real estate goals and dreams. When I’m not working, I enjoy life with my husband, our two adult children, and our two rescue pups. Renovating and decorating our historic home, dating to 1800, is another favorite pastime.
