A Winter Travel Guide to Woodstock and Quechee, Vermont

Over the holiday break, Dan and I drove up north to explore the charming small towns of southern Vermont. First, we walked around a quaint village called Grafton, Vermont, which you can read about here. Today’s post focuses on the two neighboring towns of Woodstock and Quechee, Vermont. Woodstock and Quechee, Vermont are quintessential New England towns with a ton of fun activities, even in the winter time. In addition, these towns are close to the highway (Route-91) so they are super convenient to visit on the way up to other destinations.

Here is a map that marks all our stops within one day in Vermont.


Woodstock, Vermont

Middle Covered Bridge

Woodstock Middle Bridge in the Winter - SImply Lovebirds

Facing the town green is the gorgeous Middle Covered Bridge. The bridge leads to residential homes then loops you back out to the main road or you can take a right to reach the Billings Farm and Museum. Since it was a freezing day in December, we decided to skip the farm and head downtown instead.


Woodstock, Vermont

Woodstock Inn and Resort

Entrance of Woodstock Inn & Resort in the Winter, Vermont - Simply Lovebirds - New England Lifestyle Blog

The Woodstock Inn and Resort is a gorgeous four-star hotel located downtown. As recent college graduates, we couldn’t afford to stay here but definitely recommend staying overnight in an inn or bed and breakfast (b&b) like this when you’re in Vermont for an authentic experience.

Woodstock Inn & Resort in the Winter, Vermont - Simply Lovebirds


Woodstock, Vermont

Downtown Woodstock

Walking in snow in Woodstock, Vermont - Simply Lovebirds - New England Lifestyle Blog

We found street parking on Elm Street then wobbled in the snow to the shops and restaurants on Central Street. It was a cold day, so we hopped in and out of stores to stay warm. Unfortunately, I didn’t bring my camera out very often for pictures because I wanted to keep my hands in my pockets, but we do have recommendations on which shops to visit!

We would recommend visiting F.H. Gillingham & Sons (not pictured), a big general store with every local Vermont item imaginable lining the shelves. It was really fun to browse for different gift ideas.

Across the way was the Vermont Flannel Company (not pictured), which had the softest flannel clothes and blankets. Lastly, my favorite store on Central Street would probably be the Unicorn gift shop (not pictured) because there were so many fun trinkets to play with.

Entrance of Woodstock Pharmacy during the Winter - Simply Lovebirds - New England Lifestyle Blog


Taftsville Historic District, Vermont

Taftsville Covered Bridge

Taftville Covered Bridge in Vermont - Simply Lovebirds - New England Lifestyle Blog

In-between Woodstock and Quechee is a historic 19th-century industrial village called Taftsville. While we didn’t explore this village in-depth, we stopped to photograph their covered bridge. Then we drove across to see this really cute country store.

Quaint Country Store in Woodstock, Vermont - Simply Lovebirds - New England Lifestyle Blog


Taftsville Historic District, Vermont

Andrew Pearce Bowls

Artist in Andrew Pearce - Woodworking - Woodstock, Vermont

On our way through Taftsville, we found a sign for Andrew Pearce Bowls, so we stopped to check out his wooden collection. There were tons of wooden salad bowls, plates, cutting boards — everything wood! Overall, this store is much smaller than his brother’s store (Simon Pearce) which you will learn more about as you scroll down.

Quechee Covered Bridge in the winter, Vermont - Simply Lovebirds - New England Blog


Quechee, Vermont

Jake’s Quechee Market and Café

Entrance of Jake's Quechee Market in Vermont - Simply Lovebirds - New England Lifestyle Blog

Finally, we’ve made it to Quechee, Vermont! Since we were planning to return back to Connecticut on this day, we grabbed something quick and casual at Jake’s Quechee Market and Café. They had breakfast foods and a build-your-own sandwich option for lunch. Keep in mind, the café closes at 2pm, however, they have a deli open with soup, sandwiches, and salads that you can take to-go. We ended up buying a jug of Vermont cider to take home for later.

Menu in Jake's Quechee Market Cafe, Vermont - Simply Lovebirds - New England Lifestyle Blog


Quechee, Vermont

Simon Pearce Glassware

If you liked Andrew Pearce’s wooden work, then you will LOVE Simon Pearce’s glassware. The Simon Pearce flagship store has a huge collection of the most sophisticated handmade glassware in New England and an accompanying fine dining restaurant with a view of the Ottauquechee River waterfall and covered bridge. Simon Pearce’s work is expensive, so we just walked around the store to admire it all.

Hands-down, the best part of Simon’s Glassware was heading downstairs to see the glassblowers create work before your eyes! We spend most of our time here absolutely mesmerized, just watching them do their magic. The entire room was hot from all the glass being melted, which was exactly what we needed from a cold day outside. The artists were really nice and open to answering questions!

Gingerbread house in Vermont - Simply Lovebirds

This gingerbread house is #goals. It looks just like the Simon Pearce property, which has a view of the river and covered bridge. I would never have thought to use pecans for the roof or blue rock candy as water!

View from Simon Pearce Gallery in Woodstock, Vermont - Simply Lovebirds

Just outside the glass-blowing station was a balcony overlooking the river and covered bridge. If you ate at their restaurant, you can get the same view. Recognize this scene? This is what the gingerbread house with the pecan roof was modeled after!

Frozen river in Vermont - Simply Lovebirds


Quechee, Vermont

Quechee Gorge Village

Our last stop was the shops at the Quechee Gorge Village. We started at the Cabot Cheese Quechee Store, which had different types of cheeses and spreads that you can taste with crackers. Further in, we discovered a toy shop and this HUMONGOUS bear — it was screaming for a photo op!

Eventually we ended at the Alpaca store where I FELL IN LOVE. When I saw the shelf of little alpaca dolls (made of real alpaca fur), I started tearing up because they were the cutest balls of fluff I have ever seen, especially seeing them all sitting together. I went back and forth deciding whether to buy one because they were definitely on the pricy side. At last, I walked away defeated, then Dan ran back and bought one for me after all! Sweetest fiancé ever! He was laughing the entire time as he bought my alpaca and the guy at the register smiled as he said, “another one adopted.”

My alpaca’s name is Tina (holding her on the right). She likes to sit on the coffee table and watch TV with us 🙂



Check out our other winter travel guides around New England!

A Winter Travel Guide to Grafton, Vermont

A Winter Travel Guide to Acadia National Park, Maine

A Winter Travel Guide to Newport, Rhode Island

A Winter Travel Guide to Boston, Massachusetts