A Travel Guide to Woodstock, Vermont

To celebrate our 5 year wedding anniversary, Rob & I snuck away to Woodstock, Vermont for a long weekend. Traveling to Vermont during Fall and the peak foliage season has been on my bucket list for awhile now. As we drove north toward Vermont, the leaves began to burst with all their bright colors! The weather was mild the entire weekend and the scenery was so incredibly beautiful that we spent most of the weekend outdoors taking it all in.

Woodstock is located on the banks of the Ottauquechee River and is a 2 1/2 hour drive from central CT. Named one of the “prettiest small towns in America,” Woodstock features an idyllic “Green” lined with historic homes, 3 covered bridges, and a national park (one of two in the whole state of Vermont!). It really is a pretty place to visit in any season, but during the Fall the town definitely shows off!

Where To Stay

We drove down Center Street past the shops and the large green and turned into the private parking lot for the Blue Horse Inn. The Inn has so much charm and every room felt perfectly decorated, but still cozy. When we got there, the owners, Jill & Tony, gave us a tour of the property. The grounds were super impressive with a charming back porch, a pool, and Adirondack chairs throughout the yard where guests can take in the views. From the Inn’s yard, we enjoyed views of the river and Middle Bridge, and all the beautiful foliage. My other favorite thing about the Inn was the incredible breakfast. The breakfast was out of this world, with different options each day and seasonal entrees featuring local ingredients. From the BlueHorse Inn, we could walk into Town and to all the restaurants. I plan to write another post on all the details of our stay at the Inn because we enjoyed our experience so much.

Another lodging option is the Woodstock Inn & Resort. The Resort is the largest hotel in the area with 142 guest rooms, a ton of amenities, including a few restaurants, a spa, and a golf course. Rob & I visited the Resort for an after dinner drink and sat by the large fireplace in the lobby. It is beautiful and would be a great option for families. The Woodstock Inn dates back to 1793 and was once owned by the Rockefellers.

Where To Eat

One thing I learned quickly is it is very important to make dinner reservations in advance. There are not that many restaurants in the area and with current COVID restrictions, everything books up really quick. When we arrived, we grabbed lunch at Mont Vert Cafe, a popular spot for breakfast and lunch. They offer both online ordering and in person eating. We grabbed sandwiches (the Gobble It Up – yum!) and a cappuccino and ate upstairs by the window. For dinner, we made reservations at the Lincoln Inn & Restaurant at the Covered Bridge for a special anniversary dinner. This was a unique food experience featuring a 7-course tasting menu (and optional wine pairing) by Chef Jevgenija Saromova. Typically, you dine outdoors in a clear lit up gazebo, but unfortunately due to the rain earlier in the day, dining outdoors was not an option. Even without the outdoor experience, the food was delightful and my inner foodie loved every minute of it! We did it up that night, opted in for the wine pairing, and dined on Japanese Wagyu Tenderloin, White Sturgeon Cavier, Deconstructed Caprese Salad, and other one-of-a-kind culinary dishes.

On Day 2, we drove to the Woodstock Farmers Market and picked up sandwiches to go. This was a really neat market with lots of local products. For dinner, we made a reservation at Prince and the Pauper, and enjoyed a delicious classic meal in the heart of Woodstock. They also have seasonal cocktails, like the Hot Mulled Cider With Rum. This warmed me up real quick!

A few other options that were highly recommended, but we couldn’t squeeze in were Mangalitsa, Richardson’s Tavern, Red Rooster, and Worthy Kitchen.

What To Do

For Woodstock being a pretty small town, there was so much to do during our time there. We originally wanted to explore surrounding areas of Vermont, but we ended up staying busy in Woodstock the entire weekend. On our first full day, we finished breakfast and starting walking from the Inn to the start of Faulkner Trail, a part of the Marsh-Billings-Rockefeller National Historic Park. Along the way we walked through the Middle Bridge (pictured above) and beautifully situated homes decorated for the Fall season. We approached the trail and started are way up the winding path. The trail itself was well traveled, easy to hike, and well marked all the way up to the top (about 1 1/2 miles). Once we got to the top, we sat and took in the views of the town and the colorful foliage. We made our way down the other side of the mountain, hiking to the Pogue – a pond, and back to town. The whole loop was about 4 miles, but there are a variety of trails throughout the Park to lengthen or shorten the total trip. On our way back we passed Billings Farm, a full operating dairy farm, and saw the horses running in the field.

After we got back and cleaned up, we spent the rest of the afternoon walking through town, checking out the shops, antique stores, and local sights. A few of my favorites were the Yankee Book Shop (VT’s longest running independent bookstore), Clover Gift Shop, The Vermont Flannel Company, Farmhouse Pottery and FH Gillingham & Sons – Vermont General Store.

The next day, we drove to Sleepy Hollow Farm (pictured below). I had seen so many photographs of this farm and wanted a chance to see it in person. The farm itself is breathtaking and definitely makes a great photo opportunity. From there we headed to Sugarbush Farm to taste locally made cheese and maple syrup. Both were so good! We bought the lightest maple syrup to take home with us and a bunch of fresh cheese. Our last stop was at the Taftsville Covered Bridge, which is conveniently located on the way home to Connecticut.

Some other ideas if you have more time: A trip to Quechee to see the Quechee Gorge Village and the Quechee Gorge, Long Trail Brewing Company, Harpoon Brewery, and Simon Pearce.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.