Travel Guide: Fall in Woodstock, Vermont

Plan Ahead:

1. Track The Foliage –  Each New England state offers a Fall foliage tracker with an interactive map on their state's official website. Vermont's foliage tracker can be found at 

2. Make Dinner Reservations – Dinner reservations are very hard to make last minute in Vermont since there are very limited food options. I suggest making reservations before the trip to bypass the wait or even being turned down. COVID-19 has many restaurants only allowing minimal occupancy, and it was so hard to find food. Eventually, we had to stop at a grocery store one night definitely plan ahead.

3. Rental Car- Most attractions are not within walking distance. Rental car is the best way to get around. 

What to Pack:

Make sure to pack layers. New England's Fall is usually cool in the morning, warms up during the day, and then gets cold at night. If you are planning on hiking or doing walking trails, pack appropriate footwear/gear. Be sure to leave extra space in your luggage or bring an insulated cooler because you will want to take home all the maple syrup and cheese.

Attractions in Woodstock & Around:

1. Sugarbush Farm: Our first stop Sugarbush Farm which covers 550 hillside acres. This farm is highly awarded for their esteemed cheeses. Boston Globe credits them as a “cheese lovers paradise,” and in 1995, American Cheese Society awarded a blue ribbon for the best smoked cheese in the country. This farm has received numerous other awards. Enjoy sampling their fifteen different cheeses. The cheeses were INCREDIBLE, and there was so much variety with the cheeses being produced. Since this is a family owned farm, you can also ask about their cheese making process. We ended up buying sage, jalapeño and cayenne pepper, and smoked with bacon cheddar cheeses. I was highly surprised with the sage cheddar, which was a mild cheddar with flecks of dried sage. The herb adds just the right balance with the cheese, and it pairs best with sandwiches. The cheeses are wrapped in wax and can last several days at room temperature. However, if you are planning an extended trip in Vermont, the farm recommends an insulated cooler. Upon visiting they can advise more based on season and stay for storing your cheese. 

Sugarbush also produces maple syrup. Both cheese and maple syrup! Am I in heaven? In the sample room, you are able to sample the four different grades of maple syrup. We bought the sampler pack. My favorite was the first grade. It tasted like a blend of maple syrup and caramel.  You can also visit the sugarhouse on property learn how maple syrup trees are tapped and the process of how maple syrup is made. The exhibit is open year round, however the actual process only occurs in March and April. The farm also has a walking path where you can see the trees that were tapped. The walking trail takes a total of fifteen minutes. Farm animals are on property for viewing including horses, rabbits, and cows. Even if you are not visiting Vermont and still want to taste their cheese or syrup, they do have an online website. I will link here. This farm is free to the public. 

2. Billings Farm: Founded by Laurance and Mary Rockefeller in 1968. It is now owned and operated by The Woodstock Foundation, Inc., a non-profit to preserve the farm and rural culture of Vermont. Billings Farm is known for breeding jersey dairy cows, sheep, draft horses, and oxen. Admission price is $16 per adult. I recommend starting with the theater as it shows a very informational video (30 minutes) about the history of the farm. A piece of American history with some of the oldest archived agricultural history. The barns are closed due to COVID-19 precautions, but one is still open to be able to view the animals grazing in the pastures. There is also an interactive museum that is multi levels for depicting farm life over the years. There is a walking trail that is an easy one mile loop around the farm and there is even a dairy bar. We decided to try their Vermont made ice cream I got the maple sundae and apple cider donuts yum. 

3. Downtown Woodstock: Downtown Woodstock is one block of shops and dining. My favorite store was FH Gillingham & Sons General Store. I loved the variety including maple syrup, New England canned chowders, and different spices. I wanted to stop in The Vermont Flannel Co. however there was an hour wait to get in. The company sells everything flannel from attire to blankets. It will be on my list for the next time I visit! 

4. Admire the Covered Bridges: Middle Covered Bridge is in downtown, Woodstock. You can walk to this bridge right near all the shops and dining. The Lincoln covered bridge is a historic covered bridge and there is also Taftsville bridge. 

5. Scenic drive or hike. We decided to take a scenic drive around the area. This rural town boosts beautiful views of the Vermont fall foliage. Next year, a beautiful hike is on my list. 

Places to Stay:  


Woodstock Inn-Set in the middle of downtown Woodstock. Be steps away from all shops and dining. This historic inn has multiple culinary experiences and chic spa. 

The Jackson House Inn-A beautiful crafted inn with character. Features 3 acres of beautiful landscape.


Windsor Mansion Inn-We stayed at this inn about 30 minutes from downtown, Woodstock. The inn with impressive views of Lake Runnemede, the Cornish Hills, and Mount Ascutney. Prominent figures who have stayed at this inn included Presidents Roosevelt and President Wilson. I LOVED the service here. The rooms were quaint. We arrived late in the evening and welcomed to a outdoor fire pit with marshmellows. Plus, FREE morning coffee/tea bar. I highly recommend booking a stay here. 

The Quechee Inn at Marshland Farm- Listed on the National Register of Historic Places, the inn maintains 19th century elegance. Each room different style and story to tell.  Views include Dewey’s Mill Pond and the Ottauquechee River, 


Best Western Lebanon NH-Although this hotel is in New Hampshire. It is 25 minutes from downtown Woodstock. Has modern luxuries. Plus, if you stay at Best Western frequently start earning points. 

Hotel Coolidge-Listed on the national register of historic places. An updated inn located in White River Junction, VT. This inn is 25 minutes from downtown Woodstock, VT. Steps away are local dining and antique stores. 


This plaid blazer makes any look chic. Especially dressing it down with jeans gives you a whole put together look! I do recommend a mock neck WOOL sweater or wool blend it will keep you warm throughout fall and winter and become a staple piece. Especially if creating a capsule wardrobe a mock neck will be in your closet for years to come. 

  • Taylor Bush
    Posted at 5:28 am, November 24, 2020 Reply

    Oh Vermont looks gorgeous in Autumn! Beautiful pictures!

  • Taylor Bush
    Posted at 11:25 am, November 23, 2020 Reply

    We just visited this area and went to Sugarbush Farm. We loved it too!

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