6 Things To Do In Woodstock, VT During Fall

Woodstock, Vermont is named the prettiest town in America and it lives up to the expectations. The quintessential New England town is a great spot to visit year around. Spring and summer for hikes, fall for the foliage, winter if you are a skier. In my opinion- October is the best time to visit Woodstock, VT. I describe it as stepping into a mix of Halloweentown and Stars Hallow from Gilmore Girls. Here are all my favorite things I did in Woodstock, Vermont!

PLANNING TIPS

  • If your goal is to see foliage, use a foliage tracker to plan your trip. For reference in 2020, I went October 11 and in 2021 went October 8th, both at prime foliage.

  • Book in advance. Hotels and airbnbs are limited and fill up quickly during peak time. Adding on to that- make as many dinner reservations as you can. We got turned away from so many different restaurants since there isn’t a ton of options that can hold the bigger crowds from the tourists coming in.

  • You will definitely need to either have a car or rent one during your time here. Uber’s aren’t as common as in other areas in the country.

THINGS TO DO

Walking around downtown Woodstock


Charming, cozy and inviting. A place like this makes me want to quit my 9-5 job in the city, move here and open a bed and breakfast. Life is much more simple here in comparison to living in New York City like I do. Grab a coffee, your favorite flannel and scroll though downtown to various shops, restaurants and gorgeous colonial homes. The best part of starting off here- it’s free!

Stops to make while walking around-

  • Woodstock Inn

  • The Woodstock Middle Bridge

  • Yankee Bookshop

  • F.H Gillingham & Sons

This town does not forget about fall decor

Covered Bridge in Downtown

2150C62D-8442-4F61-995B-7E56C4624C92.jpeg

Billings Farm

Address: 69 Old River Rd, Woodstock, VT 05091

Billings Farm is located a quick walk from downtown Woodstock and is a working farm and museum. You pay a small fee to get in and can enjoy exhibits on how farming has evolved in the last hundred years, see all of the farm animals and enjoy the beautiful Vermont views.

Sugar Bush Farm


Address: 591 Sugarbush Farm Rd, Woodstock, VT 05091

Sugar Bush Farm is a famous family owned farm where you can try their homemade syrup and cheese. Enjoy the scenery, free samples and learn more about the production of maple syrup across the 500+ acres of land.

Warning: be careful when coming to Sugar Bush Farm. It’s on a dirt road that is filled with hills and big rocks. If you have 4 wheel drive this would be the time to use it. Last year it cost me $1,500 in repairs on my car after hitting a rock and it splitting a pipe underneath my car.

Quechee Gorge

Address: 5800 Woodstock Road Hartford, VT 05047 United States

One of the nature gorgeous creations- the Quechee gorge is 165 feet deep and is the deepest gorge in Vermont. You can see the gorge from a bridge of the highway or there is also trails to walk to the other end of the gorge and plenty of parking nearby.

Antique Market

Address: 5573 Woodstock Rd, Quechee, VT 05059

While in the area visiting the Quechee Gorge, not far is the Quechee Gorge Antique Mall. Inside this 17,000 square feet barn is hundreds of booths of antiques, a general store and an area to sampling Vermont’s best cheese! Make sure you continue looking around back to feed some alpacas.

Driving Around

Even though just driving around isn’t much of an activity to some people, there is magic aimlessly driving around Vermont during this time of year. Tree lined roads, billowing fields, historic farm homes and paths through the yellow, orange and red foliage that only last for a short but sweet time in October.

Some popular areas to drive through-

  • Old River Road

  • Cloudland Road

  • Galaxy Hill Road

  • Old Stage Road

  • Route 4

Thank you for reading and enjoy your trip to Woodstock, VT! xo

Jenna WillardComment