6 Things To Do In Woodstock, VT During Fall
Woodstock, Vermont is the kind of town that feels almost too perfect to be real. With charming New England homes, covered bridges, local shops, farms, and beautiful fall foliage, it's easy to see why Woodstock is one of my favorite places to visit in Vermont.
I've visited Woodstock in October multiple times, and in my opinion, fall is the best time to experience it. I describe the town as a mix of Halloweentown and Stars Hollow from Gilmore Girls—cozy, charming, and completely magical when the leaves change.
If you're planning a fall trip to Vermont, here are my favorite things to do in Woodstock, from exploring downtown and visiting covered bridges to farms, scenic drives, and nearby day trips.
Planning a Fall Trip to Woodstock
When is the best time to visit Woodstock?
If you're visiting Woodstock specifically for fall foliage, October is my favorite time to go. I've visited in October multiple times, including October 8 and October 11, and both trips had beautiful fall color.
Peak foliage changes every year, so I recommend checking a foliage tracker before planning your trip. If seeing the leaves is your main goal, try to be flexible with your dates rather than choosing a weekend months in advance.
→ Check the New England foliage forecast
Book your stay early
Woodstock is a small town, and accommodations can fill up quickly during peak foliage weekends. If you're visiting in October, I'd book your hotel or vacation rental as early as possible.
I'd also recommend making restaurant reservations ahead of time. During our visits, we had trouble getting into some restaurants without reservations because the town gets especially busy during peak foliage.
Do you need a car?
Yes, I would definitely recommend having a car for a Woodstock trip. While the village itself is very walkable, many of the farms, scenic roads, and attractions are outside the center of town. Uber and other rideshare options are also much less common than they are in larger cities.
THINGS TO DO
explore downtown Woodstock
This is probably my favorite thing to do in Woodstock. The town is charming, cozy, and incredibly easy to explore on foot. Honestly, it makes me want to leave my city job, move to Vermont, and open a bed and breakfast.
Grab a coffee, put on your favorite flannel, and spend the morning wandering through the village. You'll find locally owned shops, restaurants, historic homes, and beautiful views around almost every corner.
The best part? Exploring downtown is completely free, so you can take your time without needing an itinerary.
Stops to make while walking around
Woodstock Inn & Resort
One of the top hotels I've ever had the pleasure of staying at! It's a timeless, beautiful hotel right in the heart of historic Woodstock. Even if you're not staying here, it's worth walking by and taking in the classic New England architecture.
→ Check rates at Woodstock Inn & Resort
Middle Covered Bridge
Located right in the center of town, the Middle Covered Bridge is one of Woodstock's most recognizable landmarks and an easy photo stop while you're exploring downtown.
Yankee Bookshop
Stop into Yankee Bookshop if you love independent bookstores. It's the kind of little shop that's fun to browse while wandering through town.
F.H. Gillingham & Sons
This historic general store is another fun stop for Vermont-made products, snacks, and souvenirs.
And don't be surprised if you see plenty of pumpkins and fall decorations around town. Woodstock fully embraces the season!
This town does not forget about fall decor
Covered Bridge in Downtown
Billings Farm
Address: 69 Old River Rd, Woodstock, VT 05091
Billings Farm & Museum is a working dairy farm and living history museum just outside downtown Woodstock. It's a great place to get a glimpse into traditional Vermont farm life while enjoying the surrounding scenery.
You can see farm animals, explore the historic buildings and exhibits, and learn how Vermont farming has changed over the years. The farm has been operating since 1871, so there's plenty of history here as well.
I especially love this stop in the fall when the surrounding trees are changing colors.
Sugar Bush Farm
Address: 591 Sugarbush Farm Rd, Woodstock, VT 05091
Sugarbush Farm is a family-owned Vermont farm where you can sample maple syrup and homemade cheese while exploring the beautiful property. There are free samples, a farm store and plenty of Vermont-made products to browse.
It's one of those stops that feels like the Vermont experience I had pictured in my head—maple syrup, rolling hills, farm roads, and fall foliage.
A warning from personal experience: The road leading to the farm is unpaved and can be rough in spots. On one of my visits, I hit a rock and ended up with $1,500 in car repairs, so take your time driving up and watch the road carefully!
Quechee Gorge
Address: 5800 Woodstock Road Hartford, VT 05047 United States
Just a short drive from Woodstock, Quechee Gorge is known as the "Little Grand Canyon of Vermont." At 165 feet deep, it's the deepest gorge in Vermont and one of the area's most popular natural attractions.
You can see the gorge from the bridge along Route 4 or take one of the nearby trails to get a closer look. The main overlook is an easy stop if you're short on time, but I'd recommend getting out of the car and walking around if you have the time.
Browse the Quechee Antique Market
Address: 5573 Woodstock Rd, Quechee, VT 05059
If you like antiques and vintage finds, this is a fun stop to add while you're already in the Quechee area visiting the gorge. The antique mall is housed in a large barn with hundreds of booths, so you never quite know what you're going to find.
It's also a fun place to pick up unique Vermont souvenirs that aren't the typical tourist-shop finds. I got my favorite winter gloves here years and ago and they are still in great condition!
Make sure you continue looking around back to feed some alpacas.
Take a Scenic Drive Through Vermont
Even though driving around might not sound like an activity, I think it's one of the best parts of visiting Vermont in the fall. There's something about driving down a tree-lined road with colorful leaves, open fields, historic farmhouses, and mountains in the distance that makes the trip feel like a movie.
The best part is that you don't really need a plan. Pick a road, turn up your favorite playlist, and enjoy the scenery.
A few roads and areas to explore around Woodstock include:
Old River Road
Cloudland Road
Galaxy Hill Road
Old Stage Road
Route 4
Give yourself some unplanned time during your trip. Some of my favorite Vermont moments have come from simply driving around and stopping whenever something caught my eye.
How Long Do You Need in Woodstock?
I recommend spending at least one full day in Woodstock, especially if you're visiting during the fall. That gives you enough time to explore downtown, visit a farm, see the covered bridges, and take a scenic drive without feeling rushed.
If you have two days, even better. You can slow down, spend more time hiking or exploring the surrounding towns, and enjoy some of Woodstock's restaurants and shops.
If you're visiting during peak fall foliage, I'd personally make Woodstock part of a longer Vermont road trip rather than trying to squeeze everything into a few hours.
More Vermont Travel
If you're planning a longer Vermont fall trip, I'd also recommend spending a weekend in Burlington. It's a completely different experience from Woodstock, with Lake Champlain views, breweries, restaurants, and easy access to Stowe and Waterbury.
I recently put together a guide to my own fall weekend in Burlington, including where we stayed, what we ate, and the places we explored.