With crisp temperatures, the crunch of leaves underfoot, and outstanding autumnal decor, meandering through the quaint town of Woodstock, Vermont, will likely be a highlight of your Fall trip to Vermont. Seeing Woodstock, Vermont, in Fall is an incredible experience. It has everything you could want from a festive Fall getaway in New England.
The town of Woodstock comes to life with vibrant Fall foliage, and many of the residents even go the extra mile to decorate their homes elegantly with pumpkins and mums. When you’re not strolling through town, you’ll be seeking out the best Fall foliage, farm hopping, and indulging in maple creemees.
This is such a cute town that you will be planning your next trip back after one Fall getaway to Woodstock, VT.
Before You Go
🏨 Book Woodstock Inn and Resort, an iconic luxury hotel located in the village! Or enjoy a stay at a quintessential New England hotel located along the Quechee River, The Shire Woodstock! Hotels sell out well in advance during the Fall, so book your hotel ASAP!
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🚗 Rent a Car: You’ll need a car to explore Vermont. Check out the best rental car prices here.
Disclaimer: This article contains affiliate links. I may earn a small commission when you purchase a product or book a stay through these links at no extra cost to you.
Table of Contents
Woodstock Vermont Fall Foliage- When is Peak Fall Foliage in Woodstock, VT?
Peak fall foliage in Woodstock typically lands from the last week of September to early October. However, it can vary depending on the year. The Vermont Foliage Forecaster is an excellent tool to estimate when you’ll find the best colors in Woodstock.
If you plan on visiting the second or third week of October, you should see some great foliage. Looking at the peak for the prior year can usually help you determine the best time to visit.
Woodstock VT Peak Foliage 2024
It’s still a bit early to tell what the peak dates for Woodstock Vermont foliage will be. Yet, it will likely land the first week of October based on previous years.
Things to do in Woodstock, Vermont in Fall
This list of best things to do in Woodstock, VT in Fall includes the best spots to see Fall foliage and festival Fall activities. Many of these activities can be done year-round, yet they are especially worthwhile when visiting Woodstock in the Fall. This list also includes some things to do in Quechee, Vermont in Fall. The town is nearby Woodstock and is easy to include during your trip to Woodstock.
Explore the Town of Woodstock
The town of Woodstock is so charming. During the Fall months, many Inns, shops, and houses in Woodstock are decorated with autumnal decor. You’ll find cute pumpkin displays around town and stunning Fall foliage that make the Woodstock, Vermont village even more picturesque.
With so many trees lining the roads in Woodstock, the entire town is perfect for a leaf-peeping stroll. If you want to see the best Fall photo spots in Woodstock, those are highlighted later in this guide.
Get Maple Syrup at Sugarbush Farm
Sugarbush Farm is a maple farm near Woodstock and is a great spot to visit in the Fall. What better way to spend some time in Vermont in Fall than a scenic drive to a farm selling maple syrup cheese? I’m not quite sure if anything could be more Vermont than that.
Before browsing the shop, don’t miss the maple syrup and cheese samples. Sampling will help you decide which bottle of syrup to bring home! At Sugarbush Farm, you can take a self-guided tour through the maple house and stroll through the maple trees to a quaint chapel in the woods.
READ MORE: Visiting Sugarbush Farm in Woodstock VT
Take Photos of Sleepy Hollow Farm
Sleepy Hollow Farm is a picturesque farm outside of Woodstock. During the Fall, tourists and photographers flock to this farm to see the stunning Fall foliage. From the road, this farm is stunning, with its long driveway and vibrant trees in the background. Stopping at Sleepy Hollow Farm is one of the top things to do in Woodstock, VT, in the Fall.
Keep in mind that this is a residential farm. Keep off their property. You can get a gorgeous photo from the road, so there is no need to violate their privacy.
2024 Update: From September 23 to October 15, 2023, this road was closed to non-residents due to the overwhelming influx of tourists visiting this farm. I will watch the news to see if it will again be closed for the 2024 Fall foliage season.
Address: 3429 Cloudland Road, Woodstock, VT 05091
Get a Maple Creemee at Woodstock Scoops
While on a Fall trip to Woodstock, Vermont, you must indulge in a Maple Creemee. A maple creemee is maple-flavored soft-served ice cream (Vermonters call soft-served ice cream creemees, which I think is the cutest thing in the world). Woodstock Scoops is the best spot to grab one of these Vermont treats. This ice cream shop is located in the village of Woodstock and is a great spot to stop for a treat while walking around.
Visit Billings Farm & Museum
Billings Farm is a working farm and outdoor museum that is a fun place to visit on a Fall trip to Woodstock. Visiting Billings Farm & Museum gives you an idea of what life is like on a farm in the Fall months in Vermont.
While at Billings Farm, you will have the opportunity to see a fully-operational Jersey dairy farm, see animals and see demonstrations of cheese making. They even have apple cider donuts available in the Fall.
Price: $19 for adults, $12 for kids (4-15), and Free for kids 3 and under
Address: 69 Old River Rd, Woodstock, VT 05091
Visit the Covered Bridges
Visiting the bridges in Woodstock is such a fun thing to do during your Fall trip. There are more than 100 covered bridges in Vermont, so it is no surprise that visiting these bridges is popular in the state. These bridges are often in scenic locations, which makes them even more picturesque with Fall Foliage. Some of the top bridges to see in Woodstock are Lincoln Covered Bridge, Middle Covered Bridge, Taftsville Covered Bridge, and Quechee Covered Bridge.
Walk Along the Treetops
There is a forest canopy walk at The Vermont Institute of Natural Science in Quechee. This canopy walk allows you to walk along the treetops and is a unique way to experience the stunning Fall foliage. Vermont has some of the best Fall foliage in the world, and this is truly one of the best ways to experience it.
The Vermont Institute of Natural Science is an underrated spot that it seems not many people know about. I was surprised that there weren’t many people at the forest canopy walk, especially during peak foliage. Be sure to add this to your list of places you must visit if you are visiting Woodstock, Vermont, in the Fall.
Price: $19.50 for adults, $16.50 for kids (4-17), and Free for kids 3 and under
Address: 149 Natures Wy, Quechee, VT 05059
Shop at Woodstock Farmers Market
The Woodstock Farmers Market is a great spot for local Vermont goods year-round. And in the Fall months, you can pick up fun-festive things such as Maple-syrup, mums, and pumpkins. This was a great spot to stop for a quick bit to eat to bring on scenic Fall drives near Woodstock. P.S. Woodstock Farmers Market has the most adorable Fall-themed sugar cookies that are delicious.
Hike the Quechee Gorge
Quechee Gorge is one of the most scenic spots to see Fall foliage near Woodstock, Vermont. This gorge, known as “Vermont’s Little Grand Canyon,” is located in the neighboring town of Quechee and offers a scenic and easy hiking trail. You can hike the 2.7-miles trail that follows the gorge or view the gorge from above via the bridge.
Get a Maple Latte at Mon Vert Cafe
A trip to Vermont should include indulging in maple-flavored everything, including coffee. Perhaps it is just the coffee-lover in me, but I think a maple latte is a daily staple on a Fall trip to Vermont. And Mon Vert Cafe in Woodstock is the perfect place for your maple-flavored caffeine fix. Mon Vert Cafe has a wide array of beverages and pastries and is the ideal spot to start your day.
P.S. This cafe gets very busy! If you want a coffee or breakfast, I suggest arriving early. We waiting in line for almost 20 minutes one morning before opting to grab a gas station breakfast because it was taking too long.
Fall Photo Spots in Woodstock, Vermont
In the last section, I mentioned how charming the village of Woodstock is. In this section, we will dive into where to find the best autumnal decor and Fall photo spots in the town of Woodstock, Vermont. There are so many picture-perfect spots in Woodstock! You’ll likely wander past a lot of these spots while exploring town, but if you want to ensure you get some great photos, I’ve got you covered!
Woodstock Inn
Woodstock Inn is a quintessential New England Inn and is incredibly charming in the Fall. The inn is beautifully decorated with pumpkins and dozens of mums near the entry. The flowers frame Woodstock Inn and create a great spot to take Fall photos in Woodstock.
Woodstock Inn is one of the most popular photo spots in Woodstock. Chances are, you will not be the only person trying to take photos here. Try to arrive early to get pictures before it gets too busy, and have patience if you need to wait for others to finish taking their pictures.
The Ardmore Inn
The Ardmore is another charming inn located in Woodstock, Vermont. This Inn does a cute autumnal display facing Pleasent Street at the property’s entrance. There are mums in shades of orange lining the walkway and piles of pumpkins on the steps. It is really cute.
All information I found online says that the Ardmore Inn has been closed for the last two years. However, even though there was no booking information online, the inn was still decorated last year.
General Lyman Mower House
This historic home was built on the site of the first county courthouse in Woodstock, Vermont. Architecturally, it is stunning. And a vibrant red tree is in front of the property, making a lovely photo opportunity in the Fall.
There is a small park across the street from this house. You’ll want to take photos from across the street to get the house and tree in your photo completely.
587 Old River Road
This section of Old River Road is gorgeous, with white fencing and orange and gold-hued foliage. It’s a great spot to allow the foliage to shine in photos, rather than the albeit adorable town of Woodstock.
The property spans a large portion of Old River Road, so there are plenty of spots to choose from to take photos of. Just look for a space with the most leaves still on the branches.
Middle Covered Bridge
Middle Covered Bridge is located within the village of Woodstock and is a very “Vermont” photo op. Seriously, you cannot visit Vermont without seeing at least one covered bridge (or a dozen).
You have to get a little creative with the angle you shoot from to showcase some of the surrounding foliage, but the photos will surely turn out really cute.
11 the Green
This house is located next to Middle Covered Bridge and is so charming. The house is decorated with pumpkins lining the walkway, and various trees behind the home make it extremely picturesque.
16 Pleasant Street
This white house with a white picket fence is a simple yet stunning spot to take Fall photos in Woodstock, VT. The owner of this residential property places tinny pumpkins on all the fence stakes.
If you take a photo from an angle, you can see all the little pumpkins lining the fence.
The Laundry Room
Yes, The Laundry Room is, in fact, a laundromat. And it is the cutest laundromat ever. The Laundry Room, located on Pleasant Street, has fantastic decor in the Fall. The display includes vibrant orange pumpkins, Fall wreaths, and flowers.
First Impressions Salon & Spa
The red brick exterior of this salon is the perfect backdrop for the seasonal Fall decor. The front steps have a cute autumnal display and are a great spot to take Fall photos in Woodstock, Vermont.
Where to Stay in Woodstock, VT in Fall
Here are a few of my top recommendations for where to stay in Woodstock, Vermont. Remember that accommodations are likely to sell out during October. If you are already planning your trip, that means everyone is starting to plan their trips. Book ASAP to ensure you have a good place to stay.
TRAVEL TIP: Hotels sell out so far in advance during the Fall foliage season in Vermont. If you’re unsure the exact dates of your trip, I recommend booking two separate weeks for your trip now (most properties on Booking.com have free cancellation.) You can cancel the dates you won’t be traveling later. But at least you’ll know you have somewhere to stay. Trust me, when I planned a trip to Vermont, almost the entire state was sold out about by September.
Woodstock Inn & Resort
The Woodstock Inn & Resort is the most iconic place to stay in Woodstock. This inn exudes quaint New England luxury. The rooms are spacious and elegant, and the location is prime. Staying at Woodstock Inn is a bit of a splurge, but it is worth every penny if it is within your budget.
Check rates:Booking.com | Read reviews: Trip Advisor
The Vesper
The Vesper Woodstock is a modern bed and breakfast located just in the town of Woodstock. This property is very small and offers a limited number of rooms. Book fast if you want to secure a room here.
Check rates:Booking.com | Read reviews: Trip Advisor
The Shire Woodstock
The Shire Woodstock is situated along the Ottauquechee River and offers beautiful river views from the rooms. While the scenic views make this property feel a bit more secluded, it is still within a few minutes walk to the center of town.
Check rates: Booking.com | Read reviews: Trip Advisor
Fall in Woodstock, Vermont: Wrap-up
Woodstock is one of the best places to experience Fall in Vermont. There is so much to do in Woodstock, especially during the Fall season; whether you are meandering the town of Woodstock for seasonal decor or checking out some of the best things to do in the area, you will surely have an incredible time with a Fall getaway to Woodstock. Woodstock is the type of town that will pull at your heartstrings and beckon you to plan a return trip after your first visit.
For more travel inspiration, check out these posts:
🍁 Sugarbush Farm Guide: The Best Maple Syrup Farm in Woodstock
🚠 Experiencing Fall in Stowe Vermont | 10 Festive Things to Do
🥾 10+ Perfect Things to Do in Quechee Vermont for the Perfect Getaway
For more New York travel, check out my Vermont section!
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This article was originally published Aug 31, 2022, yet has been updated.