Named the prettiest town in America, Woodstock, VT, holds a myriad of exciting and insightful activities — in fact, when you prioritize the best things to do in Woodstock, Vermont in the fall, it’s even more magical! There are quaint restaurants, boutique stores, and surrounding natural wonders to delight even the most weary traveler.
And hint hint, it’s one of my favorite places to visit in the fall — you’ll see why soon!
This ideal New England village has outdoor activities, architectural attractions, and plenty of small hidden gems to discover. If you’re taking a trip but are unsure of what to do in Woodstock, VT in fall this list covers everything you need to know.
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Why Visit Woodstock, VT in Fall?
It would be easier to list the reasons not to visit Woodstock.
I mean, it’s the perfect additional to a fall weekend in Vermont!
If you’re looking for that Hallmark-style town with friendly locals and charming stores scattered throughout, this is the place.
Woodstock is known for its beauty, and it’s a firm favorite for those traveling during the festive holidays.
The village is also one of the great places you can stop at while doing a (highly recommended) New England fall road trip.
It works as a day trip or even an overnight stop, whatever fits into your schedule.
Top Woodstock, VT, Things to Do in the Fall
Charming and welcoming, with 19th-century architecture and well-preserved history, Woodstock is packed with places to go and things to see.
Live out your small Americana town fantasy while spending some time in the town of Woodstock, VT.
Next Read: Continue the New England fun and read about visiting Stowe in the fall!
#1 Check Out Downtown Woodstock, Vermont
Downtown is made up of Central, Elm, North Park, and South Park Streets.
Here you will find a number of small businesses, each as unique as the next.
There are plenty of places to pop in for a quick bite or do some shopping for souvenirs!
This is a great time to discover the town’s many boutique stores, coffee shops, and general atmosphere.
You don’t need a plan here, just follow the shop windows and let your feet guide you to where you need to be.
The town has a gorgeous library and a handful of charming bookstores to browse through.
You can also take a walk down one of the many side streets and explore all that Woodstock has to offer.
Next Read: Visiting Acadia National Park in the fall
#2 Stop by the Billings Farm and Museum
This is a great activity, and there’s something for the whole family.
The outdoor history museum is also a fully operational dairy farm.
There are prize-winning Jersey cows, Southdown sheep, and more farm animals that you can pet and admire.
The farm has a daily schedule for anyone wanting to visit to check out.
You can pop into the gift shop, check out an art exhibit, take a class in preserving food, attend a watercolor workshop, and go for a wagon ride around the farm.
#3 Visit the Marsh-Billings-Rockefeller National Historical Park
This park is home to the Marsh-Billings-Rockefeller Mansion, which you can visit and take a self-guided tour through.
And don’t miss out on a stroll through the beautiful gardens.
But the park also has an abundance of outdoor activities for the whole family.
This park, like most of the area, is best seen during autumn, but if that’s not possible, all is not lost.
There are hiking trails to walk, horse riding tours, and winter sports on offer.
Next Read: Things to do in New York’s Adirondacks in Fall
#4 Sample Some Maple Syrup
Vermont is known for its maple syrup, so it would be a shame to visit and not try some.
Stop by one of the many sugar shacks located around Woodstock and get a taste of this Vermont staple.
There are several maple farms dotted around the outlying areas of the town.
Each one offers its own unique style of maple syrup that you can try and then buy to take home.
#5 Sleepy Hollow Farm
Take a drive through the woods and go to the famous Sleepy Hollow farm!
This is a must-do activity in the fall.
The farm was originally opened in the late 1780s by two brothers from Connecticut.
And today it’s a photography hot-spot in Vermont!
Next Read: Things to do in Stowe, Vermont
#6 Take a Hike
There are plenty of hiking trails located around Woodstock, so you simply must get out and explore!
Whether you’re looking for a short hike or something more challenging, you’ll be sure to find a trail that suits your needs.
Be sure to ask a local or check out local maps before you leave.
Some trails (like The Appalachian Trail) are more suitable for experienced hikers.
But others (like the Eshqua Bog Natural Area) are perfectly accessible to all fitness levels.
This definitely has to be on your list for the fall!
Next Read: Visiting New Hampshire White Mountains in fall
#7 Go Tubing at the Quechee Gorge
The Quechee Gorge is one of Vermont’s most popular attractions.
Located just outside of Woodstock, the gorge is a great place to go tubing in the summer months.
You can rent a tube from one of the many outfitters in town and float down the river.
It’s a great way to relax and take in the scenery.
Even if you don’t want to get on the water, the Quechee Gorge is still worth a visit.
The scenic nature views are breathtaking, and there are plenty of hiking trails.
#8 Attend a Woodstock Farmers Market
Woodstock is home to a number of farmer’s markets, so be sure to check one out during your visit.
You’ll find fresh produce, local crafts, and live music at most markets.
Markets are typically held on Saturdays from May to October.
The best market is undoubtedly the Woodstock Farmers Market.
This market has a little bit of everything, from local produce to handmade goods. You’ll definitely find something that catches your eye.
#9 Visit the Woodstock History Center
Since World War II, the Woodstock History Society has been working hard to preserve this town’s past and make sure that it’s there for future generations to learn from.
The center is home to a number of exhibits, including one on the history of the Marsh-Billings-Rockefeller National Historical Park.
#10 Stop at Sugarbush Farm
Sugarbush Farm is a working farm located just outside of Woodstock.
The farm offers a variety of activities, including hayrides, animal petting, and maple sugaring demonstrations.
It’s a well-known attraction in the area and proves to be one of the top things to do in Woodstock, Vermont.
Take a walk through the maple trees to see where the syrup comes from, watch how the farm’s locally-made cheese is packaged, and say hello to all of the farm animals.
#11 Go Skiing or Snowboarding at Suicide Six
If you’re visiting Woodstock in the winter months, be sure to hit the slopes at Saskadena Six — previously named Suicide Six.
Don’t let the name scare you off! This ski resort offers a variety of trails for all skill levels.
It’s been open to the public for 86 years and continues to be a favorite for all who visit.
There are 24 trails and slopes, ranging from beginner to intermediate and advanced.
The ski lift operates from 9 am to 4 pm, Wednesday – Sunday.
From the town center, the slopes are less than a 10-minute drive.
So it’s easily accessible and you won’t have to spend too much of your time traveling.
#12 Stroll Through the Kelly Way Gardens
The Woodstock Inn and Resort is home to quite a bit of Woodstock’s attractiveness, but their master gardener Benjamin Pauly really helps bring the natural beauty to life.
You can find his work at the Sunflower House at Billings Farm & Museum and at The Gourdwalk in Kelly Way Gardens.
The gardens offer more than just beauty to enjoy, they hold the source of the Woodstock Inn & Resort’s hearty meals.
The inn has a farm-to-table program using the garden’s produce to feed its guests.
This provides the inn and everyone who is lucky enough to stay there with an on-site holistic food supply.
#13 Snap a Picture of the Covered Bridges
Put your camera gear to good use while visiting this town and take a few photos of the covered bridges.
There are four of these you should see, all of which have been standing for over a century.
These bridges are now popular tourist attractions and make for some great pictures.
The most photographed bridge is the Taftsville Bridge, which was built in 1836 and spans the Ottauquechee River.
It’s one of the oldest covered bridges in the country and is truly a sight to behold.
There is also Lincoln Covered Bridge, Middle Covered Bridge, and Quechee Covered Bridge that you can find throughout the town.
#14 Get Outside
In between finding all of the top Woodstock things to do and the historical attractions and landmarks, take some time out to soak up the sun.
The town has ample opportunities to get outside and enjoy the stunning natural surroundings.
You can spend a few hours biking, swimming, golfing, or enjoying one of the many water sports on offer.
If you’re visiting in the warmer months, these are great alternatives to skiing down the snowy slopes.
#15 Work Your Way Through the Food Scene
Besides maple syrup and cheese, Woodstock has a host of other delicious foods to try.
Get an ice cream from White Cottage Snack Bar, a drink and dinner from Worthy Kitchen, or a coffee breakfast from Mon Vert Cafe.
And if you’re able, you really should try to book a seat at the Woodstock Inn’s Red Barn Dinner Series.
Here you’ll be introduced to local produce and artisan foods and treated to a scrumptious meal.
#16 Admire the Birds at New England Falconry
Found at Woodstock Inn & Resort, New England Falconry offers guests the chance to meet some of the falcons in their care.
There are sessions offered that give you insight into these birds of prey and their history.
You can also see them take flight in what is an amazing spectacle of power and grace.
Where to Stay While Visiting Woodstock, VT
Whether you need a simple spot to spend the night, or a cozy home-away-from-home for an extended trip, Woodstock has no shortage of places to stay. Take full advantage of that well-known Vermont hospitality and book into one of the following accommodations.
Charming and Chic Vacation Rental ($$) — This little 2-level apartment has been named perfectly. It really is a charming and chic rental, adjacent to Tribou Park and within walking distance of numerous shops and restaurants. Check availability and prices
Delightful Cozy Space in Woodstock Village ($$) — The apartment is private and furnished with everything you’d need for the perfect vacation. It’s set in a green and leafy area but is still close to many of the things to see in Woodstock, VT. Check availability and prices
It’s Foliage Season! ($$) — If you’re in New England for the fall foliage, this is the best place to stay. The simple yet homely log cabin is perfectly located, and the hosts really do know their town inside and out. Check availability and prices
Ready to See the Best Woodstock, Vermont Attractions?
Woodstock, VT, is the perfect place to get away from it all and enjoy some time in nature.
With plenty of things to do, you’ll never find yourself bored. So pack your bags and head to Woodstock for a Vermont vacation you’ll never forget.
There are plenty of other places to explore and things to do in Woodstock, Vermont.
These are just a few top favorites.
Whether you’re visiting for the fall foliage or any other time of year, you’re sure to find plenty to keep you busy in this charming little town.
If you’re looking for more charming Vermont destinations, why not consider visiting Stowe in the Fall?
