Welcome to the best things to do in Woodstock, Vermont in the fall!
Fall is arguably the most beautiful season in Woodstock, Vermont.
The small town’s rolling hillsides burst into vibrant hues of red, orange, and yellow, making it a prime destination for leaf-peepers.
But there’s more to do in Woodstock than just admire the fall foliage.
From apple picking to scenic drives and cozy fireside dinners, this charming town offers countless activities to make the most out of your autumn travels.
In this blog post, I’ll share my top picks for the best things to do in Woodstock during the fall season.
This list will help you experience all that this picturesque New England town has to offer during one of its most magical seasons.
So grab your sweater, and get ready to explore!
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Woodstock Essentials
Where To Stay In Woodstock
How To Get Around Woodstock
Make sure to reserve your rental car in advance on RentalCars.com.
1. Explore Downtown Woodstock
Exploring downtown Woodstock is a must-do activity for anyone visiting this charming New England town, especially during the fall season.
The streets are lined with quaint shops and boutiques, offering everything from handmade crafts to locally sourced produce.
One of the most popular shops in the area is Vermont Flannel, where you can find cozy flannel shirts and blankets that are perfect for chilly autumn days.
Another great spot is Clover Gift Shop, which offers a wide range of unique gifts and souvenirs that capture the essence of Woodstock.
And if you’re looking to stock up on home goods, Woody’s Mercantile has everything you need.
Book lovers should head to Yankee Bookshop, the oldest continuously operated independent bookshop in the United States.
No matter what your interests are, exploring downtown Woodstock is sure to be one of the highlights of your fall visit to Vermont.
2. Admire Middle Covered Bridge
The Middle Covered Bridge is a must-visit spot in Woodstock during the fall season!
This iconic bridge spans across the Ottauquechee River and offers breathtaking views of the surrounding foliage.
Located right across from the village green, it’s a perfect spot for taking photos, or enjoying a leisurely stroll.
Plus, it’s one of Vermont’s oldest covered bridges, so history buffs will definitely appreciate its unique design and construction.
If you visit on a sunny day, you might even catch a glimpse of the river reflecting the vibrant autumn colors.
So grab your camera, and head over to Middle Covered Bridge for an unforgettable fall experience in Woodstock.
Related: Vermont Quotes, Captions & Puns
3. Have lunch at Mon Vert Cafe
If you’re looking for a cozy and delicious dining experience in Woodstock during the fall season, Mon Vert Cafe is one of the best restaurants to check out.
Right in the heart of downtown, this charming cafe offers a warm and welcoming atmosphere, complete with rustic decor and a roaring fireplace.
It’s the perfect place to pop inside on a chilly autumn day.
And when it comes to food, Mon Vert Cafe does not disappoint.
Their menu features an array of mouth-watering dishes made with locally-sourced ingredients, including hearty soups, flavorful sandwiches, and freshly-baked pastries.
Plus, they offer a variety of hot drinks like coffee and tea that are sure to warm you up from the inside out.
Whether you’re looking for a quick bite or a leisurely lunch, Mon Vert Cafe is the perfect spot to enjoy some good food and cozy vibes this fall season.
4. Take a picture at the pumpkin fence
One of the most iconic spots in Woodstock, Vermont during the fall season is the pumpkin fence.
Located at 16 Pleasant Street, this charming fence is lined with a photogenic array of pumpkins, making for a picture-perfect autumnal scene.
Taking a photo at the pumpkin fence has become somewhat of a tradition for visitors to Woodstock during this time of year, and it’s easy to see why.
Not only does it make for a great Instagram post, but it also captures the essence of fall in New England perfectly.
So if you’re looking for one of the best photo spots in Woodstock this fall, head here.
Just make sure to be respectful, because this is a private home.
5. Visit Sugarbush Farm
If you’re looking for an authentic taste of Vermont during the fall season, a visit to Sugarbush Farm is an absolute must.
This family-owned farm has been producing award-winning cheese and maple syrup for over 75 years, and you can experience the magic firsthand.
Take a stroll through the scenic grounds, which are especially picturesque during the autumn months when the foliage is at its peak.
The short nature trails winds through the sugarbush, and past a charming chapel in the woods.
You can also take a tour of the sugarhouse and learn about the maple syrup-making process, or sample cheese in the farm store.
Make sure to take home some local maple syrup or other souvenirs from their gift shop.
You’ll even catch a glimpse of their adorable farm animals, including cows, goats, and sheep.
So if you’re looking for a fun and educational activity that celebrates all things Vermont this fall season, be sure to add Sugarbush Farm to your list.
6. Hike the Quechee Gorge Trail
If you’re an outdoor lover visiting Woodstock in the fall, hiking the Quechee Gorge Trail is a must-do activity.
Located in Quechee State Park, this scenic trail follows the rim of Vermont’s deepest gorge and offers stunning views.
The trail is relatively easy, making it accessible for hikers of all skill levels, and takes roughly 30 minutes to complete.
Along the way, you’ll have plenty of opportunities to stop and take in the breathtaking scenery or snap some photos to capture your memories.
And if you’re up for a longer hike, there are several miles of trails that extend into the surrounding woods.
So whether you’re looking for a quick nature walk or an all-day adventure, hiking the Quechee Gorge Trail is one of Woodstock’s best fall activities that shouldn’t be missed.
7. Sleepy Hollow Farm (please read below)
2024 UPDATE
This Instagram-famous farm has been featured in countless photos, magazines, and social media posts over the years.
While I (and many others) used to recommend it as a beautiful photography destination, I no longer recommend visiting Sleepy Hollow Farm.
Unfortunately, overtourism has hit the area hard, impacting the local residents.
Due to the their frustration, the local government has actually started shutting down the road to tourists during peak fall season.
So instead of visiting Sleepy Hollow Farm, please visit one of the other farms on this list!
8. Hike to the top of Mount Tom
If you love a good hike and breathtaking views, hiking to the top of Mount Tom is one of the best things to do in Woodstock, Vermont during the fall season.
The trail is located just minutes from downtown Woodstock and offers a moderate climb that takes roughly 1-2 hours to complete.
Along the way, you’ll enjoy stunning views of the surrounding foliage and can take a break at several scenic overlooks along the trail.
Once at the summit, you’ll be rewarded with panoramic views of Woodstock and the surrounding mountains that are simply awe-inspiring.
Whether you’re an experienced hiker or just looking for a fun outdoor activity, hiking to the top of Mount Tom is sure to be a highlight of your visit to Woodstock in the fall.
9. Try a Vermont Maple Creemee
No visit to Woodstock, Vermont during the fall season is complete without trying a Vermont Maple Creemee.
This delicious treat is a local favorite!
A “creemee” is basically a soft-serve ice cream that’s creamy, sweet, and delicious.
The addition of maple syrup gives it a unique flavor that’s distinctly Vermont.
One of the best spots to try a maple creemee is at Woodstock Scoops, located right in the town center.
Your taste buds will thank you!
10. Visit Billings Farm & Museum
If you’re looking for a fun and educational activity to do in Woodstock, Vermont during the fall season, look no further than Billings Farm & Museum.
This working dairy farm and museum offers the chance to learn about Vermont’s agricultural history and its modern-day farming practices.
You can explore the farm’s exhibits, watch live demonstrations, and even pet some of the farm’s resident animals, like Jersey cows and horses.
During the fall season, you can also enjoy special events like pumpkin carving, cider pressing, and other seasonal activities.
Plus, the rolling landscape makes this one of the best places to enjoy fall foliage in Woodstock.
With something for visitors of all ages to enjoy, Billings Farm & Museum is one of the best things to do in Woodstock.
11. Admire the historic homes
After you finish exploring downtown, head to Woodstock Village to admire the beautiful historic homes.
The town’s charming architecture and fall foliage create a picturesque setting that’s straight out of a postcard.
Many of the homes in Woodstock date back to the 19th century and are well-preserved, offering a glimpse into the town’s rich history.
Whether you’re an architecture enthusiast or simply looking for a leisurely way to enjoy the fall colors, admiring the historic homes in Woodstock Village is an unmissable activity.
12. Have dinner at Cloudland Farm Restaurant
Located on the working Cloudland Farm, the Cloudland Farm Restaurant serves dishes made with fresh, locally sourced ingredients.
Farm-to-table philosophy is at the heart of their culinary approach, with a focus on using seasonal produce and sustainable farming practices.
The dining experience is enhanced by the stunning views of the surrounding countryside, which provide a serene and peaceful backdrop for enjoying a meal.
Whether you’re looking for a romantic dinner for two or a gathering with friends and family, dining at Cloudland Farm is an unforgettable experience that celebrates the best of Vermont’s food culture.
13. Visit Taftsville Covered Bridge
No trip to Woodstock, Vermont is complete without a visit to the Taftsville Covered Bridge, especially during the fall season.
This iconic covered bridge spans over the Ottauquechee River and offers beautiful views of the surrounding autumn foliage.
Built in 1836, it’s one of the oldest covered bridges in Vermont and is listed on the National Register of Historic Places.
You can take a leisurely stroll across the bridge or simply admire its picturesque beauty from afar.
The area around the bridge also offers several hiking trails and picnic spots, making it a perfect fall outing.
With its charming architecture and breathtaking scenery, Taftsville Covered Bridge is truly one of the best things to do in Woodstock during the fall season.
14. Explore Marsh-Billings-Rockefeller National Historical Park
If you’re looking for a fun experience in Woodstock, Vermont during the fall season, look no further than Marsh-Billings-Rockefeller National Historical Park.
This park is not only a beautiful natural area with stunning views of the surrounding forest, but also a living museum of conservation history.
You can take guided tours of the historic mansion and gardens, which were once owned by three generations of conservationists: George Perkins Marsh, Frederick Billings, and Laurance Rockefeller.
The park also offers several hiking trails that provide access to beautiful scenic vistas and prime leaf-peeping opportunities during the autumn months.
With its rich history and natural beauty, Marsh-Billings-Rockefeller National Historical Park is truly one of the best things to do in Woodstock during the fall season for both nature lovers and history buffs alike.
15. Stay at Woodstock Inn & Resort
For a luxurious and relaxing getaway in Woodstock, Vermont during the fall season, staying at the Woodstock Inn & Resort is an absolute must.
This historic inn offers elegant accommodations with traditional New England architecture and décor, as well as modern amenities such as spa services and fine dining options.
The inn’s location in the heart of Woodstock also provides easy access to all of the area’s fall attractions.
With its cozy atmosphere and prime location, the Woodstock Inn & Resort offers something for everyone during the autumn months in Vermont.
Click here to check availability at Woodstock Inn & Resort.
16. Take a day trip to Stowe
Stowe, Vermont is a charming mountain town known for its picturesque New England scenery, stunning views, and vibrant fall foliage.
It’s one of the best day trips from Woodstock, and I highly recommend it!
You can explore the quaint downtown area, which is filled with local shops and restaurants.
Or, take a gondola ride up to the top of Mount Mansfield for panoramic views of the surrounding landscape.
Make sure to fill up on fresh apple cider and apple cider donuts at Cold Hollow Cider Mill.
Stowe also offers several hiking trails that provide access to beautiful waterfalls and other natural attractions.
With its classic Vermont charm and breathtaking autumn scenery, taking a day trip to Stowe is truly one of the best things to do near Woodstock during the fall season.
Related: 25 Best Things To Do In Stowe, Vermont In The Fall
17. Browse Woodstock Farmers Market
If you’re looking to experience the best of Vermont’s fall harvest, a visit to the Woodstock Farmers Market is a must.
This vibrant market offers an array of fresh produce, artisanal cheeses, baked goods, and other locally made products that capture the essence of autumn in New England.
You can browse the stalls and sample seasonal treats while taking in the lively atmosphere and stunning scenery of the surrounding countryside.
The market also hosts live music and other events throughout the season, making it a fun and festive destination.
Whether you’re looking to stock up on farm-fresh ingredients or simply soak up the sights and sounds of fall in Vermont, the Woodstock Farmers Market is definitely one of the best things to do in Woodstock in fall.
18. Take a Forest Canopy Walk
If you’re looking for a unique way to experience the beauty of fall in Vermont, add a canopy walk at the Vermont Institute of Natural Science (VINS) to your list.
This exciting attraction allows you to explore the treetops from a whole new perspective, with suspended bridges and platforms that offer panoramic views of the surrounding forest.
Along the way, you can learn about local wildlife and ecology from knowledgeable guides who share their passion for nature with enthusiasm and expertise.
The canopy walk is especially breathtaking during the fall season when the foliage is at its peak, adding vibrant hues of red, orange, and gold to the already stunning landscape.
It’s also ADA-accessible, making it a great activity for all ages and mobilities.
Whether you’re a nature lover or simply seeking an unforgettable adventure, taking a canopy walk at VINS is definitely one of the best things to do in Woodstock during this magical time of year.
19. Pick apples at Whitman Brook Orchard
When it comes to quintessential fall activities, few things are as beloved as apple picking.
One of the best places to pick apples in Woodstock is at Whitman Brook Orchard.
Located just a short drive from downtown Woodstock, this family-owned orchard boasts over 30 varieties of apples that are available for picking from late August through early November.
You can wander through the picturesque orchard, breathing in the crisp autumn air and admiring the stunning foliage that surrounds them.
Whether you’re looking for juicy heirloom apples for baking or tart cider apples for pressing, you’re sure to find what you’re looking for at Whitman Brook Orchard.
20. Walk the Ottauquechee River Trail
If you’re looking for an easy hike in Woodstock, the Ottauquechee River Trail is a must-do during the fall season.
This picturesque nature trail winds its way through beautiful forests and along the banks of the scenic Ottauquechee River, offering breathtaking views of colorful foliage at every turn.
Along the way, you can take in historic covered bridges and charming New England architecture while enjoying the crisp autumn air.
With so much natural beauty to explore, it’s no wonder why the Ottauquechee River Trail is one of the best things to do in Woodstock during this magical time of year.
21. Try falconry
If you’re looking for a truly unique experience in Woodstock, Vermont during the fall season, consider trying your hand at falconry.
This ancient sport involves working with trained birds of prey to hunt for game in a natural setting, and there’s no better time to try it than during the crisp autumn months.
As the leaves change colors and nature comes alive, you can take part in this age-old tradition while surrounded by stunning scenery and majestic wildlife.
Whether you’re a seasoned pro or a first-time falconer, the experienced guides at New England Falconry will ensure that you have an incredible time while learning about these fascinating creatures.
With its perfect blend of adventure and natural beauty, falconry is one of the most unique things to do in Woodstock during the fall season.
Common Questions
Is Woodstock, VT worth visiting?
Yes! Whether you’re looking for an idyllic weekend getaway or a longer vacation filled with outdoor adventure and small-town New England charm, Woodstock is definitely worth a visit.
Where can I see foliage in Woodstock, VT?
The best places to see fall foliage in Woodstock, Vermont include Mount Tom, Billings Farm & Museum, Quechee Gorge, and scenic drives along Route 4 or River Road.
What is the best time of year to visit Woodstock, VT?
The best time of year to visit Woodstock, Vermont depends on your interests and what you hope to experience!
If you love outdoor activities like hiking, biking, and fishing, the summer months of June through August are ideal.
The warm weather and long days provide ample opportunities for exploring the lush natural beauty of the surrounding area.
In the fall months of September through November, you can witness the breathtaking spectacle of New England’s famous fall foliage as the leaves turn vibrant shades of red, orange, and gold.
Winter enthusiasts will enjoy the snowy wonderland that Woodstock becomes from December through February when skiing, snowshoeing, and ice skating are popular pastimes.
Finally, spring is a great time to visit for those who want to experience Vermont’s maple sugaring season or witness the town come back to life after a quiet winter.
Whenever you choose to visit Woodstock, there’s no doubt that this charming town will capture your heart!
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