10 Best Things to Do in Woodstock, Vermont in the Fall

Figuring out what to do in Woodstock, Vermont in the fall can feel like a dream as this little town is straight out of a postcard when the leaves start turning.

With its covered bridges, historic village streets, and rolling hills covered in fiery foliage, it’s no wonder Woodstock is one of the most popular places to visit in Vermont in autumn.

I’ll walk you through the best things to do in Woodstock in the fall, from iconic photo spots and scenic hikes to cozy farm visits and local markets.

Whether you’re planning a weekend getaway or just passing through on a Vermont road trip, this list has everything you need to make the most of your time in this charming New England town.

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Best Things to Do in Woodstock in the Fall

1. Explore Woodstock Village

The village of Woodstock feels like it was made for fall. Historic brick buildings, tree-lined streets bursting with color, and little shops you’ll want to peek into at every corner. It’s easy to spend a whole afternoon just wandering here!

Start on Central Street and make your way around the village green.

Stop by F.H. Gillingham & Sons, a general store that’s been around since 1886, for Vermont-made products, maple candy, and unique gifts.

If you’re after something cozy, pop into Yankee Bookshop, Vermont’s oldest independent bookstore. For coffee or a light lunch, Mon Vert Café is a local favorite with great sandwiches and fresh baked goods.

The village is very walkable, but wear comfy shoes since you’ll be hopping in and out of shops and exploring side streets.

If you’re visiting in peak foliage season (late September to mid-October) and staying elsewhere, plan to arrive early in the day. Parking fills up fast, especially on weekends!

2. Walk across the Middle Covered Bridge

You can’t visit Woodstock in the fall without crossing the Middle Covered Bridge at least once!

This classic wooden bridge spans the Ottauquechee River and makes for one of the most photographed spots in town, especially with the surrounding trees lit up in autumn colors.

It’s an easy walk from the village green, so you can pair it with a stroll through town. The bridge is open to both cars and pedestrians, but there’s a separate walkway along one side, so you can stop and enjoy the views without worrying about traffic.

Don’t forget to peek out the windows for a perfect river view framed by the wooden beams!

For the best photo ops, visit in the morning or late afternoon when the light is softer. It’s also a great spot to catch reflections of the fall foliage in the water below if the river is calm.

3. Spend an afternoon at Billings Farm & Museum

Just a short walk or drive from the village, Billings Farm & Museum is a must if you want to experience Vermont’s rural charm up close.

This working dairy farm has been around since 1871 and still feels like stepping back in time. In the fall, the scenery here is incredible – rolling fields surrounded by brilliant foliage and grazing Jersey cows make for a picture-perfect setting.

You can tour the restored farmhouse to see how families lived in the 19th century, explore interactive exhibits about Vermont’s farming history, and watch demonstrations like butter churning or sheep shearing (depending on the season).

Outside, don’t miss the chance to meet the resident animals, including draft horses, sheep, and chickens. We even saw some baby cows, and they were super cute!

There’s also a small café on-site where you can grab a warm drink or a snack. If you’re visiting in October, check their schedule for special fall events like wagon rides and harvest festivals.

Plan to spend at least 2-3 hours here, and wear layers – it can get breezy out in the fields.

4. Hike to the top of Mount Tom

For one of the best views of Woodstock draped in fall colors, head up Mount Tom. The summit overlooks the entire village and the surrounding hillsides, which glow with reds, oranges, and yellows in peak foliage season.

It’s part of Marsh-Billings-Rockefeller National Historical Park, and there are several trails to choose from depending on how much time and energy you have.

The most popular route is the Faulkner Trail, which starts right in the village near Faulkner Park. It’s about 2.5 miles round trip and climbs steadily with a series of switchbacks, making it manageable for most people.

The trail is well-maintained, but it can be a little muddy in the fall, so sturdy shoes are a good idea. At the top, you’ll find a stone bench where you can catch your breath and take in the incredible panoramic view.

If you prefer a gentler option, the carriage roads on the other side of Mount Tom are wider and less steep, perfect for a longer but easier loop. Either way, it’s worth setting aside a couple of hours for this hike – you won’t regret it!

5. Snap some photos at Sleepy Hollow Farm or Jenne Road Farm

Sleepy Hollow Farm has become one of Vermont’s most famous photo spots, and it’s easy to see why.

The winding dirt road, rustic red barn, and rolling hills covered in golden leaves look like something out of a postcard. It’s especially magical early in the morning when the fog hangs low over the fields!

But in recent years, road access has been restricted during peak foliage season because of the huge crowds flocking here. Only local residents and their guests are allowed to drive in during the busiest weeks of fall.

If you’re hoping to visit, check in advance to see if the restrictions are in place, and always be respectful of private property – this is still someone’s home!

For an alternative, Jenne Road Farm in Reading is just as stunning and doesn’t have any access issues. It’s a quieter spot with a classic Vermont barn and sweeping countryside views that light up with fall colors.

6. Admire the views from Quechee Gorge

Known as Vermont’s “Little Grand Canyon,” Quechee Gorge is one of the most dramatic natural sights near Woodstock.

The Ottauquechee River has carved out this 165-foot-deep gorge, and in the fall, the surrounding trees burst into brilliant reds, oranges, and yellows, making the views even more spectacular.

You can admire the gorge from the bridge on Route 4, which has sidewalks on both sides for pedestrians

 It’s a quick stop if you’re driving through, but if you have more time, take the trail that leads down to the bottom of the gorge. The hike is about 1.5 miles round trip and gives you a whole new perspective from the riverbank looking up at the towering walls.

There’s also a visitor center nearby with restrooms, a small gift shop, and plenty of parking.

7. Stop by Taftsville Covered Bridge

Stopping at Taftsville Covered Bridge is one of the best things to do in Woodstock if you’re chasing those classic Vermont fall views.

Just a few minutes from the village, this historic bridge dates back to 1836 and is one of the oldest in the state. Its bright red exterior stands out beautifully against the autumn foliage, making it a favorite for photographers.

You can drive across the bridge or park nearby to take a closer look. The Ottauquechee River flows underneath, and if you wander down to the water’s edge, you’ll get some lovely angles with the bridge framed by colorful trees.

Since it’s so close to both Sugarbush Farm and Quechee Gorge, it’s an easy stop to add to your Vermont fall itinerary.

8. Take a scenic drive to nearby towns and covered bridges

One of the best things to do in Woodstock in the fall is to explore the charming villages and historic covered bridges scattered throughout the surrounding countryside. These scenic drives are packed with rolling hills, vibrant foliage, and plenty of classic Vermont photo ops.

Start with a quick trip to Quechee, where you can pair a stop at the gorge with a wander through the village and a visit to Simon Pearce to watch glassblowing.

Then make your way to Barnard, a peaceful little spot where you can relax by Silver Lake at Silver Lake State Park or grab a sandwich at the Barnard General Store.

For a longer adventure, head down to Manchester, one of the most beautiful small towns in the state.

Stroll through its boutique shops and tree-lined streets, then visit Hildene, the Lincoln Family Home. This historic estate is stunning in the fall, with its formal gardens and mountain views surrounded by autumn color.

Manchester is also a perfect stop if you’re planning to explore more of the charming small towns in Vermont.

Don’t forget to slow down for covered bridges along the way, like Lincoln Covered Bridge and Mill Covered Bridge, both of which are especially photogenic against a backdrop of fiery leaves.

9. Taste cheese and maple syrup at Sugarbush Farm

No trip to Woodstock is complete without sampling Vermont’s famous cheese and maple syrup, and Sugarbush Farm is the perfect place to do it.

This family-run farm has been making award-winning cheeses and pure maple syrup for generations, and a visit here gives you a real taste of Vermont’s agricultural roots.

Inside the farm shop, you can sample a variety of cheeses, from sharp cheddars aged up to six years to unique flavors like smoked and maple-infused.

The tasting is free, and the staff are always happy to share tips on pairing and their favorite ways to enjoy each one.

Don’t skip the maple syrup tasting either – they offer four grades of syrup so you can see how the color and flavor deepen as the season progresses.

After your tasting, take a short walk around the property. There’s a maple sugaring house where you can learn about how sap is turned into syrup, and the views of the surrounding countryside are especially beautiful in the fall.

10. Browse the Woodstock Farmers Market

The Woodstock Farmers Market isn’t your typical roadside stand, rather it’s a vibrant gourmet market that’s impossible to get enough of!

Packed with fresh produce, local cheeses, baked goods, and ready-to-eat meals, it’s the perfect spot to stock up for a picnic or grab a quick bite before hitting the road.

In the fall, the market is overflowing with seasonal favorites like crisp Vermont apples, fresh apple cider donuts, and colorful pumpkins and gourds.

The prepared foods section is also worth exploring! Think hearty soups, sandwiches, and salads made with local ingredients. It’s an easy place to pick up snacks or a light lunch if you’re out exploring all day.

If you’re spending a fall weekend in Woodstock, expect it to be busy, especially during peak foliage season. But don’t let the crowds deter you – it’s worth a stop to experience a slice of local life and take home a few Vermont-made goodies.

Where to Stay in Woodstock, Vermont

Woodstock is full of charming places to stay that are perfect for a fall weekend getaway. Whether you’re after a luxury resort, a cozy B&B, or a budget-friendly inn, there’s something for every style and budget.

Staying in or near the village makes it easy to explore all the best things to do in Woodstock without spending too much time in the car.

Just make sure to book your accommodation in advance, as Woodstock is one of the most popular places to stay in Vermont in the fall!

Here are a few great options to consider:

• Woodstock Inn & Resort – The most iconic place to stay in town, with beautiful rooms, a spa, and stunning grounds that look especially magical in the fall
• 506 On the River Inn – A boutique inn just outside the village with river views, cozy common spaces, and a great breakfast
• The Shire Woodstock – A budget-friendly option with comfortable rooms and a convenient location within walking distance of the village
• Sleep Woodstock Motel – A simple, clean, and affordable choice just a short drive from downtown
• The Jackson – A luxurious B&B known for its elegant rooms, gourmet breakfasts, and peaceful setting away from the crowds

Where to Eat in Woodstock, Vermont

Woodstock has plenty of great spots to eat, from cozy cafés perfect for a fall morning to farm-to-table restaurants serving hearty Vermont fare. Whether you’re grabbing a quick lunch between exploring or settling in for a special dinner, there’s no shortage of delicious options.

Here are some top picks:

• Mon Vert Café – A popular breakfast and lunch spot with great coffee, fresh pastries, and hearty sandwiches
• The Prince & The Pauper – A long-standing favorite for fine dining, offering a seasonal menu in a warm, intimate setting
• Worthy Kitchen – A casual eatery with craft beers, burgers, and plenty of vegetarian options
• Abracadabra Coffee Co. – Perfect for a quick morning stop, with excellent coffee and freshly baked goods
• Dreamscape Coffee – A cozy spot for breakfast or brunch with homemade quiches, baked goods, and sandwiches