Fall is the best time to visit Woodstock, Vermont! The leaves are changing colors, festivities are in full swing, the air is crisp, and the town looks like something out of a movie! Throw in a classic New England bed and breakfast, and you’re all set. Here’s my list of things to do in Woodstock Vermont!

outside sleepy hollow farms in Vermont

It’s my favorite time of the year again – fall!

And there’s nothing like leaf-peeping in New England. The fall foliage in Stowe and Woodstock is unreal. It’s something out of a magazine. It’s something that I highly recommend for anyone who loves autumn as much as I do. Crisp yellows, burnt oranges, and if you’re lucky, a full-on fire engine red. 

Being from Texas means that we don’t get to experience a real autumn here. The leaves don’t really change colors. They’re usually bright green one day and brown the next. Pumpkins don’t show up on front porches until a week before Halloween because it’s honestly too hot and they would melt.

That’s not the only reason I love Vermont though! They have some of the highest quality fresh produce, maple syrup, and dairy, so you know everything you’re going to eat is going to be farm fresh and delicious. And all I’m really trying to say is that Woodstock is the perfect fall weekend trip to make with your beau. It’s laid back and oh, so perfect for the season. 

Here’s everything you need to do, when to go, and what to know for your fall Vermont trip!

yellow leaf outside FH Gillingham & Sons
random red barn
Vermont maple syrup bottle
hydrangeas on white picket fence
house on a hill

Things to know:

When is it peak fall foliage in Woodstock, Vermont?

It can vary quite a bit! There are plenty of websites that have predictors if you’re planning a trip. It’s most helpful to look at last year’s peak foliage dates when booking a fall foliage trip to Stowe or Woodstock, VT, and use that to plan your trip. Here is a website that will give you an idea of what dates were best for leaf-peeping last year. I find that anywhere between October 5th-20th tends to get you decent colors!

How far in advance do you recommend booking a fall foliage trip?

Seeing fall foliage is one of the best things to do in Woodstock. So naturally, everyone flocks to Vermont during this time. We booked our trip 4 months in advance, and it proved to be late. A lot of the inns and bread and breakfasts we wanted to consider were already fully booked out for our dates. So if you’re serious, I would have your trip booked 6 months in advance. This will guarantee you have a chance to snag affordable accommodations. Keep in mind that Woodstock is really small, and there aren’t too many inns around. Airbnb or VRBO might be something to consider too. You may also want to consider staying in Lebanon, NH and driving into Woodstock for the day.

How many days do you recommend for Woodstock? 

Woodstock is tiny. Tiny enough to bike and see the whole place! But there are activities to do here in Woodstock and in neighboring towns. I would say you don’t need more than a 48-hour weekend to see and do everything!

The airport at Burlington is SMALL, and the car rental agencies don’t always have their act together. 

Since we were flying in from Houston, Burlington was the nearest airport to Woodstock. Keep in mind – Burlington Airport is SMALL. And I mean really small. The car rental agency we used made us wait close to 2 hours even though we had a car reserved for pick up. I don’t know if it’s the labor shortage or if it’s something that’s normal because of the time of year. But this is something to keep in mind. Plan on waiting. This obviously wouldn’t be an issue if you live close and make a road trip from Boston, Albany, New York City, or somewhere else close by!

fall at the Laundry room in Woodstock,VT
Outside Farmhouse Pottery in Woodstock, VT
cow on green grass
manor lined with pumpkins

What to do during Fall in Woodstock, VT.

  • Ride the Green Mountain Railroad: located ~45 minutes outside of Woodstock, this is a great way to see all the fall foliage! Guests of the Green Mountain Railroad enjoy a 2-hour trip through Vermont’s scenic countryside during September and October. Overlook mountain, rivers, and wildlife from the windows of the rail cars. They also offer a 4-course dinner train.
  • Middle Covered Bridge: When I think of Woodstock, this is the first image that comes to mind. The quintessential perfect covered bridge. Be prepared though, there’s almost always a crowd here.
  • Visit Farmhouse Pottery: A lot of the props I purchase for the blog are from here, so I spent the better part of the afternoon in this store and couldn’t pass up the chance to add this to my list of things to do in Woodstock. I walked away with a few things, but the best part is that they offer to ship the items to your door – perfect if you’ve only brought a carry-on!
  • Wander Around Pleasant Street: Lots of colorful attractions are located here. Take a peak inside a few shops. Grab a bite to eat; it’s the perfect way to spend a lazy Saturday morning. There’s a little park towards the end where the Woodstock Inn is located and there are often vendors set up in the park setting knick knacks and such.
    • TIP: come early and be prepared to walk around! If you get here early, you’re more likely to get a good parking spot – without having to drive around for a while. Plan to be on foot for the rest of your stay in downtown because the spots are almost always full.
  • Check out the Woodstock Inn & Resort: During the holidays, this place is fully decked out with festive flowers and lots of pumpkins. Unfortunately, we made it the week before all the flowers were replaced with yellows and oranges. But nonetheless, this is a sight to see on your stroll.
  • Sleepy Hollow Farm: The most beautiful farm! Keep in mind that the farm is private property, and though they don’t mind visitors stopping by, you don’t want to go past the barriers they have set up. They have cameras everywhere, and I would encourage everyone to respect the private property signs! 
    • TIP: A lot of the images you see online are a bit misleading as they’re taken much further down the driveway of the farm. I don’t recommend doing this unless you’ve obtained special permission to do so!
    • 3429 Cloudland Rd South, Woodstock, VT 05091
  • Billings Farm & Museum: This place is on the way to the Sleepy Hollow Farm. It’s a classic creamery with tons of animals. It’s a great place to take the kids if you’ve got the little ones with you! They also have an ice cream shop on the premises.
  • FH Gillingham & Sons: Located near the main street. This is a classic Vermont General Store in Woodstock’s downtown that sells a little bit of everything! From pottery to kitchen utensils, cider, pumpkin butter, and so much more.
  • Jenne Road Farm: This farm is located a little outside of Woodstock, located in Reading. It’s a bit more difficult to find, but here you’ll see cows roaming the land and an iconic red barn with mills!
    • TIP: This farm is located at a higher elevation. Meaning that if it’s a particularly cloudy or foggy morning, you may want to get here later in the day. That way your pictures aren’t just a bunch of fog!
    • 1279-1163, Jenne Rd, Reading, VT 05062
  • Taftsville Covered Bridge: just a place to stop for a quick picture; it’s a red covered bridge. Keep in mind there isn’t much parking here, so you’ll want to steer off the road or maybe opt to just drive under the bridge instead.
  • Woodstock Farmers Market: Don’t be fooled by the name – this is not your typical farmers market lined with vendors! This is more of a grocery store. But it’s a lot of goods from local farmers in the area and locally sourced ingredients. This place is close by to Farmhouse Pottery and has prepared snacks, hot cider, and everything else. Visitors often make a pit stop in here to grab a warm drink, a sandwich, or souvenirs!
  • Sugarbush Farm: A cute little family-owned farm with acres and acres of land. Taste Vermont cheddar, maple syrup, and so much more. The employees are all so nice here, and they even have a maple syrup museum. It gave me Stars Hollow museum vibes (if you know, you know) but it was still cute! Make sure you stop by the gift shop to pick up maple syrup. We loved the flavor of their dark amber maple syrup.
  • Quechee Gorge Trail: a 2.7-mile (that’s roundtrip) hike with beautiful views. This is located inside Quechee Start Park and is a great way to see the fall foliage in the early morning hours! Stop by the Skinny Pancake afterward for a nice, hearty breakfast!
    • TIP: Even if you decide not to hike the trail, I do suggest stopping at the viewing point at the top to take a picture. The gorge looks stunning with all the fall foliage and definitely a must-do on my list of things to do in Woodstock.
  • Take the scenic route to Stowe: Depending on how much the leaves have changed color, you might want to consider taking the scenic route to Stowe (if you’re headed there.) This does add ~40 minutes to the drive time than if you were to take the highway, but depending on the time of year, it might be worth it! Otherwise, hop on the I-89N and make your way into Stowe.
Jenne Road Farm
Woodstock Middle Bridge
Quechee Gorge overlook from the street
quechee gorge bridge in the distance
taftsville red covered bridge

Where to eat in Woodstock, VT

  • Mon Vert Cafe: We loved this place; there was just so much on the menu to enjoy! They offer bakery items, breakfast, lunch, and a wide assortment of hot and cold drinks. Try the fall foliage latte – it’s sweetened with real maple syrup, and it’s so warm and cozy!
    • 28 Central St, Woodstock, VT 05091
  • Worthy Kitchen: Make sure to make reservations; this place is always packed. They’ve got burgers, mac and cheese, and farm-fresh eats on the menu.
    • 442 Woodstock Rd, Woodstock, VT 05091
  • The Skinny Pancake: Located not far from the Quechee Start Park, this is a great place to stop by and grab breakfast on your way into Woodstock.
    • 7161 Woodstock Rd, Quechee, VT 05001
coffee outside mon vert cafe
lunch at Worthy Kitchen
husband at worthy kitchen
sautéed mushroom and spinach sandwich with Vermont cheddar from Mon Vert Cafe

I hope this gets you in the mood for fall.

I’m ready for pumpkin spice lattes, cozy sweaters, and spooky season!

yellow leaves in front of a traditional house in Woodstock

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