There’s a reason Woodstock is known as one of Vermont’s best towns, and once you get there, it’s really hard to disagree. Between the charming covered bridges, picturesque town center, and mountain scenery, it’s one of those places that’ll have you looking up houses for sale on Zillow to see if you can move there 😉
I’ve been to Woodstock so many times over the last 20+ years, and I’ve visited in every season. I’ve done day trips and longer getaways, and have pretty much explored everything there is to do in town. This post is my ultimate guide on the best things to do in Woodstock, VT to help you plan the perfect itinerary. I’ll share all my must-see spots, and then go into some more worthwhile attractions that are perfect if you’re planning to stay more than a day.
And with that, let’s get started.
New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our Privacy Policy.
Top Things To Do In Woodstock, VT
1. The Village Center & Town Green
Woodstock’s main area is centered around the town green, and from there, you can walk to most of the shops, restaurants, and a covered bridge (but I’ll share more about the covered bridge in the next section 😉).
This is likely where you’ll spend most of your time, especially if you’re just here for the day. It’s not a large area, but it’s got enough shops and such that you can easily spend a couple hours just wandering around at a leisurely pace. This is also where you’ll find the Woodstock Inn & Resort, the town’s most luxurious hotel with beautiful grounds.
My favorite shops to visit while here are:
→ Clover
→ Woody’s
→ F.H. Gillingham’s
→ Vermont Flannel Company
→ Yankee Bookshop
→ 121 Home
While in this area, you’ll want some time to just meander the side streets. If you cross Middle Covered Bridge in town, heading up Mountain Road, and also along Pleasant Street – plus so many more – you’ll find charming streets and beautiful houses. It’s nice just walking around and taking it all in.
2. The Covered Bridges
Woodstock is home to three covered bridges:
→ Middle Covered Bridge, which is located right in the village center
→ Taftsville Covered Bridge, which is best to drive to
→ Lincoln Covered Bridge, which is definitely a drive, but a short one from town
Middle Covered bridge, I think, is the prettiest in town, and is easily found right by the Town Green. It’s just so perfectly situated, and creates such a pretty postcard-worthy moment that makes the town so special and beautiful. It’s also a very popular photo spots, so during peak times, you’ll want to get there early in the morning if you want to snap any pictures without any people. Be sure to also walk across the pedestrian side of the bridge and enjoy the views from the other side – it looks a little different on the back side.
Taftsville Covered Bridge is a pretty red bridge, and you’ll likely cross it on your way to Sugarbush Farms, which I’ll talk about later in the post. This one is harder to see, but there’s a small pull-off on the road around these GPS coordinates: 43.631451872681986, -72.46929442044394. You can park there for a few minutes, and take in the views of the bridge sitting over the river for the best photos.
Once you cross Taftsville Covered Bridge, there’s some “unofficial” parking spots near the river, and this is a spot that some folks will use as a walking path starting point. It offers nice river views along the way, if you’re looking to stretch your legs for a bit.
Lincoln Covered Bridge is heading out of town on the opposite side from Taftsville, and is located right by the Lincoln Inn. This one is the hardest to stop and visit, as there aren’t a lot of safe places to pull over and walk around, but you can easily drive by it.
3. Sugarbush Farms
No trip to Woodstock is complete until you’ve visited Sugarbush Farms to sample some of their own cheeses and maple syrups, all of which are made right on the farm.
Located only a short 15 minute drive from the main village, not only is the surrounding farmland beautiful, but you’ll get to nibble on samples of their 15 different cheeses, taste their maple syrups, and take a self-guided tour through their woods to see where the maple syrup trees are tapped.
Their grounds are also beautiful, and they have some easy trails through the woods that they allow visitors to explore. You can head out and look for the hidden chapel, too, which is such a cool spot.
From their main tasting building, you’ll enjoy stunning views of the surrounding mountains, which is especially beautiful during fall foliage season.
The drive to Sugarbush Farms ends with a trip down a long, bumpy dirt road. You’ll want to drive slowly, but it’s worth it! The drive is so pretty through the countryside and back roads – you’ll see some really nice scenery along the way that makes this spot extra worthwhile.
4. Marsh-Billings-Rockefeller National Historical Park
Most people skip the Marsh-Billings-Rockefeller Historical Site in town, and I think that’s a mistake. This spot is completely free to visit and park at, and it offers some lovely trails through the woods, a historic estate with gardens, and some cool hiking opportunities.
Home to over 20 miles of trails to explore, it’s a pretty large park with options for all skill levels. For a short and easy visit, I recommend checking out the historic George Perkins Marsh estate, which does tours inside for history buffs (additional admission fee applies), but you can also walk around the grounds and gardens for free. This is a short walk from the entrance, which is a bit uphill, but doable for most people since it’s very short. When you arrive, veer left, and you’ll run right into it.
For easy walks through the woods, the carriage trails can be found by veering right from the entrance, and there are several to choose from. You’ll want to take a look at the trail maps here. For a longer hike, heading out to The Pogue is a great idea. Full disclosure, I haven’t been able to do it because each time I’m visiting and have the time, the trail has been closed for maintenance, or the weather didn’t work in my favor. However, I’ve spoken with some locals who say the hike out to this hidden pond in the woods, surrounded by mountains, is honestly stunning.
Parking: The entrance sits across from the Billings Farm Museum, so you’ll want to park in the Billings Farm lot, walk toward the entrance, and then you’ll see a path on your right that leads back to the main road. There’s a pedestrian crosswalk that leads you to the park entrance.
5. South Peak Overlook
This trail can be accessed through the Marsh-Billings-Rockefeller park, or can be done as a separate excursion, so I wanted to give it its own section. Either way, it’s one of my favorite spots in town that’s worth doing when you visit.
The South Peak Overlook sits on Mount Tom, which is the highest peak in town. However, this particular overlook doesn’t reach the actual summit – making it a more accessible option for many skill levels. The overlook, however, offers panoramic views of the town and mountain vistas, making you feel like you’re at the summit.
Most people get up to the overlook by taking the Faulkner Trail, which starts at Faulkner Park in town. 85% of the trail is very, very easy due to strategic switchbacks carved along the mountain – you hardly notice the incline at all. Toward the top of the trail, the switchbacks get shorter, and more noticeable, and then the last 5-10% is a rock scramble, which does make it more difficult.
Once you get to the top, you’ll see the giant Woodstock Star, which is lit in the window, and can be seen from town. There’s a great view from there, but you’ll want to walk past the star, and veer left a bit, and walk down that path to get to the viewpoint in the photo above.
You can also access this overlook from the trails in the Marsh-Billings-Rockefeller park to make it a longer hike.
6. Billings Farm & Museum
Part of the Marsh-Billings-Rockefeller park, the Billings Farm & Museum is considered one of the best rural farming museums in the entire country. There’s an additional fee to enter the museum, and is considered one of the top attractions in town.
Here’s my honest take on the museum: It’s very pretty, but unless you’re with children, or have a specific interest in history and farming, you can probably skip this one. I really do recommend it if it sounds up your alley, as the museum is interactive, and very well done. It’s also a working dairy farm, and for that reason, is really interesting to explore and learn about.
But, it can also feel a bit boring for those who really have no interest in these topics. So that’s what I usually tell people when planning their visit.
It’s especially great if you have children with you because they have a lot of exhibits and events at the farm that are especially perfect for little ones.
7. Hike Part Of The Appalachian Trail
In keeping with the theme of hiking, you can hop on part of the Appalacian Trail in Woodstock, which is really cool. Most folks will use the AT Trailhead located along Route 12, located around: 43.655235579894835, -72.56612727352544.
From here, it’s a short hike option along the AT, which brings you to some rural clearings with beautiful countryside views. There are a few options to explore here, and a great one to pick is Luce’s Lookout, which is a moderately challenging trail that leads to a wooden fire tower with beautiful mountain views. This one is especially pretty in the fall.
8. Abracadabra Coffee
Located close to the Route 12 AT trailhead is Abracadabra Coffee, and it’s my favorite spots for coffee in Woodstock. I think it’s absolutely worth the drive from town to get here.
Located in a rustic barn-like building, it’s out in the country surrounded by mountain and rural scenery, and they also have outdoor seating along the little brook that runs through their property for the perfect vibes.
They roast their beans in-house, and their drinks are so well balanced and amazing. They also sell their beans, and I highly recommend their Dark Times roast, which is what they usually use to prepare drinks at the café. It’s got a nice, coffee flavor without being bitter at all – it’s really great, and I love recommending this spot for coffee when visiting.
Pro Tip: It’s also not far from On The Edge Farmstand, which is most often open on weekends, and a great little farm stand to visit.
9. East End Park
A lot of people drive past this cute little park, and completely miss the lovely scenery back here! In fact, I didn’t even discover it until a few visits ago, and it’s now one of my favorite places to stop at in town.
This park sits along the Ottauquechee River, and this is also where you can start the Ottauquechee River Trail for an easy walk in town. You’ll also find picnic tables, and benches here, plus the Char Woodfired Pizza Truck is also parked here, and usually open most days (except Tuesdays) in-season. But hours of the truck can change, so be sure to check before making plans to eat here.
10. Woodstock Farmers Market Store
Just outside of the main village area, you’ll find the Woodstock Farmers Market store, which isn’t a traditional farmers market with tables and tents – it’s an actual store that’s open year-round with all kinds of wonderful things.
You’ll find everything here from farm fresh flower bouquets (in season) to prepared foods, coffee, breakfast sandwiches, a small grocery section, local produce, and more. It’s a small store, but they carry a wide variety of things, and it’s one of those spots where I always walk out with something.
It’s worth the short drive from town, for sure!
11. Craft Cocktails At Au Comptoir
Located right in the main village area on a side street, you’ll find the lovely Au Comptoir, which is a craft cocktail bar that also serves small plates that you can easily make a meal out of. But, of course, their focus is their seasonal cocktails, which are expertly crafted by a mixologist.
The interior is also impeccably designed, and they have a small outdoor seating area that’s also open in the winter, and warmed with fire pits.
In addition to visiting as a customer, you can also book private mixology classes, which includes a welcome glass of bubbly, a cheese board to munch on, and you’ll learn how to become an expert at mixing two cocktails of your choice.
12. Visit A Charming Flower Stand In Pomfret
Just outside of Woodstock in the neighboring town of Pomfret, you’ll take a scenic drive through the countryside to Brook & Blossom flower stand, which is opening seasonally and offers beautiful, farm-fresh flower bouquets that go beyond the standard flowers you’ll find at supermarkets.
I love to stop here on my way home to get fresh flowers for my house. They accept Venmo, too, which makes it very easy if you don’t have cash on you.
13. Farmhouse Pottery
This pottery shop is now sold in stores nationwide, but it began as a small business right in Woodstock. Their flagship store and pottery studio is open to the public, and located just a short drive from town center.
In addition to their shop and pottery studio, you can also book a private wheel workshop. Led by one of their artisans, you’ll learn how to work with clay on the wheel, and make your own creation to take home. I did this once with my husband, and we still talk about how much fun it was. They provide either mimosas or light bites, and they fire your piece, and ship it to your house, all included with your workshop session.
14. Admire Fall Foliage
It’s no secret that Woodstock is one of the top fall foliage destinations in Vermont, and it’s one that I also recommend on my fall road trip itineraries. It’s one of the foliage spots in New England that is worthy of the hype it receives.
The most important things to know about foliage in Woodstock:
→ It’s very crowded during peak times, especially Indigenous People’s Weekend. Foliage in Woodstock peaks around mid-October, just after Stowe, so the first half of October is always very busy. Especially on weekends.
→ Most of the best foliage spots are outside of the main village. The sidewalks in town are lines with some pretty fall trees, and the fall atmosphere is very on point. But the biggest displays of fall color can be found out in the countryside along the back roads. The best places are Sugarbush Farms, including the drive out there, and Old River Road near Billings Farm.
→ The famous Sleepy Hollow farm landscape and the surrounding access roads (including Cloudland Road) are closed in the fall season due to over-tourism. I purposefully no longer recommend driving by Sleepy Hollow Farm, for this reason.
→ It’s good to remember to be respectful of private property during your visit for this reason. Sleepy Hollow Farm is actually a private farm, and not open to the public. It got so overrun with tourists trying to get the perfect photo by trespassing onto their property, and traffic was getting very backed up that it completely disrupted the everyday lives of the locals in the area. To keep other places in New England open and accessible for all to enjoy, it’s imperative that we all respect private property during our visits 😊
15. Celebrate Christmas With Wassail Weekend
Known as one of the best Christmas festivals in New England, Wassail Weekend in Woodstock is the perfect holiday getaway to plan in December. The town is beautifully decorated for the holidays, and offers fun things like carriage rides through town, special holiday markets, and fun holiday events at Billings Farm.
16. Go Skiing & Snowboarding In The Winter
Woodstock is home to Saskadena Six, which is one of the oldest ski destinations in the U.S. It’s on the smaller side, but a wonderful place to visit for fewer crowds. It’s got a lot of options for intermediate trails, plus great options for both beginners and more advanced skiers, too.
If it’s cross-country skiing you’re after, Woodstock has that, too! The Woodstock Nordic Center (run by the Woodstock Inn & Resort) is home to over 25 miles of groomed trails for cross-country skiing and snowshoeing. They also have options for fat biking.
17. Winter Sleigh Rides
There are a couple places in and around Woodstock that offer winter sleigh rides – Billings Farms & Museum, and Kedron Stables (which is just a short drive outside of Woodstock). Both are great options if you’re looking for something fun to do during a winter getaway, but aren’t into skiing or snowshoeing.
Things To Do Near Woodstock, VT: Easy Day Trips & Excursions
While there are so many great things to do right in Woodstock, VT, there are also lots of opportunities to explore the nearby areas to see even more of Vermont and New England. If you’re planning a trip to Woodstock and have some extra time, I highly suggest you look into some of these options.
18. Quechee
Located only about 14 minutes from Woodstock, Quechee is such an easy and worthwhile excursion to make when in the area. While it doesn’t have a super walkable town center since it’s more spread out, there are enough things to do to fill up an entire afternoon – or even day!
These are my favorite things to check out in Quechee:
→ Simon Pearce Flagship Store & Restaurant. You can enjoy free glass-blowing demonstrations, shops pretty much everything they make, and also have lunch or dinner overlooking the river in what has been called the most romantic restaurant in the U.S.
→ Visit the Quechee Covered Bridge, which is within walking distance from the Simon Pearce store.
→ Quechee Village Shops, which is a cute little outdoor shopping plaza with character, and home to a large antiques store, country store, and much more.
→ Quechee Gorge, which you can just take a quick look at from the bridge, or walk. the trail around it if you have time.
→ VINS nature Center, which is a wonderful attraction with a fully-accessible canopy forest walk, plus wild bird rehabilitation exhibits.
→ Whiskey tasting at WhistlePig, which is close to Simon Pearce and the covered bridge, and has a very cool speak easy vibe to it. Intended for readers 21+, and please drink responsibly.
19. Killington
Located just 30 minutes from Woodstock, Killington makes for a very cool day trip for those who are looking for more adventure. It’s truly a playground in terms of outdoors activities. Ranging from scenic gondola rides to Killington Peak, hiking, and finally, to a full-on Adventure Center with ziplines and a mountain coaster, it’s packed with options to fill up an entire day.
Psst! I have a full guide on the best things to do in Killington, VT, if you need more ideas 😉
20. Plymouth
Plymouth is also a short drive from Woodstock, usually taking just 20-25 minutes, and it’s got some really cool places to check out.
The Calvin Coolidge State Historic Site is a preserved village and birthplace/childhood home of the 30th U.S. president, Calvin Coolidge. Perfect for history buffs, you can actually step inside the family parlor where he was sworn into office by his father in 1923.
The grounds are free to walk around, but it’s got multiple buildings that serve as a museum, which does require a paid admission to experience. Nestled among the mountains of Plymouth Notch, including Coolidge Homestead, birthplace, church, one-room schoolhouse, historic barns, general store, working cheese factory, and museum
Plymouth Cheese Co. is just down the street from the Historic Site, and you can easily walk between the two. This cheese shop has been using the same cheddar recipe since the 1890s, and was founded by President Calvin Coolidge’s father. Inside, you can sample their cheeses, and of course, purchase some to bring home.
Camp Plymouth State Park is also a wonderful stop to make in town, which is home to a small sandy beach on a lake, and they also rent out boats to explore the water on.
21. Stowe
Best as a day trip since it’s about an hour and 20 minutes from Woodstock, Stowe is another wonderful town to explore in Vermont. It’s equally as charming, and just has more of a mountain town vibe, but is home to Vermont’s highest peak, scenic gondola rides, great hiking spots, a cute little Main Street, and gorgeous scenery.
Psst! I have some guides all about Stowe, including the Best Things To Do In Stowe, VT, and Fun Things To Do In Stowe, VT In The Winter, if you need more ideas 😉
Woodstock does such a great job celebrating holidays and bringing the community together. One of the best things to do in Woodstock, VT in the fall is to admire all the fall decorations around town. Storefronts and houses alike will be adorned with fall wreaths, pumpkins and all kinds of harvest decor to get you in the fall spirit.
While Vermont is known for its maple syrup, cheese and Ben & Jerry’s ice cream, it’s also known for its maple creemees, and getting one of these should definitely be on your list. A maple creemee is basically maple-infused soft serve ice cream, and it’s awfully delicious, especially during this time of the year. The best place to get a maple creemee in Woodstock is at Woodstock Scoops, which can be found right in the town center.
Psst! I have an entire post on the best times and places to see fall foliage in Vermont, if you need more information to time your visit just right 😉
Where To Stay In Woodstock
Most of the time, I highly recommend staying in a hotel that’s walkable to the town green, and the shops/restaurants. This is largely because most people tend to visit during peak foliage season, and parking around town can be difficult if you have to drive in each time because of the crowds. That said, there are some really great places to stay that are just a short drive from the town center that are also worth it if you happen to be visiting on a weekday, or outside of peak times.
Top Luxury Pick: Woodstock Inn & Resort
Honestly, this is one of those hotels that’s worth the cost. The location itself is fantastic, and located right in the heart of the village, so you can walk to all the shops and restaurants in that area, and you’re petty much across the street from Middle Covered Bridge. The rooms are beautiful, and they also have a great spa and on-site dining.
→ Click here to check rates & availability at the Woodstock Inn & Resort
The Vesper: Great Mid-Range Option (Walkable To Town)
This is a great option if the Woodstock Inn & Resort isn’t in your budget. It’s a modern, mid-century boutique hotel that’s walkable to town (not quite as easy as the Woodstock Inn, but still very easy).
→ Click here to check rates & availability at The Vesper
Inn On The River: Great Mid-Range Option (NOT Walkable To Town)
For a nice mid-range option that’s just a short drive into town, the Inn on the River is one I’d recommend. This is usually where I’ll stay when visiting in the off-season, or on weekdays, when I don’t need to worry as much about parking right in town. It’s a cozy inn with spacious rooms, and sits right on the river. They also have a nice bistro in-site.
→ Click here to check rates & availability at the Inn On The River
Visiting Woodstock, VT: Answering Your Questions
Best Time Of Year To Visit
Woodstock is really a great town to visit year-round because it’s so charming, but fall and winter get my vote for best seasons to visit. The fall foliage in Woodstock is truly stunning, and the winter season makes for such a cozy getaway (even if you don’t ski or enjoy snow activities).
If you plan to explore more of the state during your visit, the best time to visit Vermont in general, I think, is the fall season to admire the foliage.
How To Spend A Day In Woodstock, VT
If you’ve got more limited time in Woodstock, I would prioritize the town center and shops, Sugarbush Farms, and having lunch somewhere. Mon Vert Café right in town is a great lunch spot, but it gets very busy, so you’ll want to plan accordingly. If you have extra time for a full day, I would add trails at the Marsh-Billings-Rockefeller park.
Is Woodstock Walkable?
Yes and no. The main village/town center is very walkable, and from here, you can visit most of the shops in town, quite a few places to eat, Middle Covered Bridge, and picturesque side streets. However, to get to places like Billings Farm and Sugarbush Farms, you’ll need to drive.
Is Woodstock Always Crowded?
It really depends on the time of year, but generally, it’s one of the busier towns in Vermont because it’s such a beautiful destination. It pretty much sees tourism year-round, but the fall season brings the most crowds. The first two weeks or so on October is when Woodstock is the busiest and most expensive to stay in.
I’ve been in all seasons, including mid-spring (April), and my general experience is that outside of the fall season, the crowds are manageable, and don’t really impact your visit much.
More Of My Vermont Travel Guides:
- Vermont In The Fall
- Vermont In The Winter
- Vermont In The Spring
- All The Best Things To Do In Vermont
- Best Places To Stay In Vermont In The Fall
- What Is Vermont Known For? I’ll Tell You!
- Vermont Covered Bridge Road Trip Itinerary
- Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
- Christmas In Vermont: All The Most Festive Things To Do
- Best Things To Do In Waterbury, VT
- Awesome Corn Mazes In Vermont
- Must-See Places On A Vermont Route 100 Road Trip
You may also enjoy:
- Best New England Winter Getaways
- Best New England Christmas Towns
- Best Day Trips In New England
- The Perfect New England Fall Road Trip
- Vermont vs. New Hampshire In The Fall
That’s A Wrap On The Best Things To Do In Woodstock, VT
Now that you know all the best things to do in Woodstock, VT, you’re ready to plan your perfect New England vacation in Vermont! Whether you’re looking for a little R&R at the Woodstock Inn’s spa, or are excited about the outdoor activities like hiking and tree canopy tours, there’s a little something for everyone that makes this one of the best towns in Vermont to visit.
