20 Fantastic Things to Do in Woodstock, Vermont (2023)

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Anytime is a great time to travel to Vermont, especially when visiting one of its best small towns: Woodstock.

All four seasons provide endless possibilities for amazing things to do in Woodstock, Vermont.

Whether you’re envisioning a horse-drawn sleigh through a picturesque village on a snowy winter evening or a cozy breakfast steeped in fresh maple syrup on an autumn morning, Woodstock, Vermont does not disappoint.

Woodstock has consistently been named one of the best places to visit at Christmas and one of the most beautiful towns in America.

It offers a plentitude of outdoor activities, culinary delights, historic and cultural offerings, and so much more.

No matter what season you visit, here are the absolute best things to do in Woodstock, Vermont throughout the year!

An empty road winds towards a bright red farm in fall.

Travel Essentials for Woodstock, Vermont

 Of course, there are few travel basics and FAQ that should be considered when planning a Woodstock VT trip, like transportation and timing. Below are some important things to think about while planning your trip.

When is the Best Time of Year to Visit Woodstock VT? 

Flowers blooming in front of a view of fields and mountains in Woodstock Vermont
Walking through Vermont farmland 

Woodstock is one of those places that is lovely to visit year-round and has so many things to do no matter what the season. However, I think autumn is a wonderful time to go to Woodstock Vermont because of the bright, colorful leaves.

There are many online foliage maps that you can reference to align your travel with the autumn colors, but fall in Woodstock generally is at its best in mid to late September and early October.

Where is Woodstock, VT?

If you’re wondering where Woodstock Vermont is located, it’s in the east-central area of Vermont, roughly 15 miles from the border of New Hampshire. Woodstock is considered one of the best towns to visit in Vermont, too!

It’s an essential stop on a Vermont road trip, and an easy day trip from other Vermont destinations, such as Burlington, Stowe, and Manchester.

How To Get to Woodstock

This area is most accessible by car. The cities of Boston, MA, Albany, NY and Portland, ME are all within a drive of two to three hours. The cities of Burlington, VT and Manchester, NH are about 90 minutes away by car. All of these cities have major airports, with Boston, Albany and Portland having the most flight options.

With these travel basics, you can start planning the perfect Woodstock getaway.

The Woodstock, Vermont covered bridge is seen with fall foliage behind and flowers in front
This is one of the most popular Woodstock, Vermont covered bridges!

The Best Things to Do in Woodstock VT

From sampling Vermont’s famous cheeses to hiking to strolling the historic Woodstock downtown, you’ll find a plethora of activities to keep you and your loved one busy on your Vermont vacation. It’s just a matter of choosing from the menu of fun and deliciousness!

Sample Cheese, Cheese, and More Cheese

No Vermont vacation is complete without cheese.

In the past, it was said that Vermont had a larger population of cows than people! Not hard to imagine, with farmland stretching for miles across the state. Either way, those cows are producing some great dairy, and Vermont’s cheesemakers are turning it into the finest cheese.

Cabot is the state’s most famous cheese purveyor, available in stores throughout the US. You can’t go wrong with a nice block of Cabot sharp cheddar. But when in Vermont, you want to try ALL THE CHEESES.

You can have a wonderful cheese feast at Quechee Gorge Village. As you walk through the village’s cute shops, you’ll find a huge spread of cheese samples, along with crackers and jams.

Give all the varieties a taste and buy a block to take home. With the abundance of cheese to sample, you may find it hard not to get greedy!

Cabot is not the only cheese in Vermont, not by a mile. A visit to Woodstock, VT demands a visit to a local farm.

A brown horse standing next to a red fence in Woodstock Vermont
One of the top Woodstock VT things to do: meet the locals!

Head up to Sugarbush Farm, a Vermont sugar house and 3 generation family farm tucked away in the hills, for more cheese sampling as well as maple syrup tasting.

While you’re there getting your fill of farm-made cheese, you can also walk around the 500 acre property, visit with the goats and horses, and learn about how maple syrup is made. 

Small cabin seen between trees in the forest in Woodstock Vermont

If you venture into the woods bordering the farm, you’ll find an interesting treasure: a small chapel tucked between the trees. This sweet spot is even available to be booked for intimate country weddings. 

Stroll America’s Sweetest Downtown

Woodstock Vermont town square with brick shops in the distance, a man pushing a stroller looks at the camera

Downtown Woodstock, VT is a fabulous place for shopping, dining, and more. This cute area can get crowded on weekends or during busy events, and it’s no wonder–there’s lots to see and do.

There are bookstores, toy shops, clothing stores, and plenty of options for gifts, arts, and crafts.
storefront of an old general store, the sign reads FH Gillingham & Sons.storefront of an old general store, the sign reads FH Gillingham & Sons.

Don’t miss FH Gillingham & Sons, a classic Woodstock VT shopping opportunity in the heart of downtown.

This 1886 general store is a Woodstock staple, and is renowned as one of VT’s oldest family-run general stores. Stop here for all kinds of Vermont-made items, souvenirs, and a nice selection of wine.

Other shops in Woodstock VT to keep an eye out for: 

A row of storefronts next to a sidewalk in Woodstock Vermont
Woodstock VT downtown is one of the cutest downtowns in all of New England

Even if you’re not shopping, downtown Woodstock VT is a lovely place to walk around. You can explore the covered bridge, admire the iconic Woodstock Inn and Resort, or simply sit with coffee and people watch.

You never know who you might meet. On one of our trips to Woodstock, we got to meet this tiny polar bear named Oso.

A white dog on a leash walking down the sidewalk in Woodstock Vermont
Look at this cute pup we met during our Woodstock visit!

Experience a Classic Woodstock Vermont Christmas

Downtown decorated for Christmas in Woodstock VT
Christmas in Woodstock VT

If you’re looking to experience a New England Christmas that goes all in on charm, then you need to plan to visit Woodstock VT for Christmas!

Wassail Weekend in Woodstock is the undisputed star of the Christmas season, and with good reason: carriage rides through downtown Woodstock, historic homes decorated to the nines, and music festivities all around town are just a few of the things that make a plan to visit Woodstock VT for Christmas a must for anyone looking for quaint Woodstock VT activities!

Stroll the Village Green & Woodstock Village

a rocky path runs through a village green in a charming Vermont town. the sky is blue, grass is green, and historic buildings line the roads

Many of the shops downtown and other notable buildings comprise the Woodstock Village Historic District. This was listed on the National Register of Historic Places back in 1973. It includes95 buildings and sites across the village center and along the Ottauquechee. 

The oval-shaped Village Green sits within Woodstock Village. On one side you’ll spot the covered bridge and on the other, the Woodstock Inn andThe Norman Williams Public Library.

North of town are sites such as the Billings Farm and Museum, and parts of the f Marsh-Billings-Rockefeller National Historical Park.

A walk around Woodstock Village will make you feel as if you’ve stepped into a Normal Rockwell painting: a kind of quainter, simpler time that many of us long for.

Visit the Long Trail Brewery

Sampling Vermont beer is a must-do when traveling in Vermont.

When in Woodstock VT, make the quick 15-minute drive west to the Long Trail Brewery to try some of Vermont’s most well-known (and well-loved) beers.

Take a brewery tour, then enjoy beer flights or snacks at their Bavarian-inspired pub. There are nice views and delicious brews–what more do you need?

Visit a Working Dairy Farm – Billings Farm and Museum

a gravel path connects several farm buildings and a historic house on a spring day in vermont. the trees are just starting to bloom

If you’re searching for things to do in Woodstock VT with kids, Billings Farm and Museum should top the list! This is a working farm that is all about demonstrations and education, and is beautiful, to boot!

Billings Farm and Museum is a beautiful property where you can stay busy for hours.

a sheep grazing alone in a green field in vermont

Spending an afternoon here can show you a great deal about the inner workings of a Vermont farm, and you can see the animals up close and personal. 

Sift Through Endless Antiques

a long building with a pink roof, bearing a sign reading Antique Mall

New England is a great place to go antiquing. We’re always surprised at the number of antique shops to be found all over Vermont and New Hampshire.

Well, if you love searching for treasures of the past, we found the trove. In Quechee Gorge Village (the same place where you can sample Cabot cheese) is an enormous antiques mall with several floors filled with antique items of all kinds.

It’s a fascinating place to walk around in. On our recent trip to Woodstock, we ran into some bad weather–exploring this antiques mall was a perfect rainy-day activity!

READ NEXT  12 Amazing Antique Stores in Vermont: Antiquing VT

Sample Local Spirits

After you’ve explored the antiques for a while, head down to the end of the shopping center and visit Vermont Spirits. There you can sample Vermont-made whisky, gin, bourbon, and more.

A free tasting lets you try four different spirits. Get ready to feel the burn a bit, but they are delicious. We liked the 1791 Cocktail, which had a fruity touch.

A glass of beer on a table in Woodstock Vermont
Looking for what to do in Woodstock Vermont? How about sampling some local spirits!

Admire Quechee Gorge

Woodstock and Quechee are neighboring towns in west-central Vermont, and a trip to one can’t really be complete without a trip to the other.

When you’re searching for things to do near Woodstock, VT, also look for things to do in Quechee, VT. There are so many, and Quechee VT to Woodstock VT is a less than 15 minute drive!

a deep gorge with a river flowing through it between two steep tree lined cliffs

One of our very favorite sites in the region is Quechee Gorge. This awe-inspiring natural formation is best seen from the bridge on Route 4. There is a parking area just beyond the Quechee Gorge bridge, and the bridge has a sidewalk with rails, so you can safely walk out and peer into the gorge.

The gorge is especially magical in the autumn, when the trees on either side burst into remarkable hues of orange and red.

If you’re feeling adventurous, you can take a fairly short hike down alongside the gorge. The trail leaves from the parking area and takes you to some short waterfalls.

READ NEXT  10 Breathtaking Waterfalls in Vermont To Visit This Year

Learn About Glassblowing at the Simon Pearce Flagship Store

Glassblowing is a popular art in New England. There are many workshops that offer demonstrations, tours, and even lessons.

A really nice place to see glass blowing in action is the Simon Pearce Flagship Store in Quechee. This place features an elegant glassware shop, a glass-blowing studio, and a bar and restaurant.

Head downstairs first to see the glass blowing in action. Several artisans were at work during our Saturday afternoon visit. Though the room is hot and bright, these blowers seemed perfectly relaxed and happy, creating beautiful glass works with ease.

Watching them is hypnotic, but don’t be afraid to ask questions. The artisans are glad to chat with you and educate you on glass blowing.

Man working in a factory in Woodstock Vermont

You can step through onto the balcony to enjoy the refreshing breeze and a view of the nearby covered bridge and tumbling waterfall.

Head back upstairs and browse the wares of the shop. The shining glassware sparkles as you walk through. You will be hard pressed not to purchase some of their amazing glasses and other amazing creations.

an inviting interior of a restaurant in quechee vermont. wooden tables, a shiny wooden floor, and cozy lights

Finally, stop for a meal, or even just a cocktail, in their on-site restaurant. The food here is divine and the atmosphere the perfect blend of relaxation and luxury. 

Try their Vermont cheese soup if you can and if you are lucky, you might get one of the tables overlooking the tumbling water outside!

a wooden table with several place settings set against a window. outside the window is a man-made waterfall

Explore a Quaint Bookshop

In Woodstock, we saw a sign for used books and had to stop. This eclectic bookstore, Pleasant Street Book Store, had lots of volumes old and new and was a fun place to browse.

They also had a nice view over the river from behind the shop.

When searching for what to do in Woodstock VT, don’t discount those hidden gems that you just might stumble across. However, if you’re keen to visit, try to call ahead as the open hours seem to vary.

A building front with a sign outside saying \

Visit the raptors at VINS

The Vermont Institute of Natural Science (VINS) is a must-do on your Woodstock bucket list, particularly if you’re traveling with kids!

VINS is an organization dedicated to avian rehabilitation and environmental conservation. Every visit there is not only a fun, cool experience seeing birds up close, it’s a lesson in how to better care for our earth and its inhabitants.

a man stands next to a grey stroller looking away from the camera toward a fenced in bird enclosure
My husband and sun checking out one of the birds at VINS

We visited VINS with our one-year-old son recently, and while he threw passing glances at the Snowy Owls and the sharp-eyed hawk varieties, my husband and I were fascinated. 

VINS takes in birds who have been injured and nurses them back to health to be released, if possible. If that is not possible, or they are otherwise unfit for life in the wild, they may stay on at VINS as animal ambassadors. 

a woman with long brown hair wears a leather glove on which is perched a brown hawk, behind them is a green building and trees on a sunny day

When you visit VINS you can see a dozen or more of these amazing raptors in their large enclosures. Throughout the day, staff gives various lectures and programs that allow you to see the raptors in action and learn about them in more detail.

It was pretty exciting when one of their hawks flew right over my head!

After hanging with your new feathered friends, you won’t want to miss the Forest Canopy Walk, which is relatively new to VINS. 

a raised wooden walkway stretches ahead with a towered platform and stairs in the distance. the walkway and platform are among the tree canopy

the entrance to a canopy walkway, a wooden ramp stretches out behind a simple wooden arch

This impressive wooden walkway takes you 100 feet or more over the forest floor, near the bank of the Ottauquechee River.

While there are some parts of the Canopy Walk only accessible by stairs, such as the Eagle’s Nest and the Tree House, the majority of the path is an ADA-accessible boardwalk, and we took my son on the walk in his stroller with ease.

Seek out the covered bridges

There are dozens of charming, historic covered bridges in Vermont, and the Woodstock area is home to several. 

Middle Covered Bridge is perhaps the most photographed, as it sits right in the center of downtown Woodstock, just off the Village Green.

a dark brown covered bridge sits at the end of a short lane

Surprisingly, this covered bridge is on the newer side, having been built in the 1970’s. Despite that, it looks just as historic as the many other bridges in the area.

a long red covered bridge spans a calm river on a sunny day in vermont

Head down Route 4 for a few miles and you’ll find the Taftsville Covered Bridge. This long red bridge, built in 1836, is an impressive 189 ft long. You can photograph it from a pull-off just down from the bridge. 

The enthralling Quechee Covered Bridge sits over rushing rapids. It’s a few minutes away from the Taftsville Covered Bridge. It’s located in—you guessed it—the town of Quechee! 

a brown wooden covered bridge sits over a rock sided river. a pine tree's branches border the image in the foreground

Take a Hike

a path through the woods in early fall

There are numerous options for lovely hiking near Woodstock VT. 

The majority of local hiking trails lie within the Marsh – Billings – Rockefeller National Historical Park. Yes, that’s right! There is a National Park in Vermont! 

This scenic property is home to miles of trails and carriage roads, offering opportunities for outdoor recreation in abundance.

Mount Tom is your #1 choice for a short yet very scenic hike. This peak will reward you with views over the town of Woodstock and the distant Green Mountains.

My friend Tara at Vermont Explored has a guide for an ideal easy to moderate hike of Mount Tom and the Pogue.

Want to get out and about for some hiking in the area? This resource for local hiking trails will tell you all you need to know.

You can also check out our article on the best Vermont hiking trails, for options near to Woodstock and farther afield. 

Experience Woodstock Vermont Fall Foliage

a classic farm scene in the fall, trees line a road leading to a farm with hills in the distance

Fall in Vermont is nothing short of epic, and towns like Woodstock are absolutely ideal for leaf-peeping fun!

There are so many great ways to get out and enjoy the beauty of the blazing Vermont fall foliage, whether you’re hiking, strolling downtown, or just going for a leisurely country drive!

Some of the outstanding things to do in Woodstock in the fall include:

  • Apple picking at one of the local orchards, such as Moore’s Orchards and Whitman Brook Orchard
  • A fall picnic atop Mt. Peg (a short, easy hike)
  • Day trip to nearby pumpkin patches & corn mazes

A Woodstock VT fall leaf-peeping trip is always a good time!

Enjoy the Ottauquechee River

a wide calm river fringed by spring and summer green, vermont

The Ottaquechee River brings this region together, and it’s something not to miss. Of course, you won’t really be able to since it’s right there!

One of the best ways to make the most of Woodstock’s pretty river is by sitting and relaxing on its banks. If you stay at a hotel located on the river, you’ll have a perfect spot to do so, as we did when we stayed at 506 on The River Inn,

Hop into one of those appealing Adirondack chairs and watch the world go by. 

Catch Some Classic New England Architecture

Covered bridges? Check! Stately Vermont homes? Check! White steepled churches? Check check check!

There’s no shortage of classic New England architecture in Woodstock Vermont.

A sign in front of a large white building surrounded by green trees in Woodstock Vermont
Some of the best Woodstock VT attractions are the many buildings featuring quintessential New England style architecture.

A walk around downtown Woodstock will introduce you to much of this quintessential architecture, but don’t just stick to the main road.

Venture off into the nearby residential areas. The stately homes are beautiful, and during one of my visits to Woodstock in July, the homes were draped with red, white, and blue banners and flying many American flags.

a classic white New England church

Classic New England at its finest!

As you explore Woodstock’s Main Street area, don’t miss a look at the iconic Woodstock Inn. The lawn and flowers in front of the inn are always a treat, and this is absolutely an example of quintessential New England charm. 

Hit the Slopes at Saskadena Six

Saskadena Six is one of the country’s oldest ski resorts, and it’s absolutely one of the best things to do near Woodstock VT!

Located just 5 minutes up the road in Pomfret, Saskadena Six is the place to go for outdoor adventures in summer or winter; play in the snow on the mountain while skiing or snowboarding, or embrace a Woodstock Vermont summer by participating in guided mountain bike tours, hikes, and more in this absolutely gorgeous outdoor space!

READ NEXT  The 10 Best Ski Resorts in Vermont

Visit Farmhouse Pottery

This Woodstock Vermont shop is America’s largest studio pottery workshop, and in addition to their stunning selection of pottery homeware, they also offer “Clay Dates” where you can handcraft your own piece right alongside a master potter. This would be a very unique Woodstock VT souvenir!

Check in With the Woodstock VT Events Calendar

If you’re looking for things to do in Woodstock VT this weekend or on any other specific date, be sure to check in with the Woodstock VT events calendar!

How else would you know that National Ice Cream Day is being celebrated at Billings Farm and Museum in July?

Places to Stay in Woodstock, VT

After a day spent adventuring around lovely Woodstock, what could be better than a wonderful spot to rest your head? There are plenty of great hotels in Woodstock, VT to choose from, and we have a couple of recommendations, depending on what you’re looking for.

The Woodstock Inn

If you’re looking for where to stay in Woodstock VT, consider The Woodstock Inn and Resort, an exquisite property that hosts beautiful weddings; the onsite spa is considered one of the best things to do in Woodstock VT to unwind!

A stay here is definitely more of a splurge, but it is a great option for a romantic getaway in Woodstock, VT. Click here to check the latest prices and availability.

Very large white building with an expansive lawn outside in Woodstock Vermont
If you’re looking for charming indulgence, Woodstock Inn and Resort is the Woodstock hotel for you!

The Jackson House Inn

Another one of the hotels in Woodstock Vermont you might choose is the Jackson House Inn. For those seeking a classic Vermont bed and breakfast experience, this is a terrific choice.

The inn is located a few miles from downtown Woodstock, providing a more country feel. Click here to check prices and availability.

The Sleep Woodstock Motel

Motel sign reading \
One of the best hotels Woodstock VT has to offer!

For the budget conscious, there can be no better choice than the Sleep Woodstock Motel. In fact, this is an all-around excellent option for hotels in Woodstock Vermont! The prices are reasonable, especially since the motel feels a bit upscale.

Sleep Woodstock is a newer addition to the Woodstock area, and it is a good one as this region doesn’t have too many budget-friendly accommodation choices. Clean, cute, and homey, the Sleep Woodstock has the vibe of a 1950s motor lodge combined with the touches of a modern hotel.

We were hosted here during our recent Woodstock stay, and we really, really loved it. The room was spacious, every feature was brand new, and the bed provided one of the most comfortable nights of sleep ever!

Our room had a fridge and microwave, too: very convenient for chilling our wine.

Smiling girl lying on a white bedspread in Woodstock Vermont
One of our favorite Woodstock Vermont hotels!

To top it off, the motel’s owner, Patrick, is super friendly and ready to give you tons of suggestions for things to do around Woodstock, VT, especially where to grab the best food.

We absolutely recommend Sleep Woodstock for couples, families, and other travelers. It’s an affordable motel in Woodstock, VT in a great location. Click here to check prices and availability.

Fat Sheep Farm

For a unique place to stay near Woodstock VT, consider Fat Sheep Farm in nearby Hartland, just about a 20 minute drive from Woodstock. Fat Sheep Farm is a working farm that also offers cozy cabins for rent on this sprawling 60-acre property. For a taste of working farm life- because yes, you do get to help tend to the animals!- there’s no better opportunity than a stay at one of the coolest places to stay near Woodstock!

Check out our experience at Fat Sheep Farm here!

Where to Eat in Woodstock Vermont

There are plenty of restaurants in Woodstock, VT that beckon you to try them. Unfortunately, you’ll never get to them all in a single visit, but you can get a good sample!

When time is limited, we recommend checking out these great restaurants in Woodstock:

Eat Farm-to-Table Goodness – Cloudland Farm

You can’t miss out on farm-to-table dining in VT. The state’s immense farmland has inspired countless restaurants that use crops, meat, and more straight from the source.

One Woodstock Vermont restaurant that should be on the top of your list is Cloudland Farm. This farm-to-table operation is absolutely divine.

Tables and chairs on an outside wooden deck in Woodstock Vermont
Take in the view from the deck at one of the restaurants in Woodstock Vermont

Cloudland Farm is found up a winding set of beautiful VT roads. The route is so woodsy that you might feel as if you’ve taken a wrong turn, but you’re on the right track. Around a final bend, you’ll see the sprawling property overlooking a stunning mountain vista.

Before your meal begins, you can sit on the veranda and simply take in the view with a glass of wine. It’s so relaxing and romantic. (Cloudland is BYOB, so plan ahead and bring along your favorite bottle of wine or a selection of beers.)

Then, it’s time for your dinner.

Get ready for an incredible meal. Each night’s menu is different, with chef-selected daily fare crafted entirely from local ingredients.

A list on your table tells you where each item has been sourced. Cloudland partners with an impressive number of farms in Vermont, New Hampshire, and even Massachusetts.

Gourmet dinner on a white plate in Woodstock Vermont
You can see here why this is one of the must-visit restaurants Woodstock VT has to offer!

The entree at Cloudland was braised pork (raised right at Cloudland itself), herb mashed potatoes, with a rhubarb compote and a berry glaze. Amy had a vegetarian option: risotto cakes, also with fresh rhubarb and a local egg.

Closeup of gourmet burger in Woodstock Vermont
When it comes to restaurants in Woodstock, VT, Cloudland gets a double thumbs up!

Both dishes were phenomenal, served with a fresh green salad to start and finished off with strawberry crepes and basil ice cream. The entire experience was lovely, and the food flavors were brilliantly paired.

The waitstaff is great, and your dinner feels personalized and special. We highly recommend Cloudland for fine dining in Woodstock, VT.

Coffee and Breakfast in Woodstock, VT – Mon Vert Cafe

As you may know, we really love coffee! Mon Vert has excellent coffee options in a hip downtown cafe. But it’s their breakfast that keeps guests coming again and again. Wow!

We dined on fruit-topped french toast and classic biscuits and gravy. We were stuffed to the gills after our meal, but we were so, so content.

French toast with strawberries and syrup on a white plate in Woodstock Vermont
French Toast in Woodstock VT? Yes, please!

The staff here is amazingly friendly and down-to-earth, something that can really take a coffee shop or restaurant to the next level. 10/10 highly recommend! 🙂

Like Cloudland, Mon Vert Cafe also relies heavily on local farms and suppliers. No doubt, this is one of the reasons the food is so awesome.

Historic dining room with large map on the wall reading \
Woodstock VT restaurants like Mon Vert Cafe offer that cute, small town experience!

Tasty Dinner in Woodstock – Worthy Kitchen

An amber liquid in a goblet that says \

Another of the best restaurants Woodstock VT has to offer is found a bit east of downtown.

In an unassuming brown building, you’ll find the delicious Worthy Kitchen, a super casual eatery that is often really crowded–and with good reason. This place is deeeelish.

We ate a Saturday night meal here and had a tough time choosing what to order. Eventually, Nathan opted for a brisket sandwich, and I went classic–a cheeseburger. Both were excellent and served with good fries.

Don’t miss the nice local beer menu, either.

More Vermont travel planning here:

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