In search of the best things to do in Woodstock, VT?
I am here to steer you in the right direction!
I’ve spent lots of time in Woodstock during the 15+ years I lived in Vermont. I adore this classic, beautiful Vermont town and in fact, Woodstock is my #1 recommendation on where to visit in Vermont if you’re looking for the classic New England experience.
In this travel guide, I’m going to share with you 20 fun things to do in Woodstock, Vermont, including some terrific places to eat, some fun things to do with kids, and the most scenic sites in the region.
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.
Table of Contents
When is the Best Time of Year to Visit Woodstock VT?
When is the best time to visit Woodstock, Vermont?
The first question many Vermont visitors ask is “when should I visit Woodstock?”
Fortunately, Woodstock is beautiful in all seasons. Although late winter and what is sometimes called “stick season” here in Vermont is admittedly less magical.
But fall and winter are probably the standouts for most visitors, and I agree!
Woodstock has consistently been named one of the best places to visit at Christmas and one of the most beautiful towns in America.
It consistently tops list of Vermont fall foliage locations not to be missed. People adore fall in Woodstock, with all its color and charm.
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 western border of New Hampshire.
How To Get to Woodstock, VT
To get to Woodstock, you’ll need a 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 offering the most flight options.
With these travel basics, you can start planning the perfect Woodstock getaway.
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!
The Best Things to Do in Woodstock VT
Experience Woodstock Vermont Fall Foliage
Let’s start with something everyone wants to know: what is there to do in in the fall in Woodstock? The answer: PLENTY!
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!
Important Note for 2023!
You may have seen in other guides for things to do in Woodstock or in countless influencer images on Instagram, a certain photogenic farm recommended. This is called Sleepy Hollow farm and in recent years has gained extreme popularity.
Unfortunately, the popularity has gone too far. This farm is private property and situated on a small country road. Sadly, the inundation of tourists trying to catch a glimpse of the farm has created a number of issues, including major traffic concerns on this residential road. There has also apparently been many instances of visitors trespassing on the property and being disrespectful of this property as well as neighbors’.
In 2023, residents of the area have worked together to close this road to the public during the height of fall foliage season. So, please do not attempt to visit Sleepy Hollow Farm this fall. And even when the road is reopened, I would strongly discourage you from visiting. Instead, please consider visiting one of the many public, local farms that would welcome you! These include Sugarbush Farm, Billings Farm, and others.
And PS: while Sleepy Hollow is scenic, there are literally thousands of gorgeous properties in Vermont you could see with the same beautiful autumn magic. So go drive down some back roads and explore a bit. And remember, always respect private property.
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.
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.
I loved meeting the animals at this farm
Stroll America’s Sweetest Downtown
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.
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:
- Unicorn – unique gifts and novelties
- Yankee Bookshop – Vermont’s oldest running independent bookstore
- Vermont Flannel Company – stay cozy!
- 37Central Clothiers
- Red Wagon Toy Co.
Even if you’re not shopping, I recommend just taking a walk around in downtown Woodstock VT. 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.
Experience a Classic Woodstock Vermont Christmas
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
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 includes 95 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 and The 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
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.
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.
I recommend checking their schedule before your visit. There are various programs and demonstrations throughout the day that may catch your interest, so you’ll want to plan around those.
Sift Through Endless Antiques
New England is a great place to go antiquing. I’m 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!
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. I especially liked the 1791 Cocktail, which had a fruity touch.
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 to Woodstock is a less than 15 minute drive!
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.
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.
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.
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.
Trust me: get their Vermont cheese soup! Drool!
If you time your meal right, you might be lucky and get one of the tables overlooking the tumbling water outside!
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.
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.
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.
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.
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.
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.
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.
Take a Hike
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.
Enjoy the Ottauquechee River
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 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.
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!
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 I 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.
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
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.
My husband and I were hosted here during one of our trips to Woodstock, 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.
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.
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.
The entree at Cloudland was braised pork (raised right at Cloudland itself), herb mashed potatoes, with a rhubarb compote and a berry glaze. My husband had this, while I had a vegetarian option: risotto cakes, also with fresh rhubarb and a local egg.
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.
My must-order item whenever I visit Mon Vert is a maple latte. Bliss.
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.
Tasty Dinner in Woodstock – Worthy Kitchen
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:
- 10 Top Spots for Cross Country Skiing in Vermont
- 12 Fun Things To Do in Brattleboro VT
- Top 12 Fun Things to do in Killington VT
- 13 Best Places to Stay in Killington VT: Where to Stay in Killington
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Amy Hartle is the founder and Editor-in-Chief of New England With Love, a comprehensive resource for travel in the New England region. Amy has been exploring New England since 2001. She lived in Vermont for many years and is a graduate of Plymouth State University in New Hampshire. On this site, Amy aims to share her love of New England and help you to have the best possible adventures!
Amy has been writing about travel for over a decade, and is a full time blogger, publishing both Two Drifters and Let’s Adventure Baby. When not traveling the world or creating epic blog content, Amy can be found cuddling with her husband, son, and cats, & drinking a maple latte.