33 Fun Things to do in Woodstock, Vermont in 2023 

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If you are traveling to Vermont this year (or next) and unsure where to make home base, look no further than the beautiful town of Woodstock. As one of the most charming towns in the state, Woodstock, Vermont, is a must-stop destination on any New England road trip. With its idyllic covered bridges, historic homes, country stores, and breathtaking natural beauty, Woodstock offers visitors a perfect escape from the hustle and bustle of city life. 

Woodstock is a treasure trove of history, culture, and outdoor adventure, making it a destination worthy of anyone’s travel bucket list. There are many ways to enjoy every season in this year-round town, from scenic drives, local markets, cultural festivals and more. Fall is stunning in Woodstock but also crowded. I’ve visited in fall and summer and both seasons are a joy. While I highly recommend a fall visit as the beauty of the rolling hills, picturesque farms, and charming streets truly transform into eye-popping colors, don’t count out summer or winter for a magical experience in their own right.

There are many fun things to do in Woodstock and the surrounding areas, you’ll find it easy to fill a long weekend with activities, but a day trip is also enough time to see the highlights and enjoy a bite at a local cafe. Read on to discover 33 of my favorite things to do in Woodstock, Vermont.

Bookworms unite at the Bookstock Festival

If you are visiting in June, Woodstock brings together lovers of the written word through Pulitzer Prize-winning speakers, poets, and authors during a weekend-long community event on the Village Green called the Bookstock Festival. Enjoy live music, exhibits, shopping, and a highly anticipated rare book sale annually at the end of June.

Taste of Woodstock

If you are more into food and wine head to Woodstock in August for the annual Taste of Woodstock festival. This community event ties together the local community with local business showing off the best of Vermont. With live music and over 50 vendors showcasing everything from beer, wine, maple syrup and arts and crafts, the entire family will love this event.

Enjoy Farm Fresh food, Cider and Wines at Fable Farm

More than just a farm, Fable Farm Fermentory strives to protect local farmland while promoting local business and elevating the community through specialized events. Delving into ciders, wines and fresh farm to table foods a visit to the farm just 20 mins outside of Woodstock is one of the best things to do while visiting Woodstock. Fable Farm hosts many events through the year including Feast and Field, a Thursday night gathering complete with live music, cider, wine and freshly prepared food from the farm.

Try local maple syrup at Sugarbush Farm 

Looking for a taste of authentic farm life in Vermont? Look no further than Sugarbush Farm in Woodstock! This working dairy farm gives visitors a chance to experience the simplicity of local farm life while also enjoying some of the best local products around.

If you’re a foodie or nature lover, Sugarbush Farm is one of the best things to do in Woodstock, Vermont. This family-run farm is renowned for its delicious maple syrup and locally crafted cheese, which you can sample during your visit. Don’t forget to try the award-winning maple syrup, tapped from the farm’s own maple trees- several grades and flavors are available. You can even walk through the maple woods to view the tree-tapping process!

Sample local flavors at Cloudland Farm

Cloudland Farm offers a must-visit dining experience near Woodstock! Cloudland has farm-to-table dining and raises laying hens, Angus beef, turkeys, pastured pigs, herbs, and vegetables, so this is a great place to sample the local flavors. You can also purchase local cheeses, maple syrup, Vermont soda, pottery, and more at the onsite market.

You will find incredible eats at this local farm, and the Appalachian Trail runs right through it, so be sure to bring your hiking boots!

Marsh-Billings-Rockefeller National Historical Park  

Marsh-Billings-Rockefeller National Historical Park truly captures the essence of American conservation history. This national park encompasses beautiful historic homes, lush forests, and well-tended gardens, offering an enchanting blend of natural beauty and human-made charm. 

As you wander the scenic nature trails, you’ll be surrounded by the legacy of the three influential families that lived on this land – the Marsh, Billings, and Rockefeller families – whose conservation efforts and love for the environment are integral to the park’s existence today. 

The first resident of this land was George Perkins Marsh, one of the first conservationists in America. Later, it was the home of Frederick Billings, and then his granddaughter, Mary Rockefeller. This museum is on the National Register of Historic Places, so history buffs will love it!

Get up close to farm animals at Billings Farm and Museum 

The picturesque Billings Farm and Museum is located along the charming Old River Road in Woodstock, Vermont. Established by Frederick Billings in 1871, this scenic working farm has become a delightful destination for visitors of all ages. Home to a herd of beautiful Jersey cows and a variety of other friendly farm animals (yes – you can pet them!), Billings Farm provides an immersive and educational experience for those eager to learn about traditional farming methods and rural life. 

As you wander through the lush fields and historic barns, you can’t help but be captivated by the rich history and serene atmosphere that this extraordinary farm and museum provide. 

Snap a photo at idyllic Jenne Road Farm

In the picturesque town of Reading, Vermont, lies the stunning Jenne Road Farm, a true New England gem. Just a 15-minute drive from Woodstock, Jenne Road Farm boasts an incredible landscape – and holds the title of the most photographed farm in Vermont (especially in the fall!). With its quintessential red barns, vibrant green pastures, and idyllic country setting, it’s no wonder visitors from far and wide can’t resist capturing the beauty of this 460-acre farm. 

Pro Tip: The best angle of the farm is from Jenne Rd. with the gravel road in the foreground. I didn’t realize this until after my visit, which I was thinking to myself, this isn’t that great. I will definitely be back during the fall to snap another photo from a better perspective than the one above. It really is a beautiful setting, especially in fall.

Hike up Mount Tom 

At a height of over 1,300 feet, this stunning mountain is located within Marsh-Billings-Rockefeller National Historical Park. If you are an experienced hiker, getting to the top will take about a half hour.

Two trails climb Mount Tom – the first is an easy climb from behind the mountain, and the other is a faster route that begins in the center of Woodstock. You can find the easier path on Route 4; turn right after the Farmer’s Market. The quicker (but more difficult) trail starts at the park on Mountain Avenue, just behind the covered bridge. Whichever path you choose, the views from the top are absolutely breathtaking!

In the winter, Mount Tom transforms into a winter wonderland, providing an excellent opportunity for Nordic skiing. This mountain is a popular spot for day hikes in the summer and fall due to the beautiful weather and stunning views.

See rare plants in the Eshqua Bog Natural Area

The perfect place to visit to relax and appreciate the tranquility of nature. Described as a hidden floral treasure, it is free to access and hosts and array of cold-tempered plants from orchids and fen plants to cotton grass and larches. All can be seen from the flat boardwalk. Plan a visit during late June to see the hundreds of pink Lady Slipper Orchids in bloom. There is only parking for a few cars, but the boardwalk is not long so be patient of waiting on a parking spot to open up.

Explore Downtown Woodstock

Downtown Woodstock is a vibrant culture, history, and natural beauty hub. Located along the Ottauquechee River, this neighborhood is ideal for those seeking a quintessential New England experience. With its charming main street, bustling town center, and stunning surroundings, Woodstock Village offers a warm and welcoming atmosphere for visitors of all ages.

Take in some fresh air at the Village Green

One of the main attractions of downtown Woodstock is the Village Green, a beautifully maintained park in the center of town. This inviting space is surrounded by an array of gift shops, general stores, ice cream shops, and delicious food stops, making it the perfect place to enjoy the local offerings. Be sure to stop by “The Green” for the weekly farmers market in the summer or fall.

Enjoy the activities at the Woodstock Inn and Resort

If you’d like to stay near downtown while visiting Woodstock, check out the iconic Woodstock Inn and Resort. This historic and luxurious retreat offers exceptional accommodations, fine dining, and a myriad of recreational activities, all set against the backdrop of lovely Vermont scenery. Whether you’re indulging in well-deserved pampering at the spa or hitting the links on the award-winning golf course, the Woodstock Inn and Resort promises an unforgettable experience.

Take in some solitude at the Norman Williams Public Library

If you’re a book lover, you’ll want to visit the Norman Williams Public Library in Woodstock Village. This historic institution, founded in 1883, houses an extensive collection of books, periodicals, and archives and a welcoming space for community events and gatherings. Lose yourself in the pages of a great novel or attend an engaging lecture, all within the stately walls of this beloved cultural landmark.

Grab a bite at Mon Vert Cafe

For an authentic taste of Woodstock’s culinary scene, visit Mon Vert Cafe, an organic eatery and coffee shop in the heart of the village. With a menu that boasts fresh, seasonal ingredients and a focus on sustainability, Mon Vert Cafe is one of the best places to refuel after a day of exploring downtown.

Drive under the Middle Covered Bridge 

Another gem in downtown Woodstock is the Middle Covered Bridge. This charming wooden structure spans the Ottauquechee River and provides a picturesque setting for leisurely strolls and photo opportunities.

Enjoy the Woodstock History Center

Celebrating the evolution of Woodstock, the history center is located in a historic home in the heart of downtown Woodstock. It’s open in summer and fall, usually closing in mid-October. Entry is free, and exhibits are filled with historic collections of photographs and artifacts depicting the evolution of Woodstock. The beautiful garden in the back lawn has lovely views of Woodstock’s only covered bridge, Middle Bridge.

Enjoy the Woodstock Arts Festival

The annual Woodstock Art Festival transforms the village green into an art lovers paradise the weekend after Labor Day. Enjoy booths with over 30 artists displaying their talent and creativity, offering portraits and prints, along with farm to table food and local spirits.

Have a family day at the Vermont Institute of Natural Science

The Vermont Institute of Natural Science (VINS) is one of the best places near Woodstock, Vermont, for nature enthusiasts and families alike. This environmental education center is dedicated to fostering an appreciation for the natural world through engaging exhibits, interactive programs, and exciting wildlife encounters. 

One of the standout features of VINS is its spectacular Forest Canopy Walk, which gives visitors an immersive and thrilling experience high above the ground. This elevated walkway winds through the treetops, providing a unique perspective on the forest ecosystem and allowing guests to truly connect with nature. With an elevated treehouse, a human-sized spider web 43 feet above the ground, and a replica of an eagles nest, this is a great spot for the entire family.

Photograph the Taftsville Covered Bridge

With its distinctive red color and lattice-style trusses, the Taftsville Covered Bridge is both an architectural marvel and a picturesque attraction. Built-in 1836, this historic bridge spans the Ottauquechee River, providing both a functional crossing and a scenic viewpoint for locals and visitors alike. After being carefully restored in 2013 following damage from Hurricane Irene, the bridge has regained its former glory and continues to serve as a vital link between Woodstock and Taftsville. 

A wooden covered bridge surrounded in green trees.

Drive under the Lincoln Covered Bridge

Constructed in 1877, this wooden structure spans the Ottauquechee River, providing visitors and locals with a delightful journey through time. As you cross the bridge, marvel at the wooden Pratt truss construction, one of the only known examples in the world. It’s not as picture-perfect as the Middle covered bridge or Taftsville bridge but for architectural enthusiasts, this is one of the best things to do in Woodstock, Vermont. 

Go fishing in the Ottauquechee River 

Running through eastern Vermont, a visit to the Ottauquechee River is one of the best things to do in Woodstock, Vermont, for nature lovers and adventure-seekers alike. This enchanting gem begins in the eastern slopes of the Green Mountains, inspiring visitors with its mesmerizing beauty and abundant opportunities for outdoor recreation. Stroll the Ottauquechee River Trail, a 2.5-mile path with lovely views of hills, fields, woodlands, and the river. 

While this river isn’t the best spot for kayaking due to its shallow waters, it is a great place to go fishing as it is home to plenty of trout.

Go for a refreshing dip in a local Swimming Hole

There are many swimming access points along the Ottauquechee River in Woodstock Village all offering their own unique views and experiences. For views of Middle Covered Bridge, head to the access point near the Woodstock History Center. For a more secluded experience, follow the hidden path next to Elm Street Bridge, it is even deep enough to jump into the river from the large boulder. If you are looking for a spot great for small children, enjoy the sandy beach and waist-deep water at the access point between the Woodstock Recreation Center and the Little Theater or head down to Silver Lake State Park and have fun on the soft sandy banks of Silver Lake.

Sleepy Hollow Farm (Elm Grove Farm)

This quaint, family-owned farm offers a serene atmosphere surrounded by lush green pastures, rolling hills, and stunning fall foliage that New England is famous for. Located in Pomfret, Vermont, Sleepy Hollow Farm is nestled off Cloudland Road. You’ll notice stunning maples and restored historic farmhouses along this dirt road, making this area especially lovely for an autumn drive. 

While this is a private farm, you will see many photographers and on lookers lined up along the surrounding dirt road, hoping to catch the perfect shot of the red barn and 18th-century Cape farmhouse. But with the beautiful rolling hills and colorful foliage, who can blame them? If you decide to drive past this farm, don’t forget to bring your camera!

Sleepy Hollow is one of the most popular places to capture a fall photo as the crowds during peak fall foliage show. Please respect the property, do not go beyond the driveway gate and only park legally. There may be new parking enforcement forbidding parking along Cloudland Road. Check out this IG Reel I made showing what the crowds can look like during fall.

Admire the talent at the Simon Pearce Flagship Store 

Nestled along the banks of the picturesque Ottauquechee River, just 12 minutes outside the charming town of Woodstock, Vermont, is the Simon Pearce Flagship Store. This store location offers an exquisite selection of handcrafted glassware and pottery and a breathtaking view overlooking the iconic Quechee Covered Bridge. As you explore the store’s elegant pieces, marvel at the skilled artisans demonstrating their glassblowing techniques right before your eyes. 

You can also grab a bite to eat at the onsite restaurant – sit outside for a fantastic view of the waterfall dam and covered bridge. Menu favorites include shepherd’s pie, quiche, and refreshing cocktails.

Rent a Mountain Bike

Woodstock, Vermont, has several mountain biking trails, including the Aqueduct Trails, Mount Peg Trails, and Saskadena 6 Trails. The Mount Peg Trails and Aqueduct Trails both feature 9 miles of single-track trails, and Saskadena 6 has a 4-mile trail network. Don’t forget to check trail conditions before you go!

Take a Guided Bike Tour

With pleasant weather, gorgeous scenery, and plenty of interesting stops, Woodstock, Vermont, is perfect for exploring via bicycle. Enjoy a biking tour with Discovery Bicycle Tours – from great food to luxurious accommodations, they’ll plan your entire journey!

Discover a thrilling adventure with New England Falconry

This one-of-a-kind adventure offers you the chance to get up close and personal with some of the most majestic birds of prey, including falcons, hawks, and even owls. The friendly, knowledgeable, and passionate staff can guide you through a hands-on, interactive demonstration, where you’ll learn about the history of falconry and the vital role these extraordinary birds play in our ecosystem. The New England Falconry is one of the best things to do in Woodstock, Vermont, for animal lovers!

Walk through Elm Arches 

This charming sculpture garden provides visitors with an inspiring experience as they explore the unique, whimsical sculptures scattered among the lush greenery. This perfectly curated landscape features meandering pathways beneath stately elm trees, creating a sense of enchantment as you discover each carefully placed artwork. From abstract sculptures to wooden arches you can walk through, Elm Arches has something for everyone’s artistic taste.

Learn the art of pottery at Farmhouse Pottery

Farmhouse Pottery is where old-world charm meets modern-day craftsmanship. This delightful gift shop and workshop provide visitors with an unforgettable experience as they learn the art of pottery from skilled artisans passionate about their craft. With a strong focus on sustainability and supporting local communities, there’s no better place to stop for a pottery class!

The Calvin Coolidge Memorial Homestead 

Nestled in the picturesque town of Plymouth, Vermont, just a short 20-minute drive from Woodstock, you’ll find the Calvin Coolidge Memorial Homestead. This historic site once served as the childhood home of America’s 30th president. As a well-preserved homestead, this site offers visitors a unique glimpse into the early 20th-century rural life that shaped one of our nation’s most humble and hardworking leaders. 

As I strolled through the grounds, I really enjoyed its lush green landscapes, rustic buildings, and friendly farm animals. Inside the homestead, you’ll be transported back in time with rooms filled with original furnishings and personal artifacts that vividly depict the Coolidge family’s day-to-day life. 

Old Constitution House 

Located in the charming town of Windsor, Vermont, just a short 30-minute drive from Woodstock lies a hidden gem of American history – the Old Constitution House. This unassuming yet significant site is where the first constitution in the United States to abolish slavery was adopted in 1777, paving the way for Vermont’s statehood. With fascinating exhibits, like a tap room, tea room, and parlor, visitors can learn about the historical events that took place here and the remarkable individuals who shaped the state’s future. 

Justin Morrill Historic Homestead 

Situated in Strafford, VT, the magnificent Justin Morrill Historic Homestead is just a 34-minute drive from the picturesque Woodstock. This beautifully preserved architectural gem is a testament to the life and work of Justin Smith Morrill – a self-taught architect, prominent US Senator, and the driving force behind the Morrill Land-Grant Colleges Act of 1862. As you step onto the serene grounds of the homestead, you’ll be transported back in time to the 19th century in this Gothic Revival-style masterpiece.

Spend the day at Silver Lake State Park

If you love nature and being on the water, this state park makes the perfect day trip. For a small $5.00 fee, enjoy fishing, swimming and other water sports like kayaking and paddle boarding during the summer months with picnic areas and shaded shelters. Silver Lake becomes a popular spot for ice skating and fishing in winter. Tent camping and RV sites are available for a weekend get-a-way. What makes this park extra special are the Park Interpreters who lead creative and educational activities, including, night hikes, arts & crafts, campfire programs, and amphibian discoveries throughout the month.

Take a day trip to charming Stowe, VT 

Just a little over an hour away from Woodstock, Stowe, Vermont, is a charming destination with a variety of activities. Start your day by strolling through the quaint village center, filled with general stores, art galleries, and delectable eateries. Be sure to grab a coffee and a bite to eat at one of the cozy cafes before embarking on an outdoor adventure and snapping a photo at the Welcome to Stowe mural in downtown. 

Surrounded by stunning mountain views, Stowe is a haven for nature enthusiasts, offering nature trails, mountain biking, and even zip-lining. If you’re visiting during the colder months, hit the slopes at the renowned Stowe Mountain Resort for some skiing or snowboarding fun. Don’t forget to indulge in a bit of relaxation with a visit to one of the many spas in the area, offering rejuvenating treatments and picturesque views. 

Go hiking in Groton State Forest

If you’re looking for a fun-filled day trip amidst the beauty of nature, Groton State Forest in Plainfield, Vermont is the perfect destination! Just a 1.15-hour drive from Woodstock, this state park offers a fantastic escape from the chaos of daily life. 

Owls Head

One of the must-visit spots in this forest is the Owls Head area, where you can embark on a 1.8-mile hike and immerse yourself in the lush greenery and picturesque surroundings. As you ascend, you’ll be rewarded with breathtaking views of the surrounding landscape. Don’t forget to bring your camera to capture the stunning panoramas from the top!

Nichol’s Ledge

Another fantastic hiking spot within Groton State Forest is Nichol’s Ledge, located 1.30 hours away from Woodstock. This steep 0.6-mile hike takes you through the forest, leading you to a lovely viewpoint overlooking a lake. It gets busy, and there is no official parking along this dirt road, so be respectful of the area and neighbors when looking for a space to pull over.

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I hope you enjoy your time in Woodstock as much as I do. I always make it a point to at least drive through the town while enjoying a New England Road trip. It is truly one of my favorite small towns with so much personality!

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Sam wearing backpack and hat walking through town.

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2 Comments

  1. I am planning a trip back to the Adirondacks this fall, and found your 7 day itinerary most helpful in my planning. I am hoping to come back to Canada via the Finger Lakes, and wanted to include a visit to Cooperstown, and Saratoga on my way through. Do you have any information on these two towns? Thanks. Donna

    1. Samantha Stamps says:

      Hi Donna, I’ve never spent time in Saratoga and only a few days in Cooperstown in my teens. Sorry I do not have information on them but the Catskills region is close to Saratoga and another fantastic spot for fall foliage!

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