11 Best Things to Do in Woodstock, VT (Family Friendly)
Are you planning your family getaway to Woodstock, VT, and wondering what are the best things to do during your family getaway? You are in the right place.
We visit Vermont at least once yearly to escape busy city life and experience complete serenity. It is five hours from New York City, making it a perfect long weekend getaway. I am sharing some of the best things to do here, the best places to eat, and where to stay.
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Best Things to Do in Woodstock, Vt
1. Stroll through Main Street and Explore Shops
Woodstock, Vermont, is known for its beautiful downtown, filled with various artisan shops, galleries, and cafes. You will also spot a famous Middle Covered Bridge here.
When you visit Woodstock, VT, strolling through the main street is a must-do.
The variety of shops, from boutique clothing and home decor to gourmet food and specialty gifts, caters to different interests and needs.

Some of my favorite shops in Woodstock, Vermont, include:
F.H. Gillingham & Sons: A historic general store serving the community since 1886, it features various goods, including groceries, gifts, Vermont-made products, kids’ toys and games, etc. You can easily get lost here with so many options around. I highly recommend checking.

The Vermont Flannel Company: This shop is a must-visit for cozy apparel. It is known for its high-quality flannel clothing and accessories.
Yankee Bookstore: If you love books, you will love this bookstore. It offers a curated selection of books and other items, including vinyl records. The shop is known for its unique charm and commitment to serving readers from Vermont and beyond.

2. Check Out Covered Bridges
Vermont is known for its covered bridges, which reflect its rich history and architectural heritage.
These bridges are typically wooden and feature a roof that covers the span, protecting the wooden components from the elements.
They were primarily built to provide safe passage over rivers and streams when transportation infrastructure was less developed.
The Middle Covered Bridge stands out for its historical significance and aesthetic appeal, making it a must-see for anyone visiting the area.
It is located directly on the main street, so it is almost impossible to miss it once you are there. Take a walk and enjoy the views of the Ottauqechee River from the bridge.

3. Hike Mount Tom (Faulkner Trail)
The Faulkner Trail, located near Woodstock, Vermont, is a beautiful hiking path that leads to Mount Tom. It is about 2.8 miles long and is known for its gentle switchbacks, making it accessible for hikers of various skill levels.

As you hike, you’ll gain about 530 feet in elevation, which adds a bit of challenge but is manageable for most people.
The trail is mainly well-maintained, and the final stretch offers a stunning panoramic view of Woodstock and the nearby mountains from the summit.
The hike starts with well-maintained switchbacks, which are lovely for walking with kids and enjoying the beautiful forest.
As we hiked up more, it got steeper and rockier before we reached our first lookout (Not the main summit view)

We reached the viewpoint where we decided to stop and enjoy the peacefulness.
From here, there is just one last challenging ascent to the main summit area, which is a bit rocky and has hand railings.
We were uncomfortable climbing the last ascent with kids, and we ended up hiking back down, but overall, we enjoyed the trail and would highly recommend it to anyone looking for an easy to moderate challenging hike in Woodstock, Vermont
4. Visit Billings Farm and Museum
We love visiting Billings Farm and Museum in Woodstock, Vermont! It’s a perfect spot for families!
This charming place lets you step back and experience life on a 19th-century farm. You can meet adorable Jersey cows, friendly draft horses, and many other cute animals.

The beautiful scenery and historic barns make it a lovely place to explore together. The tractors outside, of course, were a big hit for boys.

Billings Farm and Museum offers a variety of educational activities, including farm activities and crafts, designed for different age groups.

During our last visit, they demonstrated how butter is made. It was an inspiring program that allowed kids to get a hands-on experience and taste crackers with freshly made butter!

5. Visit SugarBrush Farm
We only recently discovered Sugar Brush Farms, and I loved it. I wonder why we haven’t visited it before.
Sugarbush Farm is a charming family-owned farm known for producing high-quality cheeses and pure Vermont maple syrup.
We started our trip at their little playground, which was directly by the parking area. The kids were obsessed with it. The farm was very thoughtful! You will also find a small animal barn close to the playground.

Next, we explored the Maple Tree Trail. Here, you will find maple trees with holes and metal spouts for extracting the syrup. The educational part of the visit is for both kids and adults.

The next and most exciting stop here was visiting the gift shop. I warn you that it will be tough to leave it empty-handed with so many cute and delicious things offered. So expect some spending.

We bought some maple syrup and a souvenir to bring with us, which I am pleased about.

Overall, Sugarbush Farm is a delightful destination for anyone interested in Vermont’s culinary traditions. It offers a unique blend of education, delicious food, and beautiful scenery.
6. Hang out By Ottauquechee River
If you’re planning a trip to Woodstock, Vermont, in warmer months, you must spend some time by the Ottauquechee River!
This beautiful spot is perfect for relaxing and soaking in the natural scenery. We spent our early morning here before heading to explore the farms, and the sound of the river was so calming. The kids also enjoyed throwing rocks in the water.

7. Marsh-Billings-Rockefeller National Historical Park
The Marsh-Billings-Rockefeller National Historical Park combines conservation history with natural beauty.
As you explore the park, you will discover lush landscapes and historical buildings that played a pivotal role in land stewardship in America.
The mansion, with its elegant rooms and art collections, offers guided tours that delve into the lives of the Marsh, Billings, and Rockefeller families.
Walk through the carriage roads and woodland trails to experience the serene environment they worked to preserve. The park is also home to educational programs focused on environmental sustainability and history.
8. Vins Forest Canopy Walk
The VINS Forest Canopy Walk is a must-visit attraction at the Vermont Institute of Natural Science (VINS) in Quechee, Vermont. This unique elevated walkway takes you high above the ground, allowing you to explore the forest from the treetops.
As you stroll along the canopy walk, you’ll get a close-up view of the diverse wildlife and plant life that thrive in the forest. It’s not just a fun experience; it’s also educational! The walk provides insights into the importance of forest conservation and the habitats of various species.
Perfect for families and nature lovers, the VINS Forest Canopy Walk offers a memorable way to connect with nature and learn about the environment. Don’t miss this opportunity to see the forest like never before!
Woodstock is a charming town with plenty to offer, but sometimes you might want to explore further.
Things to Do Near Woodstock Vt
9. Quechee George Trail
Visiting the Quechee Gorge Trail near Woodstock, VT, is a fantastic outdoor adventure for nature lovers and families.
The trail is about 1.3 miles long and offers stunning views of the Quechee Gorge, often called Vermont’s “Grand Canyon.” You’ll be treated to breathtaking scenery as you hike, including dramatic cliffs and the rushing Ottauquechee River below.
The trail is generally considered easy to moderate, making it accessible for all skill levels. Along the way, you’ll find plenty of spots to stop and take photos or enjoy the peaceful surroundings. Whether looking for a stroll or a more challenging hike, the Quechee Gorge Trail is a must-visit destination showcasing Vermont’s natural beauty.
10. Take a Day trip to Stowe, Vt
If you’re looking for a perfect day trip from Woodstock, head to Stowe! Beautiful mountains surround this charming town, famous for its stunning scenery, especially in the fall when the leaves change color.
You can stroll down Main Street, where you’ll find cute shops and delicious restaurants. If you love the outdoors, there are plenty of hiking and biking trails to explore. And don’t forget to stop by the Ben & Jerry’s factory for a tasty ice cream treat!

11. Visit Hanover NH
A quick trip across the state border, Hanover is home to Dartmouth College.
You can explore the beautiful campus, visit the Hood Museum of Art, or enjoy dining and shopping in the quaint town.
Best Places to Stay in Woodstock, Vermont
When visiting Woodstock, Vermont, you’ll find various delightful accommodation options to suit your needs.
Woodstock Inn and Resort: This historic inn offers elegant rooms, a spa, and an on-site restaurant. You’ll be right in the heart of town, making exploring easy.
506 On The River Inn: This family-friendly option features spacious rooms, an indoor pool, and beautiful river views. Kids will love the on-site activities, and you’ll appreciate the peaceful setting.
The Blue Horse Inn is a charming bed and breakfast with individually decorated rooms and a welcoming vibe. It’s a short walk from downtown, providing easy access to shops and dining.
Where to Eat in Woodstock, VT
Here are some fantastic spots if you’re looking for a memorable meal in Woodstock, Vermont.
The Ransom Tavern: This restaurant in the Kedron Valley Inn features an authentic Italian menu. You’ll love the salads and pasta dishes, and there is an excellent selection of wine, craft beer, and cocktails.
Mont Vert Cafe: This cafe serves fantastic breakfast burritos and challah French toast, which are perfect for breakfast, and I still cannot get over how delicious my pesto sandwich was for lunch. The place also offers various coffee and smoothie options.


This cafe gets very busy, especially during peak seasons like foliage. To avoid long lines, arrive early as it gets busy by 9:30 AM.
The Worthy Kitchen: Worthy Kitchen in Woodstock, VT, is a popular farm-to-table restaurant known for its vibrant atmosphere and delicious comfort food. The menu features a variety of locally sourced dishes, including mouthwatering burgers, fresh salads, and creative appetizers,


Abracadabra Coffee: Abracadabra Coffee, located in Woodstock, Vermont, is a specialty coffee roaster known for its focus on single-origin coffees and a vibrant atmosphere. Here are some key highlights about Abracadabra Coffee:



Abracadabra Coffee prides itself on sourcing high-quality, single-origin beans from various regions worldwide. It emphasizes ethical sourcing and sustainability, ensuring its products are delicious and responsibly produced.
Woodstock Scoops: The shop offers various flavors, including classic favorites like vanilla and chocolate, and unique options like maple creemees, peanut butter, raspberry, key lime, and more. It often features seasonal flavors and unique creations.

Woodstock Farmers Market is a great spot for families looking for fresh, local food. The market features a deli with sandwiches, salads, and picnic options. Kids can enjoy exploring the market and trying local treats.

FAQs: Things to Do in Woodstock, Vermont
A quick trip across the state border, Hanover is home to Dartmouth College.
You can explore the beautiful campus, visit the Hood Museum of Art, or enjoy dining and shopping in the quaint town.
What are the top activities to enjoy in Woodstock during the winter season?
In the winter, you can explore cross-country skiing at the Mount Tom trails or enjoy ice skating at the Union Arena Community Center.
Which attractions should I not miss when visiting Woodstock in the fall?
Don’t miss a hike to the top of Mount Tom for stunning foliage views. Also, visit the Marsh-Billings-Rockefeller National Historical Park to see vibrant autumn colors and billings and the Farm and Museum.
Are there unique shopping experiences in Woodstock, and where can I find them?
Woodstock is home to charming boutiques and galleries. Woodstock Farmers’ Market and F.H. Gillingham & Sons offer local goods and unique finds.
What are the most recommended places to stay when visiting Woodstock?
Consider staying at the Woodstock Inn & Resort for luxury accommodations or at 506 for a family-friendly stay.
What makes Woodstock a worthwhile destination for travelers?
Woodstock’s rich history, scenic landscapes, and vibrant local culture make it a perfect getaway. From hiking and skiing to shopping and dining, there’s always something to enjoy.
Whether you’re a foodie or a nature lover, Sugarbush Farm has something for everyone. At this beloved local spot, enjoy the charm and flavors of Vermont.
Best Time to Visit Woodstock, Vt
Woodstock is charming all year round, and while there are plenty of activities each season, nothing compares to a foliage season, specifically September to October, when the little town is transformed into a colorful paradise.
If you wish to visit during peak foliage, you must book your accommodations as early as possible and expect prices to increase since demand is usually very high.
Woodstock in Fall
Autumn in Woodstock brings a spectacular fall foliage display that attracts visitors from near and far. As the leaves change, driving along the scenic Route 4 or hiking up Mount Tom provides some of the best views.
Early October is usually the peak time for vibrant colors.
Stroll along the Marsh-Billings-Rockefeller National Historical Park, where you’ll find a mix of hardwoods and evergreens.
Woodstock Wassail Weekend
Vermont’s Wassail Weekend is a beloved holiday tradition that takes place in the picturesque town of Woodstock.
Typically held in early December, this festive event transforms the village into a winter wonderland with twinkling lights and holiday decorations.
Visitors can enjoy various activities, including carriage rides, craft fairs, and live music. One of the highlights is the Wassail Parade, where the community comes together to celebrate with floats, carolers, and the famous “Wassail,” a warm, spiced drink. It’s a beautiful time for families and friends to gather, enjoy the holiday spirit, and create lasting memories in this charming Vermont setting.
Conclusion: Things to do in Woodstock, Vt with Family
Here you have it. Our favorite things to do in Woodstock Vt which are also family-friendly!
Woodstock, Vermont, is a fantastic place for families to explore and have fun together. Start your adventure at Billings Farm & Museum, where kids can enjoy interactive exhibits and learn about farm life. For some outdoor fun, hike the scenic trails on Mount Tom, which offers beautiful views for everyone to enjoy.
Don’t forget to visit Sugarbush Farm, where you can see how cheese and maple syrup are made. Take a leisurely walk across the historic main street and enjoy a beautiful stroll with shops and restaurants.
With its mix of nature, history, and hands-on activities, Woodstock is sure to create wonderful family memories!
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