Woodstock VT: Why You Can’t Miss This Famous Vermont Village

Woodstock is one of the most beautiful small towns to visit in Vermont! We recently made a trip here to explore the popular New England village and see what all the hype was about. Here are some of the best things to do in Woodstock VT and all about our experience. 

How to Get to Woodstock Vermont

The town of Woodstock is located in south-central Vermont in Windsor County and about a 20 minute drive from the New Hampshire border. The closest major bus and train station is in White River Junction 14 miles away. Here you can jump on a bus connection to Woodstock, but we wouldn’t recommend public transportation. ​

The best way to get to Woodstock VT is definitely to rent a car! Many travelers will fly into New York City or Boston, and pick up a rental car to make a road trip through New England. 

Your travels may also take you to Vermont’s largest city of Burlington where you can find plenty of vehicles available. There are many scenic routes to drive from Burlington, but the most direct is 1.5 hours on the I-89 South Highway.

We always use this website when searching for car rentals in the United States. It allows you to compare the different companies and rates to find the best deals! Here’s a quick breakdown of the distance between some of the most popular cities people fly in and visit Woodstock VT from.

Burlington VT: 90 Miles (1.5 Hours)

Boston: 140 Miles (2 Hours)

Montreal: 180 Miles (3 Hours)

New York City: 290 Miles (4 Hours)

Why is Woodstock VT So Famous?

The history of this town began in 1761 when the first European settlers arrived in bunches. In the late 18th century it would bring artisans and entrepreneurs to the area and become one of the largest villages in Vermont. Although that would dwindle out with large factories and mills coming into play, its artistry and local charm can still be felt today.

Woodstock has become known over the years as being not just one of the prettiest small towns in Vermont, but in the entire USA! The historic sites, stunning residential homes, and outdoor activities bring travelers in from all around the world. Truly, Woodstock Vermont is one of the best places to go for the quintessential New England experience. 

Yet, the real draw to this small town is the scenery during each of the four seasons. In springtime, the snow melts and flowers are in bloom. The summer brings amazing weather, special events, hiking trails, and a fun cafe culture. 

For many though, the best time to visit Woodstock VT is in the fall when the colors come alive. Autumn season brings the changing of the leaves which can be seen all over New England. Once the leaves come down in Vermont, the real fun starts! This is when you can take advantage of the many ski resorts just a short drive away. 

Our Visit to Woodstock Vermont

We made the trip to Woodstock VT recently on a beautiful September day. Jake is from Vermont originally, and it was actually along our route from Massachusetts to his hometown of Burlington! While we’ve spent a lot of time in Vermont, neither of us had ever been to Woodstock. 

The leaves were just starting to change and fall was in the air. This is our favorite season to be back on the east coast of the United States so it seemed like the perfect time to make our first visit to this popular town.

As soon as we arrived in the village of Woodstock VT we immediately fell in love. This quintessential New England town felt like something out of a movie! 

Old covered bridges, small cafes, and historic homes were everywhere we looked. It was easy to see why Woodstock Vermont is the perfect place for a day trip or weekend getaway. 

Where to Stay in Woodstock Vermont

When planning your trip to Woodstock VT, know that it is a very small town. This means that there aren’t a ton of places to stay. Most of the accommodations are bed and breakfasts that don’t have many rooms.

Be sure to book as far in advance as possible when you know your dates, especially in the summer and fall seasons! Here’s a few of the most highly rated places to stay in Woodstock Vermont. 

Woodstock Inn & Resort: Located right in the center of town and a quick walk from all the restaurants and cafes. The beautiful Inn has a cozy and welcoming feel with modern amenities. 

The Vesper Woodstock: This cute family-run bed and breakfast has vibrant decor and is the perfect home away from home. Enjoy being within walking distance to everything you need and all the best things to do in Woodstock VT.

506 On the River: Just outside of town, this inn is a great option if you want to be a little more out in nature. As the name suggests, it’s set right on the river and has a large indoor pool that’s open year round. 

Best Things to do in Woodstock VT

Woodstock Vermont Village Walk 

One of the very best things to do in Woodstock is simply stroll through the center of town. We particularly love the morning time here as the cafes are open and full of life. Pop in and out of the small artisan shops and pick up some Vermont maple syrup and other souvenirs to take home with you. 

Also, be sure to check out the Middle Covered Bridge which is probably the most photographed spot in Woodstock VT. Stretching out 139 feet over the Ottauquechee River, this unique spectacle is one of Vermont’s longest covered bridges.

Billings Farm & Museum

Just outside of the main part of town is one of the best museums and local farms in Vermont. Spread out over 200 acres, you’ll find a working dairy farm, gorgeous old barns, and nature trails. We highly recommend this activity for families with young kids. 

This is also a fun place to grab an ice cream at the Farmhouse Cafe and get some dairy products to take with you. If you enjoyed Billings Farm & Museum you may also want to take a trip to the Sugarbush Farm as well.

Skiing in Woodstock VT

With so many great ski resorts just a short drive away from Woodstock Vermont, many travelers use the village as a hub for their activities in the winter months. The closest to town is called Saskadena Six and is only a 5 minute drive in nearby South Pomfret. It may be small, but the trails are nice and it’s one of the oldest ski resorts in America!  

If the 3 lifts at Saskadena Six aren’t enough to scratch your skiing or snowboarding itch, be sure to check out larger resorts like Killington and Okemo. Cross-country skiing and snowshoeing are popular as well, and in the summertime many of the trails are used for mountain biking.

Marsh-Billings-Rockefeller National Historical Park

Did you know Woodstock is home to Vermont’s only National Park? That’s right! The nature paths are perfect to view the changing of the leaves in the fall, and you can even take a guided tour the historic mansions on site.

We’d previously visited gilded age Rockefeller mansions in Newport Rhode Island, so this was such a nice change of pace! The start of the Mount Tom trail is also found within the park. This 5.5 mile round trip will take you high above for epic views of the town.

Enjoy a Local Meal in Woodstock VT

We hope you’re hungry on your visit to Woodstock VT! The town is home to many amazing restaurants and a fun cafe and bar scene. If you have time, make sure to also visit the Long Trail Brewery which is located just 10 minutes away in Bridgewater Vermont. Here are a few of the best places to eat and drink in Woodstock.

• Lincoln Inn & Restaurant At The Covered Bridge
• Simon Pearce
• Mont Vert Cafe
• Melaza Bistro
• Worthy Kitchen
• Richardson’s Tavern

Is Woodstock Vermont Worth Visiting?

Yes! Whether you’re just passing through this part of the state or looking for a fun weekend trip, Woodstock VT is totally worth it. The great thing is that it’s small enough where you could see it in just a couple of hours.

However, to really experience it you should stay overnight for a couple days in this unique New England town. From the covered bridges and nature trails to the local artisan’s shops and food, there are so many fun things to do in Woodstock Vermont! 

Have any questions about this article or want to share more of your favorite things to do in Woodstock VT? Leave us a comment below! 

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USA Travel Planning 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip! 

Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Sea Cave Kayak Tour in La Jolla California! 

 Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials! 

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