Vermont’s Very Own Woodstock Is One of the Country’s Best Small Towns to Visit

It's no surprise that Woodstock, Vermont, is lauded as the best small town in the Green Mountain State. With a population of approximately 3,000 residents, it's the ultimate place to experience quintessential New England. Woodstock is located in the southern part of Vermont, in Windsor County. Aside from being known as a friendly little locale, Woodstock is an ideal destination for a day trip, too. There's so much to experience when you visit—from strolling through the town center and admiring unique architecture to the jaw-dropping natural beauty and impressive food scene.

In our experience, this is one of the best towns to visit in Vermont, and one trip is all it will take for you to quickly agree. If you're curious about Woodstock, read on to learn more about why this small town is one of the best in Vermont!

Because Woodstock is in the southern part of the state, it's a convenient destination for a day trip or weekend getaway from New Hampshire, Massachusetts, and New York.

From the moment you arrive, you'll notice that the town is filled with undeniable charm. To get the most of your time there, we would recommend getting out into the country along the dirt roads. You will feel miles away from the rest of the world and get lost in the rolling hills of the pristine countryside. A Trip to Sugarbush Farm is a must.

The neighboring town of Quechee is equally charming, and both places boast flowing waterfalls and historical covered bridges. In our experience, we have yet to find a place that embodies Vermont's charm quite like this part of the world.

Architecture enthusiasts will also find a lot to love about Woodstock. Walking through town, you'll stumble across some fascinating and historic buildings, like Our Lady of the Snows Church, located at 7 South Street.

The Marsh-Billings-Rockefeller National Historical Park offers several beautiful trails to explore and gardens. If you are anything like us, then the Jersey Cows will be a delight to see grazing in the field near the visitor's center with the mountains as a pretty backdrop.

In the fall, the Sleepy Hollow Farm is known as one of the most photographed farms in New England. However, due to the increase in visitors on this narrow dirt road, the town closes the road from September through October and only allows local traffic. But don't worry—there are plenty of other places to admire fall in Vermont. Just be mindful of local traffic!

Another must-see spot is the Taftsville Covered Bridge. This bright red bridge has a mighty flowing river under it and makes for some fantastic photo ops. We love that you can take a short path down to the water and explore the rocks and shoreline underneath this historic bridge.

And, if you need to be reminded of why Woodstock is the best small town in Vermont, simply spend some time by the Ottauquechee River.

One of the best places to explore this natural beauty is to take a trip to Quechee and visit the Quechee Gorge State Park. Witness the sheer power of this mighty river in what is known as "The Grand Canyon of the East," or hike down to the water and go for a swim on a warm summer day.

So, do you agree that Woodstock is the best small town in Vermont? After traveling the state, we can say this is one of the best towns to visit in Vermont. We love the historic charm and the natural beauty found in the farmlands, mountains, and countryside. If you haven't been to this little town, make sure you plan a trip!

Feeling inspired? Try planning your own trip using Only In Your State’s itinerary planner.