Vermont’s Very Own Woodstock Is One Of The Country’s Best Small Towns To Visit
By Marla S.|Updated on October 18, 2023(Originally published August 10, 2021)
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Marla S.
Author
Marla is a professional writer with experience creating content such as blogs, newsletters, web copy, and marketing materials for her clients in the travel, health, and education industries.
Previously, Marla had lived and or traveled to over 35 countries. She's also called Boston, New York, San Francisco, and Brattleboro, Vermont home. Aside from taking every opportunity to explore the globe, Marla also enjoys spending quality time with her dog, learning languages, and working on her novel.
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, Woodstock is the ultimate town in Vermont to experience quintessential New England. Woodstock is located in the southern part of Vermont, in Windsor Country. Aside from being known as a friendly little locale, Woodstock is an ideal destination for a day trip, too. When you visit, take a stroll through the town center and check out some unique architecture on the side streets. Plan to explore some of the tourist sites like Sleepy Hollow Farm and spend time by the river during your visit, too. 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.
The town is filled with undeniable charm and 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. Visit the tiny church on the property, walk through the maze of maple trees being tapped, and visit the farm animals (we loved seeing Happy the cow). No trip to this farm is complete until you try the maple syrup and some of the best cheese we have ever tasted.
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Experience life like a local when you stroll through the town's center and browse in the shops.
The neighboring town of Quechee is equally as charming and among the two places, you can find stunning dams with flowing waterfalls right in town and historical covered bridges. In our experience, we have yet to find a place that represents Vermont in all its charm quite like this part of the world.
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As you walk through town, you'll stumble across some interesting architecture, like the Our Lady of the Snows Church. You'll find this unique church 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 of visitors down this narrow dirt road, the town closes the road from September through October and only allows 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 and it is especially gorgeous in the fall. For more about this region of the state check out this Adventuring in the Moment video.
Don’t forget anything you need while packing for a trip with our ultimate road trip packing list.
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