February 8, 2023
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What’s So Awesome About the Sleepy Hollow Vermont Farm?

Sleepy Hollow Farm in Woodstock, Vermont

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The Sleepy Hollow Farm in Woodstock, Vermont (Pomfret, VT) was founded in 1780 by two brothers, Samuel and John Doten.

They ran their family farm until 1780 when they left for Vermont. There’s where they started logging which became their new company. The farm has been in operation for over 200 years.

They were not the first to do so, their land was chartered in 1761 and a few years later they became its first settlers. Nine years after this, the village was named Pomfret. Over the next few years, some locals from Durkee’s hometown followed him and settled in. They called this place New Pomfret, but it got shortened to just Pomfret.

The Doten brothers, John and Sam, moved to Vermont and built farms next to one another. John built his farmhouse on a piece of land with views of the hills.

Over the next century and a half, both Doten families continued to use both farms. There were few, if any boundaries between these two properties. They were connected by pastures, where family members from both farms would play and work together.

In the 1950’s, the family decided to quit farming after years of hard work at the Sleepy Hollow Farm

Woodstock, Vermont is a place of natural beauty and rural charm. One of the many attractions in this picturesque town is Sleepy Hollow Farm. This working farm offers visitors a chance to see life on a real Vermont farm.

The former farm, which would come to be well known as Sleepy Hollow, transferred to a few different owners during those next decades.

Once owned by Aerosmith guitarist Joe Perry, (who purchased it in 2005, later selling it in 2015), Joe loved the nature Vermont is so well known for.

“Vermont definitely turned me on to a lot of things,” Perry told the Burlington Free Press in a phone conversation from his home in Massachusetts. “When you’re learning any kind of art you pick things up from anybody who’s doing it, whether they’re really good at it or learning like you are. Vermont was definitely what I needed.”

“I like that not much changes there” in Vermont, Perry said. “I like the politics there. I truly believe if it had been another time in history it would be its own country. I like the people there. I like the freedom there, the openness. And it’s beautiful.”

The Sleepy Hollow Farm in South Pomfret, Vermont is one of the most photogenic farms in the state of Vermont.

It’s located close to the village of Woodstock which makes it easy to reach by car, yet still very secluded. It is located off Cloudland Road and has become a mecca for photographers and site seers from around the world. The farm and the surrounding area are private, but you can still take some nice pictures from outside. best angle is from the no entry sign. Please be respectful. Make sure you park on the sides of the road, without blocking traffic, and leave place once pictures are taken out of respect for others who might be taking photos. Also, please heed no trespassing signs and leave the area clean and undisturbed.

Listed for sale in 2020, the property sold in September, 2020 for $2,200,000. The property is conserved both in the Vermont Current Use program and by the Vermont Land Trust. A variety of photos can be viewed here.

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