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Sleepy Hollow Farm

Sleepy Hollow Farm in Woodstock, Vermont

Sleepy Hollow Farm in Woodstock, Vermont on October 10, 2020. Photo by Peter Stringer

Sleepy Hollow Farm in Vermont has become one of the most photographed fall foliage locations in New England, if not the United States, and for good reason. It looks like a painting come to life.

According to NewEngland.com, brothers Samuel and John Doten “left the family farm for a new life in central Vermont.” The brothers built neighboring farms, and the property has changed hands several times over the past few decades. Today, the iconic farm belongs to Aerosmith guitarist Joe Perry and his wife.

What makes Sleepy Hollow such a desirable photo location?

“You can shoot it from the road. It has this long, sweeping driveway that winds down to the property, giving you a perfect angle from above, of the barns and house. You’ve also got the ponds, which in the morning has mist coming off them and the hills behind it,” foliage expert Jim Salge told NewEngland.com. “In every possible way it’s perfect.”

While it wasn’t famous in the 90s, the last 10-15 years and the age of Instagram and camera phones have made it a popular spot. It’s not uncommon for the photo op to create traffic jams along Cloudland Road during peak foliage season. If your travels are taking you to Vermont, and specifically Woodstock, Sleepy Hollow is a must-see.

Note: Sleepy Hollow Farm is a private residence.

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Sleepy Hollow Farm, 3207 Cloudland Rd
Woodstock, Vermont 05091

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