It is one of the most iconic farmsteads in the world…
This is the real life Sleepy Hollow Farm located in Pomfret, Vermont.
But how did this historic farm in rural Vermont become one of the most photographed places in New England?
Situated on 115 pristine acres of rolling pastures and woodlands, Sleepy Hollow Farm has been in existence since the original Cape farmhouse was built in the late 1700’s. But it has only become a photographers’ dream destination since leaf-peeping vacations in New England became a thing along with the of the rise of photo sharing sites like Instagram. Thanks to many appearances on scenic calendars, Sleep Hollow Farm has become ubiquitous with all things autumn.
You’ve probably seen it on your Facebook feed a few times a year in the fall.
It also doesn’t hurt that the name ‘Sleepy Hollow’ is the name of a favorite Halloween tale about the infamous Headless Horseman in The Legend of Sleepy Hollow by Washington Irving.
A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.– Washington Irving, “The Legend of Sleepy Hollow”
Sleepy Hollow sits off Cloudland Road, a winding, narrow dirt road lined by thickets of maple trees and old farmhouses. Photographers love it for the barns and the way the morning or early evening light catches the rolling hills surrounding the group of rustic buildings.
In the late 1780s, two brothers from Connecticut, Samuel and John Doten, left their family farm for a new life in central Vermont. The brothers each built their own farm on connecting plots of land.
The farms stayed in the same family for many generations until the 1950’s when the Sleepy Hollow farmstead was sold off to other owners.
Notably, the picturesque farm was most recently owned by Aerosmith guitarist Joe Perry and his wife, Billie, who used Sleepy Hollow as their Vermont retreat.
It was listed for sale in 2020 and actually sold in September, 2020 for $2,200,000.
The property includes the original 1700’s Cape house and a heated six-stall barn with a loft/studio that is connected to the house, as well as two ponds, an historic school house/guest house and a log cabin that rests on a ridge with fantastic views of the surrounding hills.
Let’s have a look in the historic Cape first:
It’s been thoroughly renovated to modern standards but it still maintains some original features such as exposed support beams, wide-plank wood floors, and some of the original fireplaces.
The kitchen:
Dining room:
Den/office:
Bedrooms:
In the photo (below) from the listing, we get a glimpse into the life of the famous guitar-playing former owner:
Now let’s have a look at that amazing barn!
Here’s the loft/studio recreation space:
And the very clean and beautiful horse stalls:
It is an amazing spread but House Crazy Sarah’s favorite part of the property is the historic one-room school house which has been converted into a guest house.
It still kinda has the old schoolhouse feel to it!
Last but not least, is the log cabin.
Interestingly, the property was offered for sale complete with an array of motorized vehicles including a tractor, UTV and ATVs with wheels and tracks, two dirt bikes, and a diesel-powered snowcat groomer, according to the listing.
The land of the Sleepy Hollow Farm is conserved both in the Vermont Current Use program and by the Vermont Land Trust so no matter who owns it, it will always be preserved.
Sources:
Newengland.com/today/travel/vermont/the-history-of-sleepy-hollow-farm
Snyderdonegan.com/listing/4779987/3429-cloudland-road-pomfret-vt-05067/
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