Sleepy Hollow Farm, one of Vermont’s most iconic properties, is located on desirable Cloudland Road, just 10 minutes from Woodstock village. The pastoral land component is made up of 115 acres of fields, gardens, woods, trails, and two ponds. The property is protected by the Vermont Current Use program as well as the Vermont Land Trust. The original farmhouse, built around 1790, has been updated and expanded, and now connects to a newer, fabulous barn with 6 horse stalls, a tack room, and a large finished wood-paneled recreation room upstairs. There are two other large barns nearby with workshops, garages, and storage. A small cabin with bunk beds and a wood stove is located next to the large second pond. The home is privately owned and most recently sold for $2,200,000 on 09/11/2020.
If you have even a passing interest in New England fall photography, you’ve probably seen images of this farm. Sleepy Hollow is a photographer’s dream, with its massive barns, late-1700s Cape farmhouse, and knack for capturing the light just right. The narrow road to the farm may be lined with as many as 20 cars in the morning or early evening in the fall, as photographers hunker down with their tripods. Avoid visiting in the fall if you want to avoid navigating through a sea of photographers and sightseers.
Looking for more great spots to explore in Woodstock, Vermont? Check out these 15 Most Beautiful Places In Woodstock, Vermont!
- Address: 3429 Cloudland Rd
- Town: Pomfret/Woodstock
- State: Vermont
- GPS: Lat 43.65805 Lng -72.50722
- Parking notes: When it comes to parking at the iconic Sleepy Hollow Farm, most people pull over on the side of Cloudland Road. It is important to respect the private property and to only take photos and view it from the road. It is best to simply drive by the farm and to not park. During the fall, parking is extremely hard to find.
- Parking directions: HERE
- Location directions: HERE