Sleepy Hollow Farm

(9 reviewss)


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

9 reviews for Sleepy Hollow Farm

  1. Tom Riley (store manager)

    I LOVE Sleepy Hollow Farm. I visited in Feb 2018 and it was a spectacular spot. I’ve heard it gets busy in the fall, but luckily no one was there when I visited. I can’t wait to return soon!

    Image #1 from Tom Riley
  2. Ron Hall

    Sleepy Hollow Farm

    Image #1 from Ron Hall
  3. Periece

    I can see why this is a popular photography spot!

    Cool fact: Did you know Aerosmith Guitarist, Joe Perry used to own the the famous Sleepy Hollow Farm in Pomfret, VT!?

    Image #1 from Periece
    Image #2 from Periece
  4. Cristina

    The Sleepy Hollow Farm in Pomfret Vermont

    Image #1 from Cristina
  5. Fulla Brazil

    The cutest farm. 🍁

    It looks like you’re about to enter a whole magical world. ✨

    Image #1 from Fulla Brazil
  6. Nilay Kant Singh

    Sleepy Hollow Farm

    Image #1 from Nilay Kant Singh
  7. Brett Abraham

    Sleepy Hollow Farm in Vermont

    Image #1 from Brett Abraham
  8. Lauren Bender

    Sleepy Hollow Farm

    Image #1 from Lauren Bender
  9. Patrick

    Sleepy Hollow Farm, Vermont

    Image #1 from Patrick
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