Nestled in the heart of Vermont, along the coveted Cloudland Road, lies the enchanting Sleepy Hollow Farm. This pastoral haven, just a short ten-minute drive from Woodstock village, encompasses 115 acres of idyllic landscapes, including fields, gardens, woodlands, meandering trails, and two serene ponds. It's a place where nature's beauty meets historical charm.

Protected by the Vermont Current Use program and the Vermont Land Trust, Sleepy Hollow Farm has a rich history that stretches back to the late 18th century. The original farmhouse, constructed around 1790, serves as a testament to the area's enduring heritage. Over the years, the farmhouse has been thoughtfully updated and expanded, seamlessly blending the old with the new.

One of the property's highlights is a magnificent barn, a true equestrian's dream. This barn is not only home to six horse stalls but also features a tack room and a spacious, beautifully finished wood-paneled recreation room on its upper level. It's a space where modern comfort and rustic charm coexist harmoniously.

Sleepy Hollow Farm is more than a residence; it's a masterpiece of New England fall photography. The farm's iconic beauty has graced the lenses of countless photographers seeking to capture its timeless essence. The scene is straight out of a storybook—massive barns, a Cape farmhouse dating back to the late 1700s, and a magical play of light and shadow. During the autumn season, it's not uncommon to find the narrow road leading to the farm lined with as many as twenty cars, as photographers set up their tripods to immortalize this quintessential New England landscape.

However, the fame of Sleepy Hollow Farm has posed challenges for the local community. The surge in visitors, particularly during fall foliage season, has prompted temporary road closures along Cloudland Road to manage the influx of traffic. As of 2023, Cloudland Road will be closed to all visitors from September 23 to October 15. This closure will feature police enforcing the rules and this tactic was approved by both Woodstock and Pomfret town officials. The future holds questions about how best to preserve this cherished location for photography while respecting the needs of the local residents.

Sleepy Hollow Farm is more than a property; it's a testament to the enduring beauty of Vermont's landscape and a sanctuary for those who seek to connect with its rich history and natural splendor. The home last sold for $2.2 million on September 11, 2020. Prior to being sold, it was owned by Aerosmith guitarist Joe Perry and his wife, Billie.