Quiet Time for Vermont’s Sleepy Hollow Farm

Following road closures, Vermont’s iconic Sleepy Hollow Farm and its neighbors get a much needed reprieve from fall foliage tourists.

By Ian Aldrich

Sep 12 2023


Sleepy Hollow Farm in Pomfret, Vermont (Captured in 2018)

Photo Credit : Mark Fleming

A note from the editors: In light of the unprecedented number of visitors in recent years and road closures, we ask that this fall you please enjoy the many existing photos of the property, and direct your efforts instead to the many wonderful foliage sights and activities in and around the Woodstock area.

Throughout the year, Sleepy Hollow Farm in Pomfret, Vermont, is a destination for photographers. But in autumn it becomes something else completely.

If you have even a passing interest in New England fall photos, you’ve no doubt already seen pictures of the property. Located just outside the all-things-autumn town of Woodstock, Sleepy Hollow sits off Cloudland Road, a winding dirt road lined by stately maples and restored farmhouses. With its big barns, late-1700s Cape farmhouse, and knack for catching the light just right, Sleepy Hollow is catnip for photographers.

But in recent years its celebrity has grown to unmanageable levels, putting a severe strain on both the road and Sleepy Hollow’s neighboring residents. Just ask Michael Doten, who lives across the street from the farm and whose family has owned property on Cloudland for several generations

“It’s just become such a mad house,” he told Vermont’s local NBC affiliate. “Especially around the Indigenous People’s Day holiday weekend. It just gets crazy. We’ve counted over 100 cars at any given time parked alongside the road. It just creates a major traffic jam.”

At other times, the inconveniences have been much worse. “Increasing traffic has caused safety, environmental, and quality-of-life problems — blocking roads to residents and emergency vehicles, leaving trash and damaging private property, making noise at early and late hours, flying drones over homes, and trespassing through photo shoots on lawns, driving, picnicking, and parking on hay fields, and harassing livestock,” Pomfret Selectperson Ben Brickner told the Vermont Standard in June.

As morning sunlight begins to spill into the valley, photographers jockey for a shot of Sleepy Hollow Farm in South Pomfret, Vermont. (Captured in 2018)
Photo Credit : Mark Fleming

Something had to be done and so this year Pomfret and Woodstock got proactive and passed a measure to close Cloudland and neighboring Barber Hill roads from September 23 through Sunday October 15 to non-residents. The Windsor County Sheriff’s Department will enforce the ban.

This isn’t the first time officials have tried to manage Sleepy Hollow’s celebrity draw. Last year, the Pomfret highway department erected signs to establish the road as a one-way lane. But traffic jams and the throngs of photo taking tourists still came. Will this year’s ban make a difference? Sleepy Hollow’s neighbors are hopeful.

“[It will] probably what I used to consider a normal foliage season,” said Doten. “We’ll have traffic. We’ll have some people coming through and looking and slowing down. But we won’t have hordes or people hanging on the gate of my neighbor’s property.”


The History of Sleepy Hollow Farm

Things to Do in Woodstock, Vermont