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Harvard Yard fall foliage
Photograph: Courtesy GBCVB/Kyle KleinHarvard Yard fall foliage

Vermont's most photographed place closing during fall foliage

Sleepy Hollow will restrict access for tourists and influencers

JQ Louise
Tanya Edwards
Edited by
JQ Louise
Written by
Tanya Edwards

Picturesque Cloudland Road in Pomfret, Vermont, is sleepy and quiet for 11 months of the year. However, the past few autumns have seen the small road overrun with out-of-state tourists and influencers, trying to get the perfect photo in front of a beautiful farm. 

What’s Sleepy Hollow Farm?

Now, Sleepy Hollow Farm, the most popular address in Pomfret, is no longer accessible to tourists in the fall. The sleepy little town of Pomfret, which is near Woodstock, has 

approved road closures and parking bans around Cloudland and Barber Hill roads from September 23 to October 15. Just in time for leaf peeping – and fall photo taking – season. 

The incredibly picturesque, pastoral land component comprises 115 acres of fields, gardens, woods, trails, and two ponds, according to a recent real estate listing that priced the property at 2.5 million dollars. According to, the private property “is catnip for photographers. In the morning or early evening, the narrow road to the farm might be lined with as many as 20 cars, as shutterbugs hunker down with their tripods.”

Why is Sleepy Hollow Farm closed?

Neighbors of the farm recently launched a GoFundMe to raise money for additional police and signage in the area, and the page explains that  “Cloudland and surrounding roads become impassable during the fall, and roads and poorly behaved tourists have damaged roads, had accidents, required towing out of ditches, trampled gardens, defecated on private property, parked in fields and driveways, and verbally assaulted residents.”

“The last several years, there has been a significant increase in tourism interest in a particular private property on Cloudland Road,” Benjamin Brickner, a Pomfret select board member, told NBC 5

The farm has a gate and security cameras to try and deter people from trespassing, and apparently the pile-up of cars created a public safety concern. Emergency service vehicles cannot pass the narrow roads with cars parked and two lanes of traffic, so the town made the decision to close the roads.

When are the roads closed around Sleepy Hollow Farm?

The town of Pomfret has posted traffic restrictions between Sept. 23 and Oct. 15:

Cloudland Road south of Barber Hill Road will be closed to motor vehicles.

Barber Hill Road will be closed to eastbound motor vehicles.

Parking will be prohibited around the intersection of Cloudland Road and Barber Hill Road.

The restrictions do not apply to local residents in Pomfret and Woodstock, or their guests, contractors, and service providers, only to visitors. 

For other places to enjoy the foliage check out our fall foliage guide! 

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