Thousands of flannel-clad visitors flock to Sleepy Hollow Farm every autumn for an Instagram photo op, creating a dangerous nuisance for the town and local residents.
By Ethan Weinstein, VT Digger
Amid social media-induced traffic jams, the towns of Pomfret and Woodstock plan to close roads this fall leading to a popular foliage photo op.
Pomfret’s picturesque Sleepy Hollow Farm has featured in films and magazines for years. The property’s winding driveway leads downhill past a small pond to a weathered barn and farmhouse, backed by grassland and a wooded hillside. Photographers tend to congregate on the road looking over and above the Disney World version of Vermont.
But town officials say that since the advent of social media, hundreds of cars and thousands of tourists now flock to the dirt road every fall.
“It’s always been a popular foliage tourist destination, attraction, whatever you want to call it,” said John Peters Jr., chair of the Pomfret Select Board. “People post and then everybody sees it. And then everybody wants to come see it.”
Thousands of TikToks and Instagram posts — many garnering tens of thousands of likes — have tagged the location of this photogenic hill farm.
A scan of those videos and photos shows tourists adorned in pumpkin spice-kitsch: flannels and big hats, earth tones and maple leaves abound. Many crank the saturation, turning the fall foliage to Day-Glo.
The pilgrimage to Sleepy Hollow has become so popular, a new genre of post has emerged, with people uploading videos contrasting their expectation of the property with the snapshot-hungry horde they actually find congregating at the farm. Others have taken to explaining that Sleepy Hollow is private property and will be closed to tourists this fall.
Last year, in an attempt to address traffic woes, Pomfret experimented with making Cloudland Road one-way only during peak foliage. But cars continued to park haphazardly along the narrow road, blocking driveways and through-traffic in the process. Despite no-trespassing signs, visitors regularly strolled onto private property, officials have said.
So this year, Pomfret and Woodstock agreed to access around Sleepy Hollow Farm from Sept. 23 to Oct. 15, with exceptions for locals, agricultural equipment and emergency vehicles.
Pomfret’s Select Board has also approved temporary signage and movable barriers to aid the traffic changes and has asked the Windsor County Sheriff to help enforce the restrictions under the town’s existing contract with that department.
Minutes from the August Select Board meeting during which Pomfret approved the measure show some residents expressing concern that the traffic restrictions favored some residents over others and set a worrying precedent. Ultimately, the board unanimously approved the decision, adding an amendment that allowed all town residents to use the roads, rather than just those who live in the affected area.
According to Peters, Pomfret won’t spend outside its approved budget to implement the fall traffic changes. A neighborhood group led by Cathy Emmons, co-owner of Cloudland Farm, a restaurant and farm on Cloudland Road, may help fund further enforcement measures, Peters said.
While the sheriff’s department will have the ability to enforce restrictions through tickets, Peters said the goal wasn’t to issue fines, adding that he wasn’t aware of any parking tickets given in no-parking zones on the road last year.