Get Lost
Imagine not being able to get into your driveway because there are too many photographers milling around. Now imagine that the reason you can’t get into your driveway that is overrun with photographers is not because you are dating Taylor Swift, but rather that your property has committed the crime of being too beautiful. Or, more precisely, it is considered one of the most scenic, idyllic, cover-of-Yankee Magazine-ready places in the region with its near perfect compositional elements and annoying habit of looking stunning in every season, nearly every light condition, and in any kind of weather. This is the curse of Sleepy Hollow Farm in Pomfret, Vermont.
Sometime in the 1780s, brothers Samuel and John Doten left their family farm in Connecticut to make a new life in the lush countryside of central Vermont. This seems a little like getting out of the navy to take a job on a Carnival cruise ship, but maybe even in the 1700s traffic around Hartford was a royal pain in the tuches. The brothers bought up a ton of property and built neighboring farms. Samuel’s house sat up on a hill that overlooked incredible vistas all the way over to the nearby town of Woodstock. John tucked his new digs right below. How this whole situation has not been made into a FOX sitcom starring Kenan Thompson and Damon Wayans I have no idea! Both of the brothers’ farms remained in the family, passed down through generations for over 150 years. By the 1950s the Doten Farms cycled out of the family and into the hands of various owners throughout the decades. One of the more recent owners was Aerosmith guitarist Joe Perry and his wife, Billie, who used the property as their Vermont “retreat” as one does.
The Perrys sold Sleepy Hollow Farm in 2020. It currently consists of 115-acres of fields, gardens, woods, trails, and two ponds all unfolding against a backdrop of gently rolling tree-lined hills that riot with color in the fall. A serpentine driveway plunges from the top of the road to the original Cape-style farmhouse built in the 1700s and upgraded with all modern conveniences. There is also a six-stall heated barn with a studio loft connected to the house as well as a guest house and log cabin—the kind of life that matches this property sold separately.
For years people made their way to Sleep Hollow Farm to photograph it in every season, but especially during peak foliage usually in early October. Fall is a DEFCON 1 situation in New England (you can read about that here). That’s not an exaggeration. As October sets in tour buses full of “leaf peepers” clog the roads and hog up to five perfectly good parking spaces. There is something that happens to people when the trees turn from green to the technicolor lightshow of reds, yellows, and oranges. We lose our damn minds. I think it’s a lot like what happened at Studio 54 whenever they’d drop something from the ceiling—glitter, balloons, cocaine—your surroundings go from zero to spectacular in a matter of moments and it’s almost sensory overload. It’s Dorothy stepping out of her sepia-toned house into the pop art palette of Oz. To be unaffected by the display is sound evidence that you are one of those party novelty cardboard cutouts.
The acceleration and proliferation of social media put Sleepy Hollow Farm on the map in more ways than one. Even at daybreak you could expect to find a handful of photographers clustered around the top of the driveway, vying for space with their tripods, or elbowing in with their giant lenses thrust at the collection of houses that looked like they belonged in a model train set up below. The farm is on Cloudland Road (real name, not rejected titles of the Virgin River spin-off series), which is a steep, narrow dirt road. More than one car pulled off to the side is enough to slow traffic in both directions. Add to this a bunch of bad practices like littering, trespassing, creating noise pollution, flying drones around the property, and generally disrespecting the area because the fundamental principle of humanity is that we can’t have nice things and people gotta moron. This year the owners and neighboring people living on the road decided they reached their limits; they petitioned the town to close the road to through traffic-#bummer.
I made my first and last pilgrimage to Sleepy Hollow Farm in 2018. I went on a mild day in early November so the trees were largely barren. But I had seen so many beautiful photographs, so many artful captures that I wanted to witness this scene in person. I wanted to wave my photo around on Instagram, feeling smug that I had journeyed to the heart of picturesque autumn and returned with the grail. God, would Ansel Adams been this insufferable working in the social media age? #onehundredpercent
I parked closer to the start of the road and wandered up to the farm. I was the only one there. I stayed on the road shooting. It was nice, but unsatisfying. And that had nothing to do with the skeletal trees or the watery near-winter light. “Beauty everywhere” is my mantra. It was that the scene was too “perfect.” And as our Lady Shania of Twain spoketh: “That don’t impress me much.” I had seen it depicted so much, so often and admired other peoples’ images, I expected to be knocked over by my own “wow!” just from being there in person. Instead I struggled to find that zing of energy I get when I stumble upon something uniquely interesting to my eye. Sleepy Hollow Farm—it’s not you, it’s me.
I lingered a bit taking a few more images from the road near the top of the driveway. By now two young girls had also wandered over. One was wearing some kind of wide-brimmed straw hat (#fallvibes) and they were both taking selfies and posing with duck lips and flashing peace signs and I felt mortally embarrassed for all of us. A car had been parked at the house and I noticed two women get in. The car crested to the top of the drive. The woman driving looked like she was in her early-70s; a young woman around college age was in the passenger seat. The driver rolled down the window and shouted: “This is private property!”
“I’m sorry,” I said. “I thought it was acceptable to photograph from here.” I was sincere. I felt terrible, conveyed by the “not all photographers” tone in my response. The woman scowled (I can still feel that scowl. If that was Joe Perry’s mom—damn, Joe. Your mom does not play!) and shook her head, driving away. The Instagrammers appeared unfazed entirely, crouching down to get more of the farm in their filtered shots or TikTok video. And that was a wrap to my lackluster Sleepy Hollow experience.
While some photographers on social media expressed their dismay, but ultimate understanding that the farm would be out of reach for the season, I was glad. The people on the road deserve their peace and privacy, of course. And I think it’s a blessing in disguise, freeing people from the lemming mentality we’ve perfected of following the trail of viral breadcrumbs instead of discovering what moves us on our own. The road not taken means you might get lost and that could make all the difference. Magic is wherever you find it, not where it’s manufactured. #truth
Lens Zen!
Happy haunting season! A lot of neighborhoods really amp up the pumpkin pressure. Not even super spies are immune to keep up with the Spooky Joneses.
Ugh, influencers.
Beautiful words and pictures as always! I'll be honest, I was expecting something spooky given the Sleepy Hollow name. Glad everyone you encountered still had their heads about them. :)
Okay, enough pleasantries. I was so excited to see the return of my favorite Soviet spies! I want a story about them, mkay? Shh: tell no one!
“And I think it’s a blessing in disguise, freeing people from the lemming mentality we’ve perfected of following the trail of viral breadcrumbs instead of discovering what moves us on our own.”
So much this! I’m also with you on the disappointment when my expectations have been pushed so high that nothing can meet them. There are so many cool things to do in the world, let’s find joy in our own ways instead of going off of the popular lists all the time.