Dover Stone Church, Our Gateway to New York’s Abandoned History

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As the fall laid down a blanket of leaves and blazed in glorious colors, it seemed a strange time to leave New England, but New York state is a magnificent bastion of historical references all rolled into one endless sweep of stunning terrain. And it’s just over the Connecticut border, where a place called Dover Stone Church opened a doorway into New York’s abandoned secrets.

What Is Dover Stone Church Exactly? Well, It’s Not a Building

We set off on a drizzly grey morning, leaving central Connecticut behind for brighter skies and the promise of no rain. As we traveled west, gaining in altitude through the western hills, there was indeed a brightening of the sky. The fine mist faded as well, leaving us with a rolling cover of taupe colored clouds sporting white underbellies.

Crossing the border into New York State, we chatted about a million things, horses, Ali’s new barn that was under construction in Oregon and many other mother-daughter tidbits of information shared on road trips like these. From the back seat, Nemo watched our progress, impatiently awaiting our arrival. If there is one thing this Golden Retriever understands, it’s when we’re heading out on a great adventure.

Dover Stone Church is definitely that. Framed by a gothic arch carved delicately by Mother Nature’s hand, the small stone cathedral is no manmade mausoleum. Instead, it rests peacefully within the confines of the Taconic Mountain range, hiding treasures that have ensnared visitors throughout the ages.

Gothic Adventure Awaits at Dover Stone Church Preserve

Some have likened it to the fantasy world of J.R. Tolkien’s hobbits and elves. For us, it seemed more of a medieval adventure, leading us toward the dragon’s lair and the newly constructed bridge guarded by trolls.

A GPS search for Dover Stone Church Preserve took us directly to the trailhead where no-parking signs guarded the entrance, just as you’d expect for the lair of a mythical beast. Fortunately, this is the 21st century, and Google makes it easy to find unmarked parking when visiting a dragon’s den, so we quickly learned that we had two options: the nearby elementary school or Frescho 22 Plaza.  Neither were far away, but with school in session, we chose the latter.

Fall proved an advantageous time to visit Dover Stone Church Preserve. The trail entrance is lined with trees. Even on a dim autumn day they glowed crimson as we descended the stairs to pick up the Dover Stone Church trail.

young woman and golden retriever walk a colorful tree-lined path to Dover Stone Church
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We passed through the neon column of scalding leaves and soon reached a dirt path sheltered by a blazing yellow canopy. Clouds drifted overhead, blotting out the sky, but they were more an illusion seen intermittently through the amber cover above the path.

Suddenly, a bridge emerged into view making us laugh. Could it be that the thought of trolls hiding in the shadows wasn’t a mere fantasy?  Nemo tried to prove that it wasn’t, dancing toward the water in an attempt to avoid the elevated walkway across the brook. If we hadn’t known him so well, we may have been fooled, but who could expect a self-respecting Golden Retriever to use a bridge when he could wade, or better yet, swim to the other side?

young woman and golden retriever stand on bridge on the way to dover stone church
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Beyond the bridge, a right turn took us directly upriver, along a stone ledge that followed the cliff toward Dover Stone Church. We balanced carefully in spots, but it was mostly wide with sure footing making it easy to tread our way.

young woman and golden retriever navigate the narrow ledge on the way to dover stone church
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In spring, the water runs fast down the Stone Church Brook, but in the fading fall, it flowed a steady stream, rushing faster only where it dropped in elevation. We were actually moving upward, however, going against the current toward the gothic mouth of Dover Stone Church.

The Dragon’s Lair and Beyond

We met the yawning arch of Dover Stone Church in record time. The sound of rushing water faded as we entered the cathedral. Weak light trickled into our path from the cavern opening far above our heads. What constituted a waterfall in wetter months was no more than a trickle dropping into the pool around our feet.

Stone Church is aptly named for more than the arch that welcomes visitors. Once inside, the cool cavern walls invite introspection and a soothing presence descends, accompanying the soft music of the stream.

Standing inside, you feel secluded from the world, making it hard to imagine an early 20th century day, when the banks of the river and the interior sanctum of Dover Stone Church would have been filled with reveling merry makers, enjoying a cooling retreat from the heat of the city. In the waning autumn, with just two women and a dog, the sensitive quiet was palpable, enhanced by the dull light of a cloudy day.

We left Dover Stone Church as we found it, hoping those who followed our footsteps would treat it with similar respect and wonder. Making our way back down the stone ledge along the river we made the decision to venture farther into the Dover Stone Church Preserve.

young woman and golden retriever inside Dover stone church
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Beyond the Inner Sanctum

In 2015, several trails were opened adjacent to Dover Stone Church. We picked up the blue trail after descending the ledges and immediately began heading upward.

This trail was steep in parts and demanding of leg muscles as the general trend was always leading skyward. We were out of breath in portions and did take one short break to rest our legs, but overall found this trail easy to navigate and travel. Footing was mostly firm despite the coverage of fall leaves and was well marked.

We were led a bit astray by some writeups promising a view. It’s there, but you’ll need to peek through trees to see it. The other trails leading across the property are wooded loops that begin and end in the Dover Stone Church Preserve. No doubt, it’s a beautiful way to experience the woodlands in fall, but since they didn’t offer much variety from what we’d seen in the blue trail, we continued onward back toward the car.

Overall, we spent about an hour and a half at the Dover Stone Church Preserve. The trail to the cavern itself is less than a half mile round trip, and the blue loop adds about another mile and a half.

Beyond Dover Stone Church – the Path Toward Abandoned New York State

The town of Dover Plains may be small, but what it lacks in size it makes up for in nearby curiosities, particularly those of the abandoned variety.  One of these sits looming over the valley from atop a hill near the Tenmile train station.

The Wassaic State School for Mental Defectives (later, the Wassaic Developmental Center) opened in 1930. During its peak treatment years, it housed nearly 5,000 patients and staff, offering resort-like accommodations for those seeking help with mental afflictions or developmental disabilities. If you doubt that assessment, you have only to view the directional markers leading you to the cinema, pool and gymnasium.

They’re all closed now. Only a few of the 51 buildings remain open, offering office space for what’s left in the area of the New York State Office for People with Developmental Disabilities. These few inhabited spaces mingle with dilapidated houses and shuttered remaines, a reminder of our journey to understand the complexities of mental health.

Abandoned building at Wasaic State School in Dover Plains, New York
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Other Abandoned Finds in Upstate New York

The area surrounding Dover Plains is quite littered with abandoned history. Driving west along Route 384, we were surprised to find the remains of the Bennet School for Girls. This turn-of-the-century hotel turned women’s college once offered high school and secondary education to well-heeled young ladies from prominent families.

As female education gained acceptance and more young women began seeking post-secondary academics, the school evolved into a junior college, before the trend toward more popular co-ed establishments forced Bennet College into obscurity. A fence now surrounds the old hotel portion of the campus, protecting would-be trespassers from potentially serious harm. Despite attempts to save the building for its historical significance, rumor has it that the once glorious hotel will soon be demolished while the other buildings are sold off to developers.

Exterior shot of the soon to be demolished Bennet School for Girls in New York
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Exterior of the former Bennet College and hotel

Getting lost on a dirt road, we found our last abandoned curiosity. What was left of a large empty house hugged the dirt shoulder, vacant curtained windows waiting sadly for someone to reclaim its forgotten past.

Exploring this area of New York could take days. All around Dover Stone Church are historic markers linked together by scenic driving tours where the abandoned meets the well-groomed properties of the wealthier set.

For us the day was rapidly speeding toward evening, and we had one more stop to make before the afternoon ended.

Dog-Friendly Apple Picking Near Dover Stone Church Preserve

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No New England fall would be complete without our annual apple-picking adventure. Since Halloween was only days away and we had yet to make our yearly pilgrimage to our local orchard, we decided to see what this side of the New England border had to offer.

Barton Orchards in nearby Poughquag caught our attention as a dog friendly establishment. To be certain that internet rumors were true, we headed first to the country store and verified that Nemo was welcome. We also picked up some unique jellies (moonshine jam anyone?) as well as our apple picking bag before heading into Barton Orchards with Nemo in tow (Ok, let’s be honest. We were the ones in tow).

The Barton Orchard property is a vast playground that includes a petting zoo, brewery, corn maze and more than a few types of apples. We arrived late in the New York apple-picking season but still had an ample selection of Empires and Honeycrisps.

When the picking was done, Nemo took his turn as the lone weekday canine in the dog park, showing off his agility skills before we called it a day and loaded up the car with our bounty. It included a large bag of apples, a half dozen freshly baked apple cider donuts and three unique varieties of jellies.

In leaving Dover Plains and the area surrounding Dover Stone Church, we left a lot on our to-do list unchecked. Driving back into the drizzle of the Connecticut western hills, we decided that was ok as it gave us an excuse to visit again and explore the area’s oft forgotten byways.

When Is the Best Time to Take a Dover Stone Church Hike?

If you’re looking for solitude and the opportunity to enjoy some quiet moments alone inside the cathedral, we recommend that you visit Dover Stone Church on a weekday in the fall or winter. Just be aware when hiking in colder weather, many hikers have reported icy conditions. Several recommend the use of crampons.

Days during the spring or sumer, especially weekends, are likely to invite more fellow hikers.

Dover Stone Church Parking

If you’re using a GPS system to navigate to the Dover Stone Church Preserve, it’s easy to be misled. According to the Dover Stone Church Visitor Guide, there is no address for the trailhead and no onsite parking.

Fortunately, the guide does offer directions for finding both. To identify the trailhead, look for a sign posted at the bottom of a gravel driveway on Route 22, just south of the traffic light in the Dover Plains hamlet. (south of the intersection of Route 22 and Mill Street in Dover Plains). After finding the starting point for your adventure, you’ll need to find a place to leave your vehicle as there is no parking in the gravel lot at the trailhead.

The guide provides 3 parking options for visiting Dover Stone Church Preserve:

 Dover Elementary School, located at 9 School St., Dover Plains, New York

 Tabor Wing House, located at 3128 Route 22, Dover Plains, New York

 Freshco 22 Deli & Restaurant, located at 3156 Route 22, Dover Plains, New York

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Dover Plains, NY

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30 minutes to 2 hours

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Bash Bish Falls

Barton Orchard

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Mother daughter travel bloggers exploring the U.S.

We're Kat and Ali, a pair of mother-daughter travel bloggers exploring the U.S. We're sharing our experiences, tips and insights to help you more easily get out and explore the beautiful landscapes and places of this nation.


Kathleen Hesketh

Kathleen is a travel agent with Mickey World Travel, a platinum level Authorized Disney vacation planner, where she helps people discover the magic of a Disney vacation and other travel destinations. She is also the chief author and editor for Seconds to Go - a travel blog where she shares experiences from traveling the U.S. with her daughters. Kathleen has been a professional writer for more than a decade, helping businesses craft compelling content to advance organizational goals.