Herrmann’s Castle & Greenport, NY

Jonathan A. Neary
11 min readDec 21, 2020

“I’m glad to be so young, talkin’ with my tongue, glad to be so careless in my way, glad to take a chance, and play against the odds, glad to be so crazy in my day…” Steve Forbert sang, as I grinned and wholeheartedly agreed from the driver’s seat. Conflicted but still high from the renewed sense of living I possessed — after the agonizing recovery from my surgery — and two years since Carol had joined us on our jaunts across Shelter Island, I felt blessed to be back again. Not only was I alive, my health was finally improving. The next couple of weeks were marked by short trips to local events, including the Greenport Maritime Festival, and the joy of company who doesn’t wear a Nurse’s badge.

In Carol’s honor I played a lot of Van Morrison, whose napped velvet vocals reminded me of the days we spent jamming out to “These Dreams of You” at a plethora of boat launches when we were killing time between adventures. It was hard to keep her from my mind as we retraced several of the same miles she had been present for. Despite my medical victory and subsequent outlook, sometimes I felt like a pencil that’d been dropped on a concrete floor — sharp and complete on the outside, but liable to break frequently from the fractures in the lead beneath.

Folks from “Out East” refer to Connecticut as a “hop, skip, and a jump” away, due to the two little ferries on either side of Shelter Island, and the big ferry from Orient Point to New London. Greenport was consequentially a hop and skip away, unless the driver was willing to “drive around,” heading West to Riverhead before doubling back. On a larger scale, “driving around” also meant driving to New York City before doubling back to central Connecticut, instead of riding the big boat from Orient.

During these treks I chose to take the little ferries, absorbing the beauty of Gardiners Bay along the way. “Oh, the water, oh, the water, let it run all over me, and it stoned me to my soul,” Van-the-man-Morrison affirmed. In the past, Carol had opted to be the designated driver on our trips to Greenport, so long as we parked near Dering Point and bought “walk-on” tickets for the North Ferry. Significantly cheaper, we continued this tradition; Whitey and I boarded and prepared for the Maritime Festival, which hosts thousands of visitors each year, showcasing tall-ships, kayak races, local food, drinks, and gifts, and demonstrations of woodworking and model ship building.

After catching the tail-end of the parade, snapping a couple photos of the fire trucks, we moved and mingled with the crowds to explore the local vendors; I snagged a sweatshirt sporting a big anchor on the front, and “NOFO” on the back, which was short for the “North Fork.” Greenport Brewery was heavily represented, which suited me just fine as an avid fan of their beer; I chugged a Black Duck Porter before weaving through the sea of bodies in the street. We came to a couple of classic cars, where the closest DJ blasted Morrison’s “Brown Eyed Girl,” launching the surrounding mob into motion. Evidently we had come to the right place! The experience cemented my plans to return a few days later with Heineken Mike, though our pit-stops on Shelter Island quickly became my favorite detour.

Heineken Mike was a mutual friend of John, Whitey, and I; a scatter-brained former tennis pro who drifted into the Hamptons one day, and swindled his way into our family-friend-unit by driving a local restaurateur home one night and evading a deer in the headlights. After being offered a lifetime supply of libations in exchange for safe passage, he expressed his affinity for Heineken, and while his beer preference changed, the name stuck. His acquaintanceship with John followed a night of drinking at the Boathouse Restaurant, when John’s cab driver asked if he minded sharing a ride. With nowhere in particular to go, Heineken wound up getting dropped off at John’s after stopping at the gas station for a twelve-pack.

“You gonna drink that?” Mike asked, motioning to a bottle of Robitussin on the kitchen counter.

“Nah,” John replied, and within a few moments the bottle was empty.

After passing out for the evening, John awoke to a surprisingly clean but empty house, and was worried for a moment that he’d been robbed. Calling a cab to return to the Boathouse for another round, he walked in to a friendly “hey buddy!” from a familiar face; it seemed Heineken was tuned into the same frequency. Later that week in the same cab they’d met, Mike picked up the fare by pawning off a “fauxlex,” or fake Rolex watch, something the driver has not yet forgotten.

On a quiet Tuesday in the heart of September, I drove us out to Crescent Beach on Shelter Island; no fare or knock-off jewelry required. Overshooting the Sunset Beach Hotel, we continued toward the tree line when I noticed a derelict building to our left. Standing four stories tall, with the basement boarded up, it screamed: “turn around,” and that’s exactly what we did — pulling a U-Turn and heading up the hill, we veered off to the side as we acknowledged the landscaping crew working on the property next-door.

Nestled in the wayside was a brick archway with an ornate iron gate, with “Herrmanns Castle” emblazoned on a set of white tiles beneath a concrete bust. Behind it rested a plywood-boarded garage door with 2x4 “locks,” beneath the mural of a dock and sailboat on the coast. “My clicker isn’t working!” I mused, pressing my thumb against an imaginary remote. “Someone let me in!” I shouted, before looking over my shoulder at the landscapers.

“What are you waiting for?” Heineken asked, immediately hopping the fence. I was nervous about the eyes which could potentially land on us, but I followed suit, skirting the outside of the property as we checked out the overgrown tennis courts and the backyard. There was a old computer monitor smashed up in the grass, which reminded me of the years I spent typing scholastic papers and playing Oregon Trail. A handheld roller sat rusting away atop the clay-dust court, begging to be weeded and maintained in time for the afternoon match. As I looked for an access point, Mike simply walked up to the front door and gave a push, exposing the rotten boards designed to keep us out. The door swung open and we slipped inside, giving way to what I would dub the “ultimate party mansion.”

“Look at this!” I exclaimed redundantly, stepping from the foyer into the living room, which had a brick wall surrounding the couch which faced the fireplace. Beside the ingle was a surprisingly tall metal door to access to the damper and make cleaning easier. Overhead, an ensemble of ceiling tiles had collapsed around the fan, and insulation was crumbling onto the ceramic floors.

Around the corner was the entirely-too-small kitchen, though its decor was absolutely gorgeous, and the arched and brick-lined serving window reduced its claustrophobic traits. “Don’t you hate it when no one leaves a drop of soap?” I declared, shaking the empty bottle of Dawn. A couple of small plants were still clinging to life beneath the window; I would gladly have cared for them if the water were not shut off. Regardless, they seemed to be more in tact than the structure itself, which had been patiently resting its fate upon the Zoning Board and multiple architects.

While the original plan included a modernization of the existing structure, by the time the final approval was granted, the plans had changed to include new construction. Thus the building’s days were numbered, and within two months it would be demolished and erased from the shoreline forever. We were a couple of the last feet to walk its floors and see the property through the eyes of Walter and Ingrid Herrmann, the German immigrants who built the home in 1973 to reflect their vision of a Bavarian chalet.

Originally a baker, Walter first landed in America in 1936 when the ship he worked on was quarantined in New York after a typhoid outbreak. After bouncing from Manhattan to Florida, his status as an illegal immigrant led to his deportation, and he found himself in South America during the boutade of World War II. Herrmann was interred in 1941 as a result of Brazil’s Declaration of War and subsequent treatment of all Germans in the region. He wouldn’t return to the United States until six years later when he was granted legal status, during which he began to branch out into contracting and construction. Using his artisanship, Walter built most of the “Castle” himself, paying extraordinary attention to detail.

Ingrid Herrmann passed away in December of 2009,in her early 70s, and Walter passed almost three years later in his 90s, leaving their legacy behind on Shelter Island. The couple had made their mark among locals as generous hosts and excellent cooks for decades. While the cogs of government grind slow, they were responsible for responding to Developer Zach Vella’s requests for work on the property within the same year Walter had passed. Ultimately, the Herrmanns’ Long Island benefaction would be met with a wrecking ball, but on this autumn afternoon Heineken and I experienced it for the first and final time.

Walking up the stairs we admired the woodwork and the stone walls, ascending to a penthouse-like viewing room. Encased in floor-to-ceiling doors and windows, divided only by massive mirrors, the top floor was the opposite of the kitchen down below. Sporting a panoramic scene that included the beach and tennis courts, I could only imagine the parties that were held here. If I ever won the lottery, this room alone would lead to my demise. Evidently the Herrmanns used to utilize the space during fireworks displays, and I fantasized about being one of their honored guests on such an occasion.

As we exited the building, I glanced upon another ceramic work of art: a knight riding a golden horse with lance in hand, affixed to the stucco wall beside the entrance. Cautiously checking all directions, we hastily made our escape. I had certainly pushed my luck with local police in the past, and I was hoping karma wouldn’t cash in the years of chips amassed. With a rumble in our stomachs, Mike and I bee-lined back to the car and headed for the North Ferry; we were about to embark on the “skip” portion of our passage.

Arriving back in Greenport, Heineken Mike and I quickly made our way to Claudio’s: a historic mainstay of Long Island since its conception in 1845. During the prohibition period of the 1930s, bootleggers cut a trap door into the dock for the discrete delivery of spirits, which were transferred to its upstairs bar. Today it draws tourists to the region, who indulge the bar and restaurant, which is still under the ownership of three local families. I ordered a flounder sandwich with hand-cut fries, and washed it down with a Greenport Harbor Ale. Heineken opted for a “liquid lunch,” stretching out on the pylons at the end of the dock. The neighboring yacht posted a “No Boarding” sign, which Mike defied by placing his leg on the deck, smirking as he broke the rules again.

Wandering our way to the North we explored Main Street, which had been packed to the gills just days prior. The iconic carousel was now just as abandoned as Herrmann’s Castle, featuring an endless flow of colorful vacancies. The rows of glass kept us at bay while creating the illusion of a decorative Christmas tree behind us, though the post clocks were still adorned in late summer flora. I knew that seasons were going to change quickly, but I felt as though this little moment in time was going to last forever. After wandering the docks, chatting about nothing-in-particular, and grabbing a six-pack for the road, we headed back to Shelter Island, skimming the bay once more.

Making pit stops at Reel Point for a ceremonial long-neck, and Wades Beach for the sunset, I reenacted the summer of my past. The natural world was in full swing, despite my memories getting frozen in time. Envious of a bumble bee laying claim to some goldenrod, I related to the simplicity of merely moving task to task; as monotonous as it may be, sometimes it feels like the best path in life. We had witnessed a castle suitable for rats and peasants that day, but I was desperate to attain access to the kingdom of God, where I was sure Carol and Delilah awaited. For now I would have to settle for the comfort of mobility: the freedom to explore the world in the company of my choosing, with the bittersweet recognition of a healing heart. Van Morrison offered insight to the season, singing “these are the days of the endless summer; these are the days, the time is now… There is no past, there’s only future; there’s only here, there’s only now.”

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Jonathan A. Neary

The outdoors is where I work and play. Torn between my love of nature and urban exploration, I use photography and writing to bring out the best of both worlds.