Haunted Road Trip – Destination: Finger Lakes Region, Part 2 (Tioga & Yates Counties)


Owego Riverwalk


When I left you last time, we had just parted ways with Owego Parkview Restaurant’s owner, Beth Johnson, who suggested we see the Owego Riverwalk and explore Evergreen Cemetery, just up the road. (If you missed that first post, catch up here.)

So, we took a nice walk down the main drag of Owego—tons of cute shops and little cafes! Then made our way back to our car via the Owego Riverwalk along the Susquehanna River. It was a beautiful view, with great landscaping, and perfect weather! We stopped for some caffeine at the Dunkin Donuts next to the Parkview and then headed to the cemetery, just a short drive through town.


Me on the Owego Riverwalk, Owego, NY

Me on the Owego Riverwalk, Owego, NY

Maureen at the Owego Riverwalk, Owego, NY

Maureen at the Owego Riverwalk, Owego, NY









Although the cemetery is not on the trail, we couldn’t pass up a spooky spot that was so close! Evergreen Cemetery is set up in an odd fashion—it’s a tiered landscape, so you really wind up a hill as you drive through it. We passed several interesting mausoleums (one of which we really wanted to check out closer, but decided against it), a Civil War veteran section, and some extremely old graves. Way at the very top, we found the grave of SaSaNa Loft, an Indian maiden who lost her life in a tragic train accident after leaving Owego. From her monument is a spectacular view of all of Owego. Very peaceful.

SaSaNa Loft memorial in Evergreen Cemetery, Owego, NY.

SaSaNa Loft memorial in Evergreen Cemetery, Owego, NY.

After winding back down into town, our next stop was lunch at the Calaboose Grille—the Historic Tioga County Jail turned into a restaurant! This was going to be a fun one.

Calaboose Grille, Owego, NY

As we pulled up to the restaurant, it was obvious the building had been a jail—bars still on the windows, big red brick building. Except for the “Calaboose Grille” sign leading up to the steps, you would’ve thought we were surrendering ourselves! We were greeted by Karlyn Hepworth, who with her husband/chef, Clark, own the Calaboose.

Calaboose Grille, Owego, NY

Calaboose Grille, Owego, NY

The building is now divided into offices, apartments, and the restaurant, although the Calaboose isn’t the first restaurant to be here. The decor (beside the obvious cells) is NOT prison-like. It’s almost a Hard Rock Cafe-feel … very metal with maybe a hint of biker.

As there weren’t any booths/cells available downstairs, we were taken upstairs and sat next to the most haunted cell! George, a drunk who would sometimes imbibe too much just to have a place to stay for the night, apparently liked the jail so much that he’s never left.

Cassie, our waitress, started off by telling us some of the history and hauntings of the Calaboose, including George. She said some workers won’t go into the basement by themselves or close the restaurant alone, and some have quit because of the strange happenings! After placing our order, (more gluten-free options—yay!) Maureen and I played around with the cell and took a bunch of pictures. (Hopefully we’ll never be behind bars ever again.) It was interesting to picture the restaurant as a cell block. But take away the tables and chairs, the paintings hung in the cells, the carpet, and there you have it. It’s an odd feeling to describe, being able to be shut in a jail cell!

George's cell is on the left, ours is on the right.

George’s cell is on the left, ours is on the right.

After we ate, Clark and Karlyn talked to us a little more about the paranormal activity they’ve experienced since opening the restaurant two years ago. They hear cell doors slam and see lights flicker (mainly in George’s cell) and a painting right outside George’s cell was found thrown across the room—it didn’t just drop in place. Karlyn said a mother and daughter were having lunch upstairs and a glass of water on their table just fell over. No one was touching it or near it, no one bumped the table, and the table was sturdy. Staff have felt like they’re being pushed while vacuuming and have heard strange noises at night.

Clark asked if we wanted to go down to the basement—we decided if we’d come this far, we better take full advantage! To get to the basement, you have to go out the back door, through a small parking lot (which used to be the jail yard) and down some SUPER sketchy steps. There was a worker sitting out back and as we looked at the steps going down he said, “Good luck,” with a little chuckle.

How we went into the basement ...

How we went into the basement …

Into the basement we went. To the right, a very finished, nicely painted hallway with a few doors and an old set of giant jail keys. To the left … oh boy. It definitely looked like an old jail basement. Institution gray and green paint on the walls; the eerie feeling was instant. Clark stopped us at a very narrow black and white door. “Solitary confinement,” he told us.

“What?!” I said. “But … it’s so skinny!”

It was the longest, narrowest room I’d ever seen. The door and bars at the top appeared to be wooden. Minimal security? A previous restaurant had used the room as liquor storage. No. Thanks.


Solitary confinement in the basement of the Calaboose Grille, what was once the Tioga County Jail in Owego, NY.

Solitary confinement.

Looking inside solitary confinement in the basement of the Calaboose Grille - what was once the Tioga County Jail in Owego, NY.

Looking inside solitary confinement.













We continued deeper into the basement and came upon the workshop. Clark said it was most likely used as a kind of classroom because of the large chalkboard that was hanging on a wall. I thought the room looked to be in pretty good shape, considering!

After we were back in the daylight, Clark told us that the first execution in Tioga County was actually right in the yard where we were standing. (The Sheriff’s house was attached directly to the jail. A very interesting building from all sides.) Obviously, being a jail, there were other tragedies, but the Hepworths said they like to keep the theme very light-hearted—and I think they’re doing a great job! They have some fun with the names of their burgers and keeping the cells is such a unique touch, but I never felt like I was actually in a jail … unless I really thought about it and freaked myself out. Clark even showed us a picture of George that someone caught on a cell phone!

We thanked Karlyn and Clark for their time and then we were off to Yates County for two of our “Creepy” locations on the trail—the Bishop-Gillette headstone and Spook Hill!

… But not before buying some wine to get through the night ahead of us.

We drove the back roads from Owego up through the Finger Lakes into Penn Yan. We made quick stops at Watkins Glen and Montour Falls, because they were right there! We didn’t realize how close we were to Ithaca, either.

We drove right by Watkins Glen State Park and turned around to stop in for just a second!

We drove right by Watkins Glen State Park and turned around to stop in for just a second!

It started pouring rain as we drew closer to Keuka Lake, but thankfully it slowed to a sprinkle once we reached Lakeview Cemetery, where the infamous Bishop-Gillette headstone is located. Maureen, having attended Keuka College for two years, had visited the cemetery twice, so we were able to find the stone fairly easily! We parked a little ways up the hill and then walked down to the site.

Bishop-Gillette Headstone, Lakeview Cemetery, Penn Yan, NY

The entrance to Lakeview Cemetery in Penn Yan, where the cursed Bishop-Gillette Headstone is.

The entrance to Lakeview Cemetery in Penn Yan, where the cursed Bishop-Gillette Headstone is.

The stone is a massive, simple cube of granite, with just the words “Bishop” and “Gillette” engraved on it—save for the whitish stain on one side. I thought, since it was raining, that it was just a dry spot. Maureen told me that is the image of Matilda Gillette, not a dry spot! I told her I wanted to touch it to make sure. She explained to me that (legend has it) if you touch the gravestone, you’ll wake up with a handprint on your face, like someone slapped you! So, we held hands, and Maureen said, “Hi, Mrs. Gillette. This is Maureen, I’ve come to see you before. I’m here with my friend, Lindsay, who doesn’t believe that you aren’t a dry spot. So for educational purposes, we’re just going to touch it really quick. Please don’t slap us, okay? Thanks!”

I rubbed the stain with my finger and sure enough, it was just the coloring of the granite. The legend of the stone is hard to nail down, like any story passed by word-of-mouth. Several articles say that Mrs. Gillette and her husband made a promise not to remarry if the other passed away, and Mr. Gillette did not keep that promise. So Mrs. Gillette appeared on their shared stone to haunt him and his new wife. The stone was even (reportedly) torn down and replaced, but the image reappeared. The major flaw in the story is that Francis Gillette, Matilda’s husband, died several years before her.

Cursed Bishop-Gillette Headstone at Lakeview Cemetery in Penn Yan, NY.

Either way, it is a spooky stain that definitely looks like the profile of a woman. Do you see it?

From Penn Yan, we took a short drive to Middlesex to try our luck with Spook Hill, where your car rolls backward UP a hill!

Spook Hill, Middlesex, NY

Again, this is very easy to find using the directions from the Haunted History Trail website. You drive up a large hill, all the way to the top, then you stop after a mailbox on the right, but before Spike Road on the left. (There’s a house at the very top of the hill on the left that’s on a MAJOR slant—very weird.)

Spook Hill in Middlesex, NY -- where your car rolls backwards UP a hill!

Spook Hill in Middlesex, NY — where your car rolls backwards UP a hill!

Once we arrived at the top of the hill, we put the car in neutral and … well … you can watch the video for our reactions. We tried it a few more times to make sure it wasn’t our imagination, and then another time on a hill a bit farther up the road, with no luck. What we DIDN’T try (and wish we did; how silly) was to go forward up the hill in neutral. It should work, right? You guys will have to try it out and report back!

Onward to Naples and Ontario County we went, dreading every mile as it got foggier and stormier …

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