Ohio Jail Tour: Doing Time with Steve Caballero

Get Busy Riding Or Get Busy Dying

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

The last place you want to go is jail. This is the story of how I took my teenage hero and boss to jail, twice! My hero is skateboard legend Steve Caballero. My boss is paycheck legend Jordan Mastagni. The three of us are on a road trip across Ohio hitting skateparks and going to jail. Work with me here. I figure if we’re trying to go to jail it will be like the whole musician “break a leg” good luck thing. Reverse psychology. Know what I mean? Okay, you don’t care. Let’s play a little game of fill in the blank.

“Come and enjoy your stay at The Old Vermilion _______ B&B. Relax in comfort and indulge your dreams in the perfect getaway. Located in the heart of Vermilion’s Historic Harbor Town District, our _______ is perfect for a romantic evening, family vacation, girls or guys night out, and we can even provide the backdrop for your proposal to the love of your life.” Wow this place sounds pretty sweet, right? Somewhere you could really unwind and spend some quality “me” time. The website I’m reading from goes on to say, “The Old Vermilion _______ is within walking distance of all of the attractions that Vermilion has to offer, including shopping, fine dining, beaches, the harbor, and more.”

By now you’re thinking, okay, this is easy. _______ is a resort or spa hotel. The kind of place a desperate man takes his woman to when he’s swinging for the fences. When he’s either really sorry or he really wants to get laid. _______ is a place where he can show up with confidence knowing he made the right choice. Right…

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

The website is from Ohio's Old Vermillion Jailhouse B&B (jailbed.com). That's right, jailhouse. Only in America is there an industry committed to providing its customers the most pleasant and comfortable stay in the place you spend your entire life avoiding. It's an interesting stop on the food chain if you think about it—a national network of businesses surviving on people's fascination with going to the clink. It's a safe peek into the abyss of human suffering and mental torture, a fun place to spend the afternoon with the family congratulating you on your life choices.

I learned about the Old Vermillion Jailhouse thanks to Debra at the Old Jail Inn Parke County (oldjailinn.com) in Indiana. I did a story on her wonderful penal institution in a previous story for Baggers a few years back. If you're a glass half full kind of person, the influx of national prison construction has created a lot of new opportunities for outdated prisons to be transformed to museums and bed and breakfasts.

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

The Old Vermilion Jailhouse B&B is a private inn that can accommodate up to four guests who get private use of the 600-square-foot facilities. Originally built as the town library in 1935, the building was later transformed into a jail in 1958. The jailhouse took on its current incarnation in 2013 and now offers a room with one queen bed, which the shortest guy of our group, Caballero, took. The other two rooms are tiny jail cells each with a single bed. Note: Jordan and I are both over 6 feet. Thanks, Cab. Actually, the smaller beds are pretty comfy.

Nightly and weekly rates are available and include free breakfast. When I asked Steve how he enjoyed spending the night in prison by choice, he had this to say: “What was awesome was how they persevered the old jail and made it into a hotel that felt inviting and comfortable for what it was once used for. What a great idea and business opportunity. That place was fun.”

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

Now let’s just be honest here: We’re talking about a jail. No matter how comfy you try and make it the place was designed to confine the soul and mind, not comfort them. The big draw for this place these days is the owners Markos and his wife. They’re gracious, welcoming people who planned on having the mayor of town there to meet us, but sadly we arrived too late. Markos also wanted to put a press release in the paper, but we humbly declined in fear of the entire town disturbing our beauty sleep. Steve, Jordan, and I just wanted to eat and get to bed after a long day on the road. The bulk of our day was spent traveling part of the 293-mile Lake Erie Coastal Scenic Byway from Sandusky to Vermillion.

Steve has an enormous Instagram following (@stevecaballero) that he spends hours on responding to comments and messages. I think this deep dedication is part of a cosmic ripple effect that touches people like Dan Smith, director of creative marketing at our next stop, the Ohio State Reformatory (ohiostatereformatory.org).

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

Dan wrote me a nice letter prior to our visit explaining the tour process and options. Between the info about self-guided tours and what the prison has to offer, Dan spoke of his time skating and what it meant to him: “That’s great about Steve Caballero coming! I would love to get a picture with him and meet him. I loved riding my skateboard back in the day. Skating will always be such an important part of my life.” Many years later and Dan is still stoked on meeting the one and only Cab. Dan had graciously offered to let us in for a tour before they opened to accommodate our tight schedule. Sadly we couldn’t accommodate our own schedule and kept Dan waiting an extra four hours (sorry, Dan). I told you Steve spends a lot of time on Instagram. Good for his fan base but bad for our schedule. In our defense, there are a couple highly distracting roads surrounding the Reformatory.

The first road of many distractions runs right past the Reformatory. The second generation of the Old Lincoln Highway on route 545. The route has gone through three generations of changes, improvements, and realignments. It’s said to be one of the earliest transcendental highways in America and predates the famous Route 66.

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

The other route nearby is the Shawshank Trail (shawshanktrail.com). Located between Upper Sandusky stretching East to Mansfield along Highway 30, the trail stops at 14 sites used in the filming of The Shawshank Redemption. The trail was created by the Mansfield/Richland County Convention & Visitors Bureau in 2008. One nice feature of the trail is there is no official start or end point; visitors can follow their interests on their own schedule.

The Ohio State Reformatory is a humbling place to visit. Best known as the location for the motion picture The Shawshank Redemption, the structure is a preserved window in time. It was impossible to not feel like Andy Dufresne touring the grounds. The line “get busy living or get busy dying” is a quote from the movie that crosses all racial and social boundaries. It perfectly sums up the movie and is a great road map for anyone trying to live a full life. Steve was also touched by the movie and had this to say: “The movie is one of my favorites, and it was really neat to be in the rooms they filmed the actual movie in. It brought back cool memories about the flick. Can’t believe they almost tore the place down. For a small town it’s definitely worth the visit because of how great the movie was. It’s a true classic indeed. The personal tour we got was simply amazing, and I’m stoked they took the time to give us the history lesson of the place as well. I learned a lot about the prison.”

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

The Reformatory is old, it’s bleak, and it’s badass. I know that sounds weird saying a prison is badass but it is. To me, anyway. Don’t judge me! Witnessing the shitty living conditions and homemade weapons in person without the threat of a violent rape almost makes the horrible reality seem cool the same way NWA made living in Compton and being in a gang seem cool. Probably feels cool too because I can walk out of this jail at my leisure.

The OSR requires no disco balls to draw your attention. It relies simply on the prison’s long, fascinating history. The memorabilia and facts detailing the filming of the movie are fascinating and connect you to the reality of life behind the walls in a personal way.

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

Designed by Cleveland architect Levi Schofield, the prison was built between 1886 and 1910. At the prison's peak activity in 1955 it housed 5,235 prisoners. The prison was eventually closed by court order in 1990 due to overcrowding and inhumane conditions. The state sold the facility to the city of Columbus in 1995 and has been open to the public ever since. The East Cell Block remains the largest free-standing steel cell block in the world at six tiers high. Visitors of all ages from around the world come annually to soak up the building's history, from its stunning architecture, to its history of reform and rehabilitation, to the major motion picture The Shawshank Redemption being filmed on location in 1993. Open daily from April through September the prison hosts music events, a tattoo convention in July, a Civil War re-enactment in August, and a Halloween bash in October.

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

Our tour of the facility was an attention grabber. We had planned on spending an hour and we ended up staying for three. Steve, Jordan, and I were shown around by a former inmate named Michael Humfrey. Michael was an inmate from 1969 to 1970. He served 14 months on auto theft and grand larceny. He didn’t commit the crime but was roommates with the culprit. When Michael refused to give up his friend he was incarcerated. Michael was paroled in 1970 and later pardoned in 2004. He is now the lead tour guide at the facility. His knowledge of the grounds and his personal story were incredible. He showed us the actual cell he lived in and shared his story of how he ended up a guest of the state. It was deeply moving that after that nightmare the guy still wants to be a part of sharing his experience in the building that took so many years from his life. Steve, Jordan, and I all left the tour with a new appreciation for life and freedom.

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

As the three of us were leaving, Dan generously offered for us to spend the night at the prison. I was crushed that our schedule didn’t allow us time. This place is the real deal—no B&B comforts, just tiny, uncomfortable cells—and rumors of ghosts sounded like a dream to me, no pun intended, but sadly we needed to be on our way.

During our time in Ohio soaking in all the history of crime and punishment I kept coming back to the phrase “skateboarding is not a crime.” It’s a battle cry for disgruntled skaters across the country who are constantly being harassed and kicked out of skate spots by the police. The funny thing to me about that statement is, yes, it actually is a crime if a city has it on the books. Regardless of who is right or wrong, the tension is a daily reality for people who choose to ride a skateboard instead of a bicycle. Use a skateboard, go to jail.

motorcycle touring and skateboarding
Ohio Jail Tour: Doing Time with Steve CaballeroMike Calabro

Here we were in our second jail in two days and before hitting the road we had one thing left to do. Get busy skating or get busy dying. We’re traveling with a skateboarding legend. If anyone can get away with skating in a jail it’s Cab. “I believe I’m the very first person to ever ride a skateboard in the prison, let alone ollie down the prison cell hallway,” Steve said.

What he couldn’t get away with was going unnoticed by his fans. Even in remote Ohio in a prison there are people who know Cab and want his autograph. The irony of watching a famous skater being stopped for autographs while skating in a maximum-security prison was more than my little brain could handle. I was giddy with joy. I was skating with my teenage hero, getting paid to ride motorcycles, and I got to walk out of two jails in two days when I felt like it. Not a bad deal.