Maryland’s four-mile-long, 186-foot-high Chesapeake Bay Bridge is nightmare fuel if you’re even a tiny bit squeamish about crossing bridges over open water. At one time, the Maryland Transportation Authority provided free rides across the span. That ended in 2007, and private companies took over—including Kent Island Express, which Steven Eskew has run since 2013. For $45 cash ($55 with a credit card), he or a member of his team will hop into your driver’s seat at a gas station near the bridge, give you a lift, and drop you off on the other side. Here, Eskew talks about what it’s like to help motorists across this daunting structure and what he’s observed about fear.
“I grew up on a little island called Turkey Point. It’s right on the water, and I used to fish underneath the Bay Bridge. [What I do now] sounds like just getting in somebody’s car, driving back and forth, but when you have four cars show up at once or there’s an accident on the bridge or something falls off a truck—you’re dealing with anxiety.
“After Covid, people’s anxiety increased twentyfold. That’s when our business really amped up. During the winter, unless it’s super nasty, we’re doing at least 10 to 12 cars a day. The end of March, because people get spring fever, 12 to 15. In summer, we’ve hit 45. We have regulars. They come every week. A construction worker—six-foot-four, 300 pounds—used the service for 14 years. We have two attorneys, five psychologists. The newest one [is a pilot] for the State Department. It’s men, women, young, old, Black, white. People also take their animals. Dogs, cats, birds, snakes. We had a goat in the car one time.
“The majority of customers sit in the passenger seat and enjoy the view—they just don’t like driving the bridge. A lot of them say they feel they’re more of a danger to somebody else than themselves. Then you get the ones that can’t look out. When I took over the business, I had a lady freak out on me. There was a huge truck, and we were following it. Then some jackass came flying past and went in between the oversized load and the wall. The lady screamed and dug her nails into my arm. She drew blood.
“The other [story] that’s fascinating to me was this lady from New York or New Jersey—I remember the accent. I’m watching her out of the corner of my eye, and she’s turning around in her seat, her face toward the headrest. All of a sudden, she pulls this blanket up over top of her and completely becomes a cocoon. I’m patting her on her shoulder, like, ‘You’re gonna be fine.’ She was just kind of moaning. We pull up on the side of the exit ramp [so she can] drive away. She starts walking back toward the bridge, cussing the bridge out: ‘F— you! I hate you!’ ”
This article appears in the August 2026 issue of Washingtonian.
