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…