Hump Day: Chesapeake Bay Bridge

Despite all the helpful suggestions given the night before at Public House in Denton, MD, I planned to take the most straight-forward route to Annapolis: Maryland Route 404 to US Route 50, which runs all the way to West Sacramento.

However, after sampling a brief stretch of busy 404 on my way to shower at Trevor’s house, I decided against spending hours of getting rattled by tractor trailers. Back roads to the Bay Bridge added four miles, but seemed a lot safer and more scenic.


Dual Span Steel Monster
The Chesapeake Bay Bridge, rising 186 feet and spanning more than four miles, is apparently one of the most terrifying in the nation. It upsets enough drivers that there’s a taxi service that specializes in driving your car over the bridge. Does something like this exist anywhere else?

About eight to 10 bicyclists a month use the taxi because bikes are prohibited on the bridge and for good reason—there’s no shoulder. Here’s my problem with the taxi: I’m not riding an ordinary bicycle. Before I left NYC I called Kent Island Express and found out they had a van to accommodate Countri Bike.

That morning I called to give them a head’s up that I’d need the van in a few hours to make the crossing.

“How quickly can you get here?” said the dispatcher. “The van is going to the shop at 1 PM.”

My legs seized up. It’s 10:30 AM and I’m sitting on the curb outside Trevor’s apartment digging into snacks his wife prepared for me for the road. There’s no way I can make it there that quickly. I explain the situation to the dispatcher and stress just how beastly this bike is. I can’t sustain more than 9 miles per hour.

“OK, what if I pick you up at the Queenstown Premium Outlets?”

That shaves off enough mileage to might actually work. Google Maps calculates my arrival at 12:49. I have no choice but to hustle.

Bringing my beast to the bridge
The back roads are beautiful and mind-calming. The landscape looks like my day plodding across Delaware. I pass through Ridgely, MD and pause to look at the caboose parked on the old tracks of the Delaware & Chesapeake Railroad. Completed in 1867, the railroad through Ridgely peaked with four passenger and four freight trains. The automobile made it obsolete in the 1920s. The line ended passenger service in 1949 and freight service in 1976. At this particular moment, I was the only thing moving through town.

The sun was bright and the sky was blue, but time was ticking. Such pressure far exceeded the restrictive 45-minute Citi Bike rental limit back home. If I didn’t arrive at the outlets by 1 PM I was going to have to hitch a ride or sleep in the parking lot, which I’m sure mall security would not find amusing.

Just Do It
I stayed on back roads for as long as I could, eventually turning onto fast-moving Route 50 for the final two miles. This was the second most nerve-wracking road of the trip (Route 30 through West Atlantic City was still worse).


I triumphantly pulled up to the Nike Factory Outlet at 12:51. I did it! A shopper asked me where the local Citi Bike was around here. I laughed and told her about my ride and we exchanged Instagram handles.

A guy then came out of the store in disbelief: “All the way from Manhattan? Man, that’s a long ride,” he chuckled while retreating to the safety of his automobile.

The taxi arrived 15 minutes late, and the van I had envisioned was nothing more than a normal minivan. We folded the seats down, but Countri Bike barely fit. I awkwardly sat on top of a folded seat with my arms draped over the bike like I was medevacing a wounded soldier.

The ride over the fearsome bridge was painless, and $35 later I was disgorged into the parking lot of the Maryland Natural Resources Police. Who? Another hour of riding and I reached a condo development in Annapolis, the home of my next host.