Stephen Van Lill Jr. may have earned the very first parking ticket in Annapolis.

Near the bottom of its May 1920 front page, the local newspaper reported that Officer William Framton arrested Van Lill for violating the 7-11 p.m. parking ban on Main Street.

“The accused was given a hearing before Justice Welch and paid a fine of $5 and costs, amounting to $6.75,” the unnamed journalist wrote.

That’s about $113 today.

Advertise with us

Annapolis is still trying to figure out its parking problems, 106 years later.

“This is not a fast process,” City Manager Yolanda Lewis said. “I think that the parking conversation has probably been on the top of the radar for a lot of people for a long time, which means that we won’t be able to correct it in a very short period of time.”

What an understatement.

A century-plus of arguments, amendments and angst has gotten the city and its residents where they are today, unhappy with the irrefutable fact that a city center designed in the 17th century struggles to cope with automobiles in the 21st.

This latest round of complaints and promises that solutions exist — like the prospect of a sugar-dusted, free space exactly where you need it — revolves around complicated recent developments.

Advertise with us

Under former Mayor Gavin Buckley, Annapolis mortgaged a big chunk of its downtown parking revenue to invest $100 million in making City Dock better able to withstand rising tides and serve as a public square.

The unintended consequence was two separate companies managing public parking spaces in garages and on downtown streets, apps for different spaces or sometimes a choice and inconsistent enforcement charitably described as scattershot.

The companies say they’re working with the city on problems with app navigation, credit card processing failures and difficulty managing accounts. That doesn’t make finding a spot on a busy weekend easier, and the recent city rate increases annoyed everyone.

Markus Moore, Annapolis transportation director, explains some of the proposals recommended by a parking solutions study group to a Sept. 29, 2026 Annapolis Parking Alliance meeting.
Markus Moore, Annapolis transportation director, explains some of the proposals recommended by a parking solutions study group at an Annapolis Parking Alliance meeting. (Rick Hutzell/The Banner)

Parking also is about politics as much as it is about where to put your BMW.

“We need to have consequences for people that raise our rates, for people that don’t respond to our concerns,” said Katie McDermott, who ran twice for local office in the last year. “We need a boss. We need to have ethical consequences for failed promises, and I hope every politician is hearing that.”

Advertise with us

There is a lot of parking in Annapolis — 1.2 million paid sessions each year. That’s just in the city-owned spaces.

Hewing to city tradition, cue the complaints.

“We are currently at a little over 3,000 signatures on the parking reform petition,” said downtown restaurateur Jennifer Sowers, a founder of the Annapolis Parking Alliance.

Mayor Jared Littmann, Buckley’s successor, heard them. He ran on the notion of perfecting city government — well, making it better if not perfect.

Cue the study commission, another great Annapolis tradition.

Advertise with us

Lewis presented the parking reform work group’s results two weeks ago at a City Council transportation committee meeting. She suggested obvious fixes, divided into phases.

Chief among the first may be updating the tech at the beautiful Mills Hillman Garage — the view from the roof is lovely — so drivers pay when they go out. Moving to a single parking app and one contractor would be good, too.

The number of spaces open at the Mills Hillman Garage in Annapolis helps motorists find a place to park. Adding more signs around the city has long been a suggestion to improve parking.
The number of spaces open at the Mills Hillman Garage in Annapolis helps motorists find a place to park. Adding more signs around the city has long been a suggestion to improve parking. (Rick Hutzell/The Banner)

“We were really focused on how to make parking feel like it was a good customer experience,” said Lewis, just four months into her job. “So most of the recommendations will pivot from that point. We knew people felt that there were arbitrary actions, maybe even predatory actions, for trying to park.”

I have to pause here and confess I have an unpaid parking ticket.

I was doing an interview downtown, parked in the Mills Hillman Garage and overstayed the time I paid for in advance.

Advertise with us

I can’t figure out how to pay it. Turns out there’s a moratorium on violations until progress is made on that whole notion of enforcement. At least that’s what I’m claiming, anyway.

The work group doesn’t address other long-standing problems, including employees of downtown businesses who must find their own parking. Employers don’t seem eager to help pay.

The mayor’s committee will hold a town hall Thursday to hear public comment on its recommendations. It’s virtual, so there’s no need to park downtown.

Members discussed some of them Tuesday in the First Presbyterian Church basement. A few, such as better enforcement, seemed good.

“Regardless of what changes might come in the future, and what might come out of this, enforcement is very erratic,” downtown resident Amanda Fegley said.

Advertise with us

Others sounded like magical thinking.

“We need to add 800 spaces downtown in the next 10 years, or — catastrophic disaster,” said Andrew Fox, owner of several downtown restaurants. “When I say downtown, I mean downtown.”

Long-term ideas in the city report, like “way-finding” apps and signs that would point to available parking or adjustable pricing to push drivers into garages rather than onto residential streets, aren’t new but still sound good.

Maybe the city can even combine state and county garage management.

“We’re not there yet,” Lewis said. “Suffice to say, the conversations have started.”

Advertise with us

Whatever happens, it’s far too late for poor Stephen Van Lill Jr. He died in 1962, perhaps never realizing his pioneering place in Annapolis history.

The city didn’t even create its own parking law until Dec. 1, 1922, relying instead on piecemeal rules.

The debate on that first parking code started in 1919, when residents noticed the number of cars on city streets swelling. It lasted three years.

The view from the top of the Mills Hillman garage in Annapolis can be lovely on a Tuesday night, and a little lonely.
The view from the top of the Mills Hillman Garage in Annapolis can be lovely on a Tuesday night. You can almost see the future. (Rick Hutzell/The Banner)

“The city council has been forced to take stringent action looking to relieving the situation at least on some of the thoroughfares,” the staff of the Evening Capital wrote.

Even the word “parking” changed, evolving from a noun describing a strip of roadside grass and trees to a verb for driving into designated spaces and a noun for the spaces themselves.

And something even bigger — defining life in an old city on the Chesapeake Bay.