A parking sign near the corner of Market and Middle streets in 2022. (Derek Davis/Staff Photographer)

On a recent Friday evening, I did something that, for a lot of longtime Portland residents, would be unthinkable.

Right around dinnertime, I drove straight into the Old Port, headed for Exchange Street, hoping to find a place to park.

I’ve heard a lot of complaining this summer about how difficult it is to park downtown, but I haven’t noticed it’s gotten any worse than it has already been for years. Maybe it’s because I have lower expectations about being able to find a spot quickly or close to my destination. Maybe it’s because I avoid going into town when it’s busiest. Maybe it’s because I aim for the outskirts and side streets first, accepting a longer walk upfront in favor of a shorter search.

Determined to figure out whether the whining is overblown or I’ve just had good luck, I’ve been taking note of how long it takes me to find a spot whenever I’ve parked on the peninsula in the past month or so.

First, there was the Thursday night comedy show at Empire. Granted, I didn’t waste any time heading out the door after the end of my work day at 5 p.m., but I did try to get as close to the venue as possible and drove right up Forest Avenue then took a left on Congress, where the club is located.

Having not seen any spots along the way, I took my first left, onto Oak Street, where a car parked next to Nosh was leaving. Doesn’t get much closer than that, and I even nabbed two spots at the bar at the notoriously busy Empire Chinese Kitchen for dinner before the show upstairs. Winning.

But just after 5 p.m. on a weekday probably isn’t the worst time to try to find parking downtown, since it’s also when a lot of workers are leaving.

I would have thought it even easier on a Monday afternoon, but not so on the week in July that I, and maybe everyone else, was on vacation. I had decided it was time to revisit the happy hour at DiMillo’s that I’d discovered on a bar crawl this winter, and as I drove in from West Commercial Street, I could tell it was a scene down there.

I pulled into the first space I saw, near Browne Trading Co., but it was metered, I was coinless, and there was no Passport Parking zone number in sight. But, aha! I was going to DiMillo’s. I could park in the lot and get my ticket validated, which I normally avoid doing in case I want to go somewhere else in the Old Port afterward, but this seemed like a time to take advantage of the option and worry about that later.

Indeed, after finding out DiMillo’s happy hour specials aren’t offered in the summer, I had a drink and a snack, then decided to move on to the next stop from my tour, Three Dollar Deweys, for its food deals. By then, the crowds had calmed a bit. I managed to take a left out of the lot onto Commercial Street and found a diagonal spot on the other side of Union Street from the pub. Too easy.

I could go into detail about how I got a spot on Hampshire Street, right outside Tomaso’s Canteen on a Sunday afternoon, or put on a clinic on parallel parking under pressure trying to get to newly reopened Dry Dock before it filled up, but you get the point. I have my ways, as I’m sure most city dwellers do.

For our purposes, however, I wanted to find out what would happen if I ignored all my instincts, forgot all the tips and tricks to parking in Portland that I’ve picked up over the years, and just barreled into town at one of the busiest times of the week at the busiest time of year, set on parking in a prime location, to see how long it would take.

On my way to what the Apple Maps app identifies as the center of the Old Port (the intersection of Fore and Exchange streets), I bypassed a couple empty parking spaces on Congress Street near City Hall, a favorite stretch of mine for a good shot at a spot in the evenings.

But I was trying to think like someone who assumes they could get closer and, at 5:46 p.m., turned down Exchange. I didn’t stop when I saw brake lights on parked cars, as I normally might, just long enough to see if there’s any movement. I took a left on Fore Street and another up Market and drove by a free spot designated for 15-minute parking until 6 p.m., which in hindsight would have been fair game.

Seeing the uppermost block of Market Street was full, I turned right on Federal and kept going straight into the courthouse parking lot, a sure bet on nights and weekends in the Portland of yore but hardly worth bothering to try these days, that evening included.

After circling to the exit, I went down Pearl Street, where I often still have luck but not this time. I peeked down Milk Street on my way, formerly a pro move, but apparently the jig is up. I tried my luck turning left on Fore, but the few spaces there were full, so I took a right on Franklin and then another on Commercial, what I assumed would be a fool’s errand.

But as I rolled past Dana Street, a silver Mazda was backing out with no cars between us. By 5:57 p.m., I was parked — about a minute walk from my destination, within 11 minutes from the start of my search, which included waiting for pedestrians at crosswalks and lingering at stop signs to jot down notes.

And that’s doing everything wrong. I don’t think anyone, with the time and ability to walk a bit, is in danger of having no choice but to pay for a United Parking Partners lot anytime soon. But let’s hope the tourists do and leave the good spots for us.