At the base of the hill, pull into Congress Plaza and behold the most unsettling arrangement of trash receptacles ever known to man near the entrance to the Rite Aid pharmacy. Take a moment to dry-heave in or around one of the cans before draining the last drops from your driver’s water bottle, commenting on her terrible haircut, and pressing on down Congress Street until you get to Pearl Street. Take a left onto Pearl Street and go to the intersection with Fore Street.
Force your head to turn left. These soulless offices at Custom House Garage used to be a vibrant Italian neighborhood. Gasp, shriek, and wipe your tear-stained face on your pal’s shirt before taking a right on Fore Street and heading through the center of the Old Port, making sure to avoid being crushed, either in body or in spirit, by the Downeast Duck Adventures amphibious tour bus.
At Union Street, take a left and cross Commercial Street, bearing left, to the Dimillo's parking lot. Don’t stay too long, since the mojo here is so bad it might suck any appreciation of aesthetics — good or otherwise — right out of you (though your pal likely has nothing to fear if that repellent outfit they’re wearing is any indication of taste). Back on Commercial Street, take a left.
Demand your driver weave through the despicable snarl of cars and tourists here about 200 yards to the Fisherman's Wharf public parking lot where you must avoid looking up at all costs or risk being blinded by a passing bird’s waste. Wonder why, oh why, Portland’s parking lots gobble up such nice real estate in a walkable city. But don’t wonder too long. Ride away before getting tagged by heading left on Commercial Street and taking a right onto Center Street. Follow Center up two blocks to Spring Street and take a left. By this time, your driver will be gasping for air and looking so wretched you wonder why she even left the house today.
But you’re not done seeing the worst of the pretty city. Behold one of the architectural wonders of ugly Portland, the Cumberland County Civic Center. If Gilbert Gottfried were a building, he would be the Civic Center. Not you, not your driver, not even your pal would do Gilbert Gottfried. Continue biking up Spring Street until you get to High Street; take a right and then a left onto Congress Street.
Keep a lookout for Geno’s club about a half a block down on the right but try not to look at the empty lot just beside it. As your driver quickens to outrun the ugliness of yet another underused lot, you might think you’re home free. Think again. This stretch of Congress Street from Longfellow Square to 7-Eleven is one of the nastiest in town. Go faster, and don’t forget to dodge the ne’er-do-wells and friends of ours who frequent this block. At Bramhall Street, take a left and bear right, staying on Bramhall, until you get to the Western Promenade, from which you can see one of the most beautiful views of the sunset in the city. Whew. You and your pal made it. Even your rickshaw driver now passed out on the grassy promenade made it. You survived Ugly Portland. Or did you?
