I was in Portland all of 10 minutes when its soul rolled by on two wheels: a gentleman pedaling through downtown on one of those ridiculously tall bicycles with an oversize front wheel and tiny back wheel.
The bike, called a penny-farthing, made the man look as if he had just ridden off the back of a deck of playing cards. Or straight out of the 1870s. He seemed barely to notice he was more than a century out of his time.
But then, Portland is out of its time too. Maine’s largest city (not saying much in a state of 1.3 million) is long on modern comfort, but its most endearing feature is a cozy, Old World charm. The town seems almost entirely made of handsome, weathered brick that turns rosy warm at sunset, all the way down to the sidewalks that slope down to a still-working waterfront where gulls squawk and circle overhead.
It’s not so difficult to have that old charm when your town’s engine is what it was when founded in 1786: the docks. Portland’s long, salty docks still teem with stacks of lobster traps, the hulking ships that catch the nation’s seafood, and businesses boasting, “Fishing Maine waters for over 100 years.” They’re open and free for your perusal and offer classic no-frills dining spots such as J’s Oyster, which serves fish straight out of the ocean and appears to have been redecorated approximately never during its 36-year existence.
Head a block from the docks into downtown, and you see still more evidence of a town admiring its past while striving for the future, like the antique “E. Klaman Bottles” sign revealing what one brick storefront was — seriously, there’s a lot of brick — before it became a Life is Good store.
Yet Portland is decidedly modern, packed with more rewards than you’d expect from a town of 66,000. It is eclectic, creative, edgy and alive.
The evidence is in the vibrant arts district of galleries, theaters and a sign promising “Ca$h for your Warhol.” It’s spread across Exchange Street, where you’ll find gourmet ice cream (Mexican chocolate, sea-salt caramel), gourmet popcorn (Maine maple, dill pickle) and a “sexuality boutique” that is “women owned and operated since 2004.”
About five miles outside of downtown, there’s world-class beer from Allagash Brewing. Even the buskers impress; on an unseasonably warm Wednesday afternoon a classical violinist in a long skirt and sandals played a block up from a tattooed guy in a pork pie hat blowing some jazz saxophone.
Then there was the guy driving through downtown in a pickup truck, purple bandanna wrapped around his head, singing along to the Grateful Dead that spilled from his speakers.
It’s also gentle, slow moving enough that if you let your mind drift, you could just as well be in Michigan or Oregon, at least until someone says “toddah sauce,” and then you’re jerked back to the realization that, yes, you’re in New England.
The eclecticism — as well as the rolling streets ending at a waterfront — often leads people to call this San Francisco of the East. It’s a reasonable comparison, albeit on a smaller, calmer, colder level.
“It’s a more innocent version of San Francisco,” said Michelle Gerster, 33, a Bay Area resident spending four months at Portland’s Salt Institute for Documentary Studies.
In true Portland style, Gerster and a classmate were stopping strangers on the street, asking for permission to take their portraits. In the middle of downtown Portland, it made perfect sense.
“Look at that family holding hands,” Gerster said, pointing across the street to a human chain of four breezing down the sidewalk. “That is so Maine!”
“It is so Maine,” said her classmate, Ellen Sherwood, 24, an Augusta, Maine, native who has lived in Portland for about two years.
She said she prefers Portland to her hometown.
“You can do anything here,” she said. “You can go to school and get a job but still have things to do at night.”
But Portland, thankfully, also has some grit beneath its nails that keeps it from being too utopian. There are plenty of hippie types, tattoos (lots and lots of tattoos), and I was asked several times for spare change, albeit with the utmost civility and East Coast brotherhood.
“Spare any change?” one guy asked at the docks.
“Sorry, I can’t,” I said.
“Oh, don’t worry about it!”
He said it so cheerfully that I didn’t worry about it.
Being so small, much of the action — the shops, the James Beard-award-winning restaurants, the bars serving Maine craft beer — are downtown, just beyond the waterfront. Portland is small enough to soak up in about three days, though the east and west end neighborhoods bookending downtown also are worth exploring for their coffee shops and restaurants thick with locals who seem quite glad to be living in Portland.
Unfortunately, at the end of my trip, I never got to do the thing I most wanted to: find that man and his bicycle again.