It’s difficult to say exactly when Portland entered its current era — one in which the city routinely makes national top-10 lists, is well known for its restaurants and has a near-zero apartment vacancy rate.

But for many, the city’s current reputation has only deepened their nostalgia for a different time — the one that came after the shipbuilding boom of the ‘40s and ‘50s, but before the recent hotel and condominium gold rush — when Portland was home to a rogues gallery of scoundrels and characters, and you could see pornography in a theater on Congress Street.

Those who lived through it describe it as hardscrabble and rough, a little seedy and dark. But it was also genuine, affordable and close-knit.

This is a story about what a few people remember of that Portland. To borrow a phrase from the Portland Phoenix in 2008, we’ll call it the city’s Red Light District Era.

Take the historic Eastland Park Hotel as an example. It welcomed famed aviator Charles Lindbergh in its early years and had the clout to turn away First Lady Eleanor Roosevelt in the ‘40s. In recent years, the property has followed in the city’s trendy revival, undergoing a $50 million renovation and reopening under the Westin name with more rooms and higher prices.

But during the Red Light District Era?

“If you waited in the alcove of the doorway of the Eastland, people would assume you were a prostitute,” recalled author Suzanne Strempek Shea, who lived in the city in the late 1970s. “If you were just stepping out the rain, waiting for a bus, or waiting for someone to come in, people would say some pretty colorful things to you.”

Next door, where the public open space Congress Square now exists, was a single-story commercial building.

“There was a Dunkin Donuts at the corner of High and Congress where ‘ladies of the night’ would hang. Also on lower Preble Street, near where the soup kitchen is now, there were a couple of ‘all-night clubs’ — BYOB,” said John Duncan, who worked as a cab driver in the city in the 1970s. “I worked nights, so after midnight I would get a lot of business running from Preble Street to Dunkin Donuts and such.”

Then there was the old Stardust Inn, something like a gentlemen’s club on the eastern Congress Street location where the pub The Snug is today. It closed after a fire in the mid-1980s — long before the Internet could take proper inventory of it — but whispers of the place still exist on social media and reader comment threads, where it’s been called “a place of joy for many lonely men.”

“Located in the best part of Portland to get stabbed, mugged, or worse; this place drew me like a moth into a flame,” wrote photographer Jim Boynton on his Flickr page years later.

In a review of two Portland history books in 2008 for the Phoenix, writer Brendan Hughes recalled stories of a colorful local crossdresser named Stanley “who either worked at or was an extremely reliable patron of the Stardust Inn.”

“The Stardust, with Stanley dancing on the billiard table, would have made today’s Old Port Tavern look like a tearoom,” Hughes wrote.

Longtime Portland resident Bonnie Blythe launched the Facebook page “Portland Encyclopedia of the 1960s, 70s & 80s” as a place where people could trade photographs and stories of the city from those decades.

Blythe was able to rattle off the names of a number of rough spots in the Old Port from 30, 40 and 50 years ago — there was Joe and Nino’s Circus Room, Sloppy Joe’s and the old Seaman’s Club, where the friendly pub Bull Feeney’s is today, but where motorcycle gang members notoriously gathered in decades past.

There’s The State Theater on Congress Street, which opened as an ornate first-run movie theater in 1929 and prospered until the 1960s, when it fell onto hard times and became a pornography theater all the way up through the 1980s.

After 20-plus years of stops and starts thereafter, The State has now reclaimed its place as a (clean) center for entertainment in the city, a concert venue attracting some of the country’s most recognizable acts.

The construction of the Maine Mall in neighboring South Portland in 1971 triggered an exodus of retailers from downtown Portland and left an ambience of boarded-up storefronts.

As Duncan recalled, the Red Light District Era had its danger and drugs — there were those two High Street addresses “we all knew of as places to score drugs” — but there was also a camaraderie among Portlanders trying to get by in a tough city with a bad economy.

There weren’t all the five-star restaurants or luxury condominiums, but there were plenty of parties and the rent was a fraction of what it usually is today.

“Then, we were finding apartments for like $100 a month,” author Strempek Shea said. “It was affordable, and I don’t know how affordable it is now. I think you lose your blend of society if only the rich can afford to live there.”

Added Blythe: “Portland was rough, but I think it’s important to balance that with the sweet memories natives have of Soule’s Candy Kitchen, the Village Cafe, shopping at Porteous Mitchell & Braun, the Splendid Restaurant, [and] downtown at Christmas time.”

There were characters now remembered warmly as making the city a more colorful place, like the “Dogman” David Koplow, once described by the New York Times as “a sign painter, college dropout, amateur lawyer and civic gadfly” rarely seen without his small pack of unleashed dogs.

“It really was a totally different place. You wouldn’t even recognize it,” Strempek Shea said.

The author wrote a nostalgic commentary for Down East magazine recently in which she recalled some of her favorite haunts, as well as a peculiar laundromat incident in which she had to shield her eyes from the sight of a recognizable local stumbling in from the street and pulling his clothes off.

Those were the days.

“If I went looking for that Laundromat stripper [today], I’d end up peering in the windows of a trendy bar with bookshelves and manual typewriters, where a pint of beer costs $7,” she wrote.

[MORE: Read our 2014 project on Portland’s big changes in recent years]

Seth has nearly a decade of professional journalism experience and writes about the greater Portland region.