Ian Cross

You know how some people, when they talk about meeting the love of their life, say something like, “I just knew, by the end of the night, that this was the one”?

Ian Cross sounds like that when he talks about his first-ever visit to Philly.

The year was 1987, he was living in Boston at the time, and he and a friend decided to take a road trip south, with no destination in mind. By the time they hit Philly, they needed a drink and pulled off I-95 right into gritty, pre-gentrified Old City, where they landed at the tavern inside the Society Hill Hotel at 3rd and Chestnut.

The place was packed with fun and friendly people, the bartender was fresh-squeezing O.J. into the screwdrivers, and Cross was reveling in Philly’s blend of gritty warmth and charm when a commotion on the street pulled everyone outside.

“People were yelling, ‘George Bush’s motorcade is coming down the street!’” says Ian. The then-vice president was in town for some kind of celebration (likely the Constitution Day festivities, which had drawn political protesters in the historic area), and as he passed the hotel, the crowd hurled insults at him.

“Everyone just was so full of energy, and it could have gone either way, positive or negative – it was fantastic! The city just got inside me right away,” laughs Ian, 61, a British ex-pat who grew up in Marlborough, England, and landed in Boston for work.

He officially moved here at the end of 1989, married a local, and eventually settled in Old City. In 2003 they bought the building that houses the Trestle Inn, the circa 1900’s tavern that was still in operation at 11th and Callowhill Sts.

“In Philly, there are certain places where you can feel the stories in their walls, and you just want to find out what they are,” he says.

If the walls of the Trestle could talk, they’d tell tales about its days as a seedy lounge where factory workers and journalists bellied up to the bar while mostly naked dancers entertained the rowdy patrons, who were ordered to keep their hands to themselves.

In 2011, Ian and his wife took over management of the bar, which was in dire need of renovation. As they reimagined the place, they wanted to honor what they’d always loved about Philly itself: muscular music, communities, and characters. That’s why the Trestle leans heavily into ‘60s and ‘70s soul and funk, with vintage whiskey cocktails and (fully clothed) go-go dancers whose energy matches the loose vibe that seduced Ian when he sipped that first screwdriver at The Society Hill Hotel.

He likens Philly to places like Manchester in the north of England, cities built on industry that later reinvented themselves through arts and culture. “You can feel that same undercurrent of creativity in Philly,” he says. “And potential – always potential.”

He embraces our city’s clichés. Yeah, it’s in-your-face, its edges can be rough. But it also has depth and resilience, which make it such a bracing, interesting, and endlessly satisfying place.

“Too many cities are antiseptic,” Ian says. “They’ve got a nice veneer, but when you peel it back, there’s not much underneath. Philly’s not like that.”

Outsiders, he says, “think it’s all Liberty Bell and Independence Hall. But if that’s all they see, they’ll miss what makes this city rich – the neighborhoods, the people, the stories.”

That’s why, if a tourist were to ask Ian for recommendations of spots to visit, Ian wouldn’t offer the usual list of sightseeing stops.

“I’d tell them to get out, walk around. Hit a corner bar,” he says. “Talk to people, explore, and let the city unfold. You never know what story you’ll stumble into.”