The Wilmington Halloween Loop is dead.
But inside The Queen on a foggy Saturday night last October, the dead walked again.
And danced, and drank, and raged. This was the Halloween Loop’s 40th birthday party—a one-stop costume ball at the Market Street venue, and a departure from the bar crawl bacchanalia that became a Trolley Square tradition for generations of young revelers.
This time, the zombies and vampires that bopped around The Queen looked very much their ages, perhaps a bit softer and saggier than in their heyday. This version of the Loop truly seemed 40: a few more wrinkles, yawning and glancing around for the exits. The over-the-hill tombstone jokes practically write themselves.
Gerard “Jerry” duPhily, owner of TSN Publishing and publisher of Out & About magazine—who ran the Loop since 1988—acknowledges that it was time for the Loop to grow up. In 2018, just before closing time, violence and chaos erupted outside Kelly’s Logan House when a man fired a handgun into a crowd.
“The Halloween Loop, it’s just such an important symbol for the city and for the city’s nightlife,” he says months later while sipping an IPA at Maker’s Alley in Wilmington. “You mentioned the Halloween Loop to just about anybody in this state and they’ll smile, and they know immediately what you’re talking about, and everybody has a story. What was great about the new event is it gave people a chance to go back and live a little bit of their childhood.
“Times change. We have to kind of reinvent some things,” he continues. “But we’re bound and determined to keep the Halloween celebration and Wilmington’s celebration of Halloween going, however it evolves.”
The turbulence and subsequent pivot were nothing new to duPhily. He’s been helping to shape the city’s nightlife for more than 30 years, through good times and bad. The fit 62-year-old, who founded Out & About in 1988, has thrown his share of party clunkers. At the magazine’s launch party, held at a rented-out Brandywine Racetrack, hardly anyone showed. “We went in thinking we were Vegas entertainment moguls and oh, my God, it just was a colossal failure. Those were the most expensive beers I’ve ever had.”
But as usual, duPhily rebounded. As the leader of Out & About, he hasn’t just covered the city’s social scene. He’s helped created it. He’d led and curated some of Wilmington’s most signature events, including the Wilmington Grand Prix bike race, City Restaurant Week, Wilmington Beer Week and a stable of themed bar loops.
“I think Jerry is probably one of the preeminent champions for Wilmington,” says Julie Miro Wenger, a longtime local tourism and event staple who co-founded Event Allies with duPhily in 2005. “He’s worked on transition teams for mayors and has always been, and is looked to as, a staple for understanding what the needs of the community are at any given time. And he’s got historical perspective because he’s been doing what he does for so long, which is trying to move Wilmington forward and trying to promote what Wilmington’s really all about.”
Born in Wilmington but raised in Kent County, duPhily didn’t really get to party in Wilmington until college at the University of Delaware, where, as a senior, a friend brought him along to—where else?—the Halloween Loop, which was then run by music-centric magazine Fine Times.
After college, when duPhily found work as a sportswriter for a small weekly paper in Maryland, the budding journalist joined a recreational (though highly competitive) softball league and soon thereafter began publishing The Softball News, a DIY one-man show that covered the games and profiled the players. DuPhily sold and designed the ads himself, wrote the stories, created the layout, and pasted it all onto graph paper before printing and delivering it.
“I started thinking, I like being an entrepreneur. I like figuring this out,” he says.
While continuing to grow The Softball News, duPhily bounced around from gigs at The Coatesville Record, The Philadelphia Inquirer and The News Journal. Meanwhile, Fine Times, owned by brothers Dennis and Dale Milton, folded, leaving a void in the entertainment media ecosystem.
Along with co-owners Jim Bauerle and Paul Ogden, Out & About went into production in March 1988. Much of the early magic unfolded in duPhily’s DuPont Road home in Wilmington, where young staffers like Jim Miller clacked away on a Macintosh II computer about the beer specials and band schedules at neighborhood bars.
“I think from the start, I admired Jerry’s energy,” says Miller, now a 25-year Out & About vet. “He just had, and he still has, this very persistent, controlled and focused energy. Jerry is, in a lot of ways, a force of nature.”
Out & About picked up where Fine Times had left off, zeroing in on music and entertainment. But as Wilmington’s bar scene evolved throughout the ’90s, the magazine broadened its scope and duPhily channeled his energy into telling optimistic, community-minded stories.
“Early on, we took the philosophy of looking to where people were trying to do positive things in the community and we would try to amplify their efforts through the magazine,” he says. “We were writing about the local community and not just the people that became rock stars and went to Hollywood or became NBA players. It was Capriotti’s subs, it was artwork by Bill Renzulli, it was the Flower Market. It was local stuff, but there’s lots of good nuggets and great stories in local.”
Says Miller: “One of the most successful stories we ever ran was about Casapulla’s. It wasn’t this flashy exposé. It was about this family that had created a name for itself through making sandwiches.”
During Out & About’s emergence, Wilmington’s nightlife was changing. Police began enforcing stricter DUI laws as concerns over crime and safety grew. Trolley Square established itself as an appealing option for the bar crowd as more of Wilmington’s daytime workforce retreated to the unincorporated suburbs at dusk.
Prominent Wilmingtonians told duPhily: There’s just not enough happening in Wilmington for an entertainment magazine to succeed.
So, duPhily and Out & About took matters into their own hands. The magazine leveraged its name, its relationships and its marketing clout to organize a string of successful downtown events that coalesced around live music and cold beer.
There was the Bartender’s Ball, the Up On the Roof concert series (which welcomed bands like the Hooters, the Stray Cats and Blues Traveler to a literal parking garage rooftop), concert fundraisers for beach replenishment, and generally anything involving “that kind of organic energy and doing stuff in funky places,” duPhily says.
In 2005, duPhily forged a new company along with Miro Wenger called Event Allies, and the following year helped launch the Wilmington Grand Prix. The pair knew what it would take to make the bike race a success: namely, trust and buy-in from city officials, local businesses, advocates and volunteers, and a whole lot of sweat equity. They built bridges with community partners and banked a war chest so they could pay professional cyclists to participate.
“We never wanted to go about creating a bike race for the sake of creating a bike race,” Miro Wegner says. “It was an event that was intended to create pride for people that work and live in the city of Wilmington and the state.”
Today, the Grand Prix earns local and national plaudits. Since 2012, it’s generated more than $4.5 million in economic impact for the local economy, according to its website.
While duPhily-adjacent events helped transform Wilmington’s cultural scene (and planted the seeds that grew into the renaissance that’s unfolding downtown today), his flagship magazine has mainly stuck to its roots.
As the internet and smartphones forced media companies big and small to reinvent themselves—through podcasts, digital editions, apps and livestreams—monthly Out & About has held steadfast as a print-first product (though it does maintain a clean but modest website). It’s always been free, and in 32 years, duPhily has never missed a deadline.
“It’s almost like vinyl,” he says. “There is a non-invasiveness, there’s a liberty, there’s a freedom with print. You read the story that you want to read. There’s nothing popping up on the screen. You can lay it out and read it, you can wrap it up and swat the fly and continue reading. You are in 100-percent control of print and that’s not the case in the digital world.”
Out & About continues to survive by doing what it does best, duPhily says. Competitors—from Big Shout to Spark—have come and gone. But Out & About stays in its lane by leaning into the events, issues and talents that make its community unique. Well-known contributors over the years included photographers Jim Graham and Fred and Butch Comegys, food columnist Patricia Talorico and longtime writer/grammar stickler Bob Yearick.
“Sometimes it has felt like we’re the teacup in the storm,” says Miller. “We’ve had almost every catastrophe: The office got flooded, the servers have gone down, a computer virus hijacked information from us—and somehow, we’ve survived. In that sense, Jerry has really been the captain of the ship.”
As the Halloween Loop shows, duPhily and Out & About can weather just about any storm, adapt if needed, and come out stronger on the other side. “History does repeat itself,” he says. “You can learn from the past, but that doesn’t mean you can’t reinvent.”
The history lesson here in lifting up a city? To quote duPhily, “Recognizing an audience and adding energy to their passion.”
Published as “Life of the Party” in the July 2020 issue of Delaware Today magazine.