Once Upon a Time at Madrid’s
arts & culture
words by casey oakes | photos by cam jones
Welcome to Live at Madrid’s. The name isn’t Spanish, not nautical, and not another riff on Maine. Owner Josh Schlesinger pulled it from a minor character in Quentin Tarantino’s film Once Upon a Time … in Hollywood. “When you hear Madrid’s, you’re intrigued,” he says. “That sense of intrigue has always been the point.”
On March 13, 2026, Live at Madrid’s opened its doors for the first time with a sold-out performance by Gina and the Red Eye Flight Crew, an energetic nine-piece band drawing members from other well-known bands, such as Rustic Overtones. With a huge mural, featuring a logo by branding and design firm Might & Main and painted by muralist Ryan Adams, this Fore Street venue is as eye catching as it is ear catching. Schlesinger believes music is best experienced up close and rooted in community—although his path to opening Madrid’s didn’t come up through the music scene. He moved to Maine in 2002 to attend the University of Southern Maine, and Portland quickly became home. In 2006, he was rooming with Peter Bissell, back when “we survived almost entirely on Orloff and Diet Coke,” and long before opening a brewery had entered the conversation.
By 2013, Schlesinger learned how to build a business from the ground up at Bissell Brothers, working alongside founders, Peter and Noah Bissell. Those early years of the craft beer boom delivered a crash course in startup life, defined by long days, shared risk, and growth guided by intention.
When Port City Music Hall closed in 2020 at the height of Covid, Schlesinger made a “lowball offer” to take over the space. He didn’t get it, but the spark was lit. “I wouldn’t be doing this project if Port City Music Hall was still here,” he says. “I saw a hole in the market, and I’m plugging it.”
He thought that if he could survive sleepless nights with his new baby, he could handle opening a music venue. Somewhere between exhaustion, ambition, and a deep love of live music, Madrid’s was born.
Stepping from the service industry into the music world, Josh entered uncharted territory, and he knew he needed the right people to make Madrid’s a reality. Early support from Lauren Wayne of the State Theatre and Thompson’s Point helped shape the plan. Amber Card from Portland House of Music oversees front of house; Meg Shorette handles booking; Jack Murray at Ocean AVL outfits lights and sound; and Rob Barrett and Barrett Made shaped Madrid’s interior identity alongside project manager Andy Stephens. John Duncan's photography fills the space and hangs prominently over the bar. Cam Jones, a Maine musician, leads branding and has become Josh’s closest guide.
“Cam is the true insider,” Josh says. “He let me ask stupid questions, be vulnerable, and learn the industry from the inside out.” With that team in place, Madrid’s is already hosting major events including The Ghost of Paul Revere, The Mallet Brother’s Band, and Portland Ovations’ annual fundraiser celebration, POP.
After initially touring the former World Gym, now Minibar Golf, as a potential home for Madrid’s, Schlesinger ultimately chose a former boat repair facility that doubled the project’s scope. Given the investment, Madrid’s needed to be a must-stop venue for Northeast tours, polished and professional, from day one.
With an 800-person capacity, full bar, and a genre-less stage, the space hosts everything from hardcore and hip hop to folk, DJs, singer-songwriters, rock bands, drag artists, special events, and Pride celebrations. “Literally anyone can take the stage,” Josh says, “as long as they’re respectful of the community and engaged in the human connection.”
That focus on connection appears everywhere, from the nostalgic signage to Schlesinger’s philosophy about the room itself. “Humans get to be human together at Madrid’s,” he says. “There have to be humans on stage and humans in the audience.” The culture Schlesinger helped build at Bissell Brothers continues to guide how he leads at Madrid’s. He treats people like people, resists following rules blindly, and prioritizes his team. “My staff are real people first,” he says. “At the end of the night, it’s my job to carry it home.”
Check out upcoming shows at liveatmadrids.com
