Rendering / Courtesy Barrett Made
The space was ripe for build-out, with 22-foot ceilings and two units of 4,000 and 6,000 square feet on a single floor.
Updated: May 26, 2025
New live-music venue proposed for the Old Port
Rendering / Courtesy Barrett Made
The developers submitted plans to the city to turn a 10,000-square-foot lease at 144 Fore St. into Live at Madrid’s.
The developers of a proposed year-round, live-music venue in Portland’s Old Port neighborhood expect to fill a hole as a mid-size platform for local and regional artists, and even serve as a feeder to the area’s larger showcases.
Josh Schlesinger leased 10,000 square feet at 144 Fore St. He and his partner in the venture, Rob Barrett of Portland architecture and construction firm Barrett Made, submitted plans to the city to build it out as Live at Madrid’s.
Jennifer Davies and Steve Baumann of Compass Commercial Brokers brokered the deal.
The building, which is 43,210 square feet in all, is owned by 144 Fore St. LLC. Dating back to 1963 and renovated in 1990, it’s located at the base of Munjoy Hill on the East End, in an area that’s been undergoing revitalization projects in recent years that include construction of hotels and the headquarters for fintech service provider WEX Inc. (NYSE: WEX).
Right size, right zone
“Spaces of this size in the right zone are hard to find,” said Davies, who represented Schlesinger in the deal. “I knew that the zoning was perfect for the use and the ceiling height at 22 feet was a big factor for him. Parking and the fact that it is sort of off to the eastern side of the Old Port also had a lot of appeal for patrons, traffic and ease of access. Noise would also not be an issue at this location.”
As is the case in many transactions, relationships were key. Davies and Schlesinger met when they both served on the board of the Maine Academy of Modern Music.
"Jeff Shaw, the executive director, was the one who actually told Josh to give me a call to help him find and lock something down,” she said. “The landlords was also looking for this type of use for the building, so it really all came together.”
Maine Academy of Modern Music is another tenant in the building, in a 2023 lease deal that was also brokered by Davies and Baumann.
Hospitality veteran
Schlesinger grew up in central New York and has been in the hospitality and food and beverage industries for almost 30 years: he was 14 when he started working in restaurants.
He moved to Portland in 2002, worked for seven years at Sebago Brewing Co. and has been a bartender for the Thirsty Pig in downtown Portland for the past six months or so.
Since 2014, he’s run sales for Bissell Brothers Brewing Co. in Portland. For some of that time, he had own distribution company, Sleek Machine Distro — named after lyrics from Bruce Springsteen's “Jungleland.” He’s still doing deliveries four days a week and bartending at the Thirsty Pig on Friday nights.
“The rest of the time is cobbling together this project,” he said.
Music fan
Schlesinger has always been in and around music, mostly as a fan and a consumer. He and his wife have been kicking around the idea of starting their own music venue for about five years and started hunting for a space in early 2024.
Rendering / Courtesy Barrett Made
The developers expect to fill a hole as a mid-size platform for local and regional artists and serve as a feeder to the area’s larger showcases.
“It was one of those conversations that went, ‘It’s either now or never,’” he recalled. “Then came exploratory phone calls and conversations. One thing led to another.”
He built out a rudimentary financial forecast and business plan and contacted Barrett to help patch together build-out numbers.
“He’s been a tremendous help as an entrepreneur, a friend, an owner, an employer, a local businessperson,” Schlesinger said.
Filling a hole
Much of the goal is to fill a hole that the July 2020 closure of Port City Music Hall, a performance space in Portland’s Arts District, left behind, he said.
“When Port City went away, there wasn’t a mid-size venue in Portland anymore, or even in the area, that was doing the things needed in a market like this, which is to give local artists a platform,” he said.
Photo / Courtesy Cam Jones
Josh Schlesinger and Rob Barrett propose building out an empty shell into a live-music venue.
Schlesinger had just sold Sleek Machine and “was unusually cash-flush.” When Port City closed, he put in an offer on the property, but the deal didn’t go through. After looking at other spots, he landed on 144 Fore St.
The site was good for a number of reasons, he said. It’s across from the waterfront and surrounded by hotels that would likely result in customers, within walking distance to the Old Port and there are no homes nearby. Parking is available at the landlord’s nearby garages.
“A big part of finding the right space was having parking,” said Schlesinger.
It was ripe for build-out, with 22-foot ceilings and two rectangular units of 4,000 and 6,000 square feet on a single floor.
“We envision an 800-person capacity, live-music venue” — about 30% more capacity that Port City, he said.
The venue would also be offered for corporate functions, weddings, community events and small trade shows.
A lot of bands in the Northeast don’t have venues appropriate to the smaller size of audiences they attract, compared with national artists, he said.
At the same time, he said, Live at Madrid’s could serve as a feeder or test room for local and regional artists to larger venues like the State Theater, which offers live shows at 609 Congress St.
“It’s not that we see something that we can do better,” he said. “It’s that we see a hole that needs to be plugged. We have the connections in the Maine and the Portland markets to plug the hole.”
So far, Live at Madrid’s team includes Cam Jones, a musician and friend, to do the marketing, and Meg Shorette, a long-time arts professional, as booking manager. Jack Murray, owner of Ocean AVL (audio, video, lighting) in Portland, is running point on the install of sound and lights as well as the acoustic treatment of the room.
Pending city approvals, Schlesinger is shooting to open by January 2026. Already, he’s getting calls from bands and from folks looking for wedding venues in 2026.
Schlesinger declined to cite investment into the project, which was approved for a loan from Norway Savings Bank. Schlesinger launched a fundraiser with a goal to raise $500,000 for the build-out. The landlord is financing much of the exterior work, he said.
Barrett is finalizing the floor plan. The partners submitted their plans to the city in mid-May. The hope is to break ground on the interior before August.
The work would include building a main stage and bar and a side stage and bar, green rooms, office space and a big patio out front.
“Yes, this is a passion project,” he said. “But above all else, this is a business decision predicated upon the recognition of a glaring hole in the midsize venue market. I try to see live music as much as I can. Being an entrepreneur and a small business owner and working in that space in Portland, you can see where the holes are in the market.”
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