Jordan Wolowitz, left, of Shore Sound Entertainment and Tyler Grill of GoodWorks Entertainment, in Portland on Thursday, are hoping to bring a two-day live music festival to Payson Park. Derek Davis/Staff Photographer

A concert organizer has applied to host a two-day music and arts festival in Portland’s Payson Park in August 2025.

Name that tune? It might sound familiar.

In 2022, a major concert promoter submitted an application to the city for a festival in the park to mixed response. Some thought the event would boost local business, while others worried about the parking and the impact on the surrounding neighborhood. The sponsor – C3 Presents, a division of concert promotion giant Live Nation – ultimately decided not to move forward with the idea.

Now, a different team has proposed a similar but scaled-back event. The organizers are Tyler Grill of GoodWorks Entertainment and Jordan Wolowitz of Shore Sound Entertainment. Both are based in Connecticut and have worked for nearly 20 years in music festivals and live entertainment. Among their experiences, Wolowitz was one of the founders of the New York City-based festival Governor’s Ball, and Grill runs the Rhythm and Roots Festival in Rhode Island.

Now, they’ve set their sights on Portland. Grill and Wolowitz said they long enjoyed visiting restaurants and music venues in the city, and now they hope to create a festival here that would become an annual tradition. Their still unnamed event would bring 10,000 to 12,500 people per day to Payson Park. The first applicant hoped to attract as many as 20,000. A list of artists they offered as examples includes The Lumineers, Caamp, Steel Pulse, Brandi Carlile and Vampire Weekend.

“I’m confident that if given the opportunity, we can build something that is in Portland’s best interest,” Grill told the city’s Parks Commission on Thursday.

The permitting process is underway but still in the early stages. Grill and Wolowitz have been visiting Portland and meeting with local stakeholders. The Friends of Payson Park held a virtual community forum on the project in October. Andy Downs, the city’s public facilities director, and the organizers attended. Organizers presented their plans to the Parks Commission for the first time Thursday to a crowd of 20 or so observers. Thirteen offered public comment, nearly all expressing opposition or at least skepticism.

“You’re talking about 20,000 people over two days, which is a lot of people,” Devin Green said. “I’m for this event if it’s done well because I think it’s great for the city, but I think you need to consider, is 10,000 people a day really viable?”

The Parks Commission was split on its recommendation to the City Council, which will make the final decision. Five members of the commission supported a motion in favor of approval, and two opposed it. One member abstained.

Payson Park with its view of Back Cove and downtown Portland in April 2023. Contributed / City of Portland

Downs said the item has not been placed on an agenda yet but could be slated for December.

Their application says the target dates for what is tentatively named the Portland Music and Arts Festival are Aug. 2 and 3. A site plan shows that the festival would only include part of the park between Fernald Street and Baxter Boulevard. Most playing fields and courts would remain open to the public throughout the weekend. At the meeting, organizers outlined their plans for a bike valet, free bus rides and shuttles from parking lots, a ride share area and other steps to ease traffic in the neighborhood.

On both days, the proposal says music would start at noon and end at 10 p.m. An attached memo says the event will be “family focused and kid friendly” with free admission for children under 12 years old.

“The festival will feature nationally touring and local acts on two stages. Partnerships with local restaurants and food trucks will provide fans with the best local eats and craft beverages Portland has to offer,” the memo says. “Around the festival grounds local artists will be showcased through art installations and craft vending.”

Those who spoke raised questions about the impact on the nearby neighborhood, including Seaside Skilled Rehabilitation Center on Baxter Boulevard. A site plan includes two stages – one on the triangular field near Baxter Boulevard, one near the Payson Park Community Garden and very close to the nursing home.

Beyond the logistical concerns, the body also considered a more philosophical question about private use of public parks. Some residents and commissioners questioned whether a private company should be able to block off a section of the park and charge money for access to that space.

Teyonda Hall, director of resident services at the Portland Housing Authority, read a letter from the organization’s executive director expressing concern about the plan. She said the festival layout would block easy footpath access to the park for residents of the Front Street development, including dozens of children.

“Accommodating these higher-income park users at the exclusion of our residents does not seem to meet the city’s equity goals,” Hall read.

Grill said at the meeting that general admission tickets would cost $75, and a small number of VIP tickets would cost as much as $550. Downs said the organizers have agreed to pay $100,000 that would go toward a project of some kind in Payson Park, and the city would also receive $1 from every ticket. The festival would also be responsible for all city costs, including any restoration of the park needed after the festival.

“I want to get a bigger long-term picture across,” Grill said. “For us, we’ll lose money on this for about five years. As much as it could be perceived as this huge corporate gain, it really is not. … We are really making a major investment in a community when we come in.”

A ticketed event of this size on public property would be unique. In 2012, the British folk-rock band Mumford & Sons headlined a daylong festival on the Eastern Promenade that attracted more than 13,000 fans. The free annual fireworks show on July 4 attracts 20,000-plus people to the Eastern Promenade. Resurgam Music and Arts Festival, which is free and open to the public, brought 7,500 people to the Ocean Gateway Pier this summer.