New Arts And Music Festival Could Be Coming To Stamford

STAMFORD, CT — One of Stamford's signature events, Alive at Five, is not returning for 2025, but a new music festival could be on the horizon for the city.

Tyler Grill, the co-founder and managing partner at GoodWorks Entertainment, and Jordan Wolowitz, the owner of Shore Sound Entertainment, are proposing the Cove Island Music & Arts Festival for May 30-31, 2026, at Cove Island Park.

A presentation on the proposal was included in agenda materials for the April 16 Parks and Recreation Commission meeting, but members felt a larger special meeting would be more beneficial.

A special meeting has been scheduled for May 7 that will include festival organizers, the Board of Representatives Parks & Recreation Committee, as well as other stakeholders and representatives from the police and fire departments.

According to the presentation, Grill and Wolowitz, who are both Connecticut natives, said "there is now a void within the city for live music/entertainment events" now that Alive at Five has ended.

The two noted in the presentation that they have owned and produced many festivals and concerts in the region, ranging from small towns in Rhode Island, to New York City and the popular Governors Ball Music Festival.

Wolowitz co-founded Governors Ball in 2011. The event has featured artists like Billie Eilish, Drake, Kendrick Lamar, Post Malone, and Kacey Musgraves, among many other notable names.

"We have a deep understanding of what is involved to ensure a safe and successful event in markets very similar to Stamford - and it starts with building effective partnerships with municipal stakeholders, first responders, and community leaders," the presentation noted.

Grill and Wolowitz say the festival would draw people from across the state and wider region, which in turn will drive weekend hotel stays and impact the local economy through restaurants, coffee shops and other local businesses.

According to the presentation, the proposed location for the festival is Cove Island Park, although Parks & Recreation Commission Chair Melanie Hollas said they'd be OK with Cummings Park as a backup.

Gates would open at 12 p.m. with music from 1 p.m. to 10 p.m. The target age for the festival is 35 to 65, and "family focused and kid friendly" with free admission to those age 12 and under.

Artist examples include Dave Matthews Band, Steel Pulse, Brandi Carlile, Christone Kingfish Ingram, Trampled by Turtles, Black Pumas, Gary Clark, Jr., Trey Anastasio, Nathaniel Rateliff, Ben Harper, Kamasi Washington, Charley Crockett and Margo Price, according to the presentation.

Hollas said she wanted more clarity on the amount of people expected for the two-day festival.

The presentation notes a capacity of 20,000 to 25,000 people per day.

"Before we were told it was 10,000 to 12,000 per day," Hollas said. "That's a big difference."

The presentation also outlines plans for parking and transportation, waste management, public safety and park maintenance.

Notably, Grill and Wolowitz say a financial contribution would be made to the parks as part of efforts to give back to the community.