Little Island, Big Ideas: How New York’s Most Unusual Outdoor Venue Crafts Its Lineup

Some artistic directors determine the seasonal programming for a theater, opera house or community space. Zack Winokur, however, has an island unto himself.

For the last three seasons, Winokur has served as the producing artistic director of Little Island, the artificial island/public park adjacent to Manhattan’s Meatpacking District in the Hudson River which opened five years ago.

While the Juilliard-educated Winokur had directed, produced and/or cocreated theatrical and opera productions prior to this gig (he also co-founded the imaginative American Modern Opera Company in 2017 and serves as its artistic director), Little Island at Pier 55 is unlike any other performance space in a city that has no shortage of them. Not only is it outdoors, but, as the name suggests, it’s a literal island. Unlike, say, theatrical performances in Central Park, Little Island presents artists and innovators with the opportunity to shape the audio-visual experience of an entire discrete outdoor space.

This season, Little Island features new works from returning musical iconoclasts (Justin Vivian Bond opens the season with Summer’s Eve from July 29-31; Anthony Roth Costanzo takes a tour through minimalist music history from Aug. 5-9; Laurie Anderson participates in Thomas Bartlett’s Allen Ginsberg at 100 from Sept. 2-6) as well as excavations of New York City’s rich musical foundations (The Late Show with Stephen Colbert bandleader Louis Cato brings the music of the Savoy and Harlem Renaissance back to raucous life from Aug. 19-23; three-time Grammy winner Cécile McLorin Salvant explores the edges of Tin Pan Alley from Aug. 12-16).

Additionally, creative trailblazers are bringing their distinct visions to the island. Tony winner Qween Jean throws a Summer Legacy Ball extravaganza on Aug. 1, and from Aug. 27-30, Julio Torres and Martine Gutierrez premiere Marina, “an underwater fairytale about love, belonging and catfishing” (what else would you expect from the boundary-free brain of Torres?) commissioned by the 2026 Whitney Biennial.

Throughout the entire season, Papi Juice parties — thrown by the Brooklyn DJ/art collective centered around uplifting queer and trans people of color — will bring free dance parties to the island’s “Play Ground.” The Papi Juice parties always dovetail with one of the performances at The Amph, Little Island’s 700-plus-seat amphitheater – meaning you can catch a show, grab a drink and shake your thing all on the same night on the same island.

Ahead of Little Island’s 2026 season, Billboard spoke with Winokur about how he approaches programming the bespoke space, what we can expect from this year’s slate and why certain Little Island performances remind him of MTV Unplugged or “the parade of animals going to the Big Apple Circus.”

To begin with, how did you end up landing this role?

It actually is a weird, circuitous route. Before the park was built, I was starting my own company, the American Modern Opera Company, AMOC, and we were in conversations to do a show well before the park was built. That never happened. And then when it opened in the first summer, Mikki Shepard ran this really beautiful free festival that was super dense — I think it was just one month, but just gigantic. And my company did a show of all Julius Eastman’s music that was the closing night of the opening festival. Then Barry Diller [billionaire businessperson who commissioned Little Island] called me and asked me to think about a new approach to programming, and we came up with this thought of doing more original programming. I started my first season in 2024.

Was there a thesis when you were talking to Barry? Was there a unifying idea to the kind of things you were looking for?

I think the thing that we were most excited about, and certainly I was most excited about, was a couple of things. One is that we so rarely think of performance as part of public art, and the idea of doing shows in a public park feels incredibly special. So one of the points was to bring a real high-low sensibility to a public space and to make it as accessible as possible, which is why so much of our programming is free and the maximum ticket price is $25. And I was always really interested in extraordinary people, and people particularly who live here or are inflected by the city in one way or another. I think so many of the things that we’re doing this year, and that we’ve reflected on in the past, are about different scenes or icons from the past, the present and the future, all colliding in one place on the island. If that makes sense.

It does. In terms of audience, who is Little Island programming for?

I think it reflects who visits the park, actually, which is always a very interesting thing. In the summers we have days that are 13,000 people just visiting the park without performances happening. What’s interesting about it is that it has quickly become an iconic place in the city, and therefore it’s a very popular destination for tourists. But it’s also a neighborhood park. You see the same people running through it, the same families coming through every morning. That was the thing I’m thinking about all the time in terms of the programming as well — that it should be attractive to anybody, and it should feel like a space that is extremely for New Yorkers without being exclusive at all.

How do you figure out the season? Are you looking at performers around the city and thinking, “I like what they’ve done in the past, so let’s talk with them about what they might have coming up”?

It’s a mixture of things. I’m always on the lookout for people who surprise me. I’m also always interested in asking people who I just think are extraordinary to do something a little bit further to the edge of what they normally do — and also putting back into the center things that are on the edges. So I think about this sense of the neighborhood and its icons — thinking about past seasons with the likes of Twyla Tharp and Qween Jean, who’s returning, and Charles Ludlam and Justin Vivian Bond, who is a scene all to herself, and even Meshell Ndegeocello taking on Baldwin [in 2025]. These are all people exploring moments that defined New York, and that also might define the future of our city. Even things like this season — we have Florent coming to the island, who had this extremely famous diner in the Meatpacking District [from 1985-2008]. So also things that are also hyper, hyper local.

You brought up Viv. You were one of the co-creators of Only an Octave Apart, a show that turned into an album I absolutely adore. With someone like Justin Vivian Bond or Anthony Roth Costanzo, who have been at Little Island every season with you so far, do you just call them up and say, “Got any ideas?”

I think with Anthony in particular — people who I’ve worked with for so long — it is a pretty organic conversation. The first project with Anthony was kind of a hilarious accident that came out of our work in Only an Octave Apart, where he does the male and female parts of this Figaro duet. By the 50-something-odd performance, we were in Dublin, and he was doing the show, and afterward I was joking with him. It started as a bit and then it just got really good. I said, “Maybe one day we should do all of Figaro — where you sing every role.”

Then I was working on a show for my first season that dropped out because someone got a really fabulous arena tour, and I called Anthony and said, “What if we actually did it?” We spent a couple of days trying to figure out whether there was a way to edit it down so that he could actually survive, and then we just endeavored to pull it off. That was extremely fun.

Similarly, thinking about him in the context of Maria Callas with Charles Ludlam [Galas] last year. And for this year, because we really are focusing on music, I was interested in — obviously he’s had a very big moment with minimalism, particularly with the music of Philip Glass, with Akhnaten and also Satyagraha with another person I work very closely with, Bobbi Jene Smith, who’s also been on the Island, who directed the Satyagraha in Paris. So he’s doing the entire trilogy.

I was wondering if we could think of a kind of maximalist version of minimalism — his version of not just Philip Glass, but also of [Julius] Eastman and John Adams and Meredith Monk. Could we bring in Moondog, could we bring in Steve Reich, and who were all the other people? He’s really been, as always, just a fabulous thought partner in reaching toward these unexpected edges of the genre that he, in this moment, is coming to define in some way.