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

Most artistic directors curate seasonal calendars for traditional theaters, historic opera houses, or municipal auditoriums. Zack Winokur, however, commands an entire floating sanctuary in the Hudson River.

For the past three seasons, Winokur has held the role of producing artistic director at Little Island, the architectural marvel and public park anchored near Manhattan’s Meatpacking District that opened its piers five years ago.

A Juilliard alumnus with a rich background in directing and producing theatrical and operatic works—including co-founding the visionary American Modern Opera Company in 2017—Winokur approaches Pier 55 unlike any conventional venue. Positioned entirely outdoors on an artificial island, the space offers visionaries a rare canvas to design cohesive audio-visual environments across a distinct open-air landscape, far transcending standard park performances.

The current season showcases bold new ventures from returning avant-garde luminaries—such as Justin Vivian Bond launching the calendar with Summer’s Eve, Anthony Roth Costanzo charting minimalist musical milestones, and Laurie Anderson collaborating on Thomas Bartlett’s Allen Ginsberg at 100—alongside homages to New York’s deep-rooted musical heritage. Bandleader Louis Cato channels the vibrant energy of the Harlem Renaissance and the Savoy Ballroom, while multi-Grammy winner Cécile McLorin Salvant reimagines the timeless boundaries of Tin Pan Alley.

Furthermore, genre-defying creators continue to imprint their unique aesthetics onto the island. Tony Award winner Qween Jean hosts the dazzling Summer Legacy Ball, while Julio Torres and Martine Gutierrez present the premiere of Marina—an aquatic fairy tale exploring intimacy, identity, and modern illusions commissioned by the 2026 Whitney Biennial.

Complementing the ticketed performances, the Brooklyn-based DJ and art collective Papi Juice hosts vibrant, inclusive dance parties in the park’s “Play Ground.” Strategically aligned with evening events at The Amph—Little Island’s 700-seat amphitheater—these gatherings invite audiences to seamlessly transition from a seated concert to open-air dancing under the stars.

Ahead of the 2026 season kickoff, Billboard sat down with Winokur to discuss his curatorial philosophy, what audiences can expect this year, and why these dynamic evenings evoke the spirit of legendary broadcasts like MTV Unplugged.

To begin with, how did you step into this distinctive leadership role?

It developed through a wonderfully winding path. Before the park was fully constructed, my colleagues and I at the American Modern Opera Company (AMOC) were exploring potential collaborations for the site, though those initial plans didn’t materialize immediately. During the park’s inaugural summer, Mikki Shepard curated an extraordinary, expansive multidisciplinary festival. My company performed a celebration of Julius Eastman’s music on the closing night. Afterward, media mogul Barry Diller reached out to discuss a fresh curatorial vision, which ultimately evolved into our current model of commissioning original programming. I officially launched my inaugural season in 2024.

When you first met with Barry Diller, was there a foundational philosophy guiding your vision?

We shared an immense excitement around integrating high-caliber performance art directly into a public park setting—an inherently magical proposition. Our primary goal was to bridge high art and accessible public culture, keeping ticket prices modest at a maximum of $25 while offering numerous free events. I’ve always been drawn to exceptional artists whose work is deeply informed by New York City. Much of our programming is designed to let historical icons and contemporary innovators collide in a singular, inspiring ecosystem.

How would you define the core audience for Little Island?

The audience mirrors the diverse demographic that visits the park daily. On peak summer days, we welcome upwards of 13,000 visitors just enjoying the grounds. While the island has rightfully become an iconic international destination, it also functions as a vital neighborhood park where local runners and families cross paths every morning. My ongoing priority is ensuring the programming feels welcoming to all New Yorkers without ever feeling exclusive.

How do you map out an entire season? Are you constantly scouting talent across the five boroughs?

It’s a deliberate blend of discovery and collaboration. I’m constantly looking for artists who challenge expectations or are willing to venture beyond their usual creative parameters. We honor New York’s cultural lineage by bringing back icons like Twyla Tharp, Qween Jean, Charles Ludlam, and Justin Vivian Bond, alongside monumental explorations like Meshell Ndegeocello’s interpretation of James Baldwin. We even celebrate hyper-local history, such as nodding to Florent, the legendary Meatpacking District diner that defined an era.

You’ve previously collaborated closely with Justin Vivian Bond. When working with artists who return each season, how do these concepts take shape?

With recurring collaborators like Anthony Roth Costanzo, the dialogue is remarkably organic. Our work together on Figaro—where Anthony performed every vocal role—began as a playful backstage joke during a tour in Dublin. When another production had to reschedule, we seized the opportunity to realize that ambitious idea on the island. This season, focusing heavily on music, we are exploring a maximalist approach to minimalism, celebrating Philip Glass, Julius Eastman, John Adams, and Meredith Monk through a grand orchestral lens.

With Viv, the creative process is an endless adventure. This year’s concept originated from her deadpan remark: “I’ve always wanted a show where everyone performs on fainting couches.” We partnered with designer Adam Charlap Hyman to craft custom velvet loungers for Viv and her band, while Dries Van Noten designed their bespoke wardrobe, setting the stage for a wonderfully relaxed performance style.

Given intense summer heat waves in the city, how challenging is open-air programming?

It certainly presents unique hurdles, and severe weather like lightning storms requires safety cancellations. Fortunately, our evening schedules generally offer a manageable climate. Moreover, Little Island holds a liquor license across the entire park, allowing guests to enjoy specialty cocktails and refreshments alongside artisanal lemonades, turning weather mitigation into part of the venue’s relaxed charm.

What key insights about the physical space have influenced your approach to future seasons?

The amphitheater features a thrust stage, creating profound intimacy despite holding over 700 seats. No audience member is ever far from the performer. Furthermore, our integrated park-wide sound system ensures that visitors strolling along the pathways can experience the music even if they don’t hold a ticket. The absence of traditional theater walls allows the entire 2.4-acre park to function as a unified public living room.

How do performances like Cécile McLorin Salvant’s Tin Pan Alley showcase and Louis Cato’s Harlem Renaissance tribute resonate with modern audiences?

This foundational music continues to influence contemporary culture profoundly. Cécile possesses a peerless ability to elevate lesser-known B-sides into anthems, much like Nina Simone used to do. Meanwhile, Louis Cato highlights visionary composers like Fletcher Henderson, spotlighting the massive historical energy of historic dance halls like the Savoy Ballroom.

What does your daily routine look like during the peak of the festival season?

It is an immersive, round-the-clock experience. A typical day involves checking in with visiting artists, refining production schedules, inspecting stage layouts, and conducting walkthroughs with lighting and set designers alongside our dedicated production team. Being present for nearly every evening performance is an immense privilege, allowing me to fully experience the vibrant intersection of music, community, and open-air theater in New York City.

Leave a Comment

Your email address will not be published. Required fields are marked *

Name *

Email *

Website

Post Comment

 

Source