There are Pride parades, and then there’s Pride suspended 212 feet above a tidal river, with the wind coming off the Hudson and the Catskills and Taconic ridgelines framing the horizon. “Pride in the Sky,” returning May 30 to Walkway Over the Hudson State Historic Park, has established itself as the Hudson Valley’s most visually arresting kickoff to Pride Month—a celebration that trades asphalt for altitude.
Now in its third year, the free event is a co-production of Big Gay Hudson Valley, Friends of the Walkway, and the New York State Office of Parks, Recreation and Historic Preservation. More than 7,000 people attended across the past two years, and organizers expect even larger crowds this time around. The format remains expansive: simultaneous community festivals on both the Highland and Poughkeepsie sides from 3 to 10pm, converging at dusk for a procession and dance party at the midpoint of the bridge.
“Pride In The Sky is one of the most powerful expressions of what this park can be—a space where community, joy, and belonging come together in a truly unforgettable way,” says Friends of the Walkway Executive Director Lori Robertson. “We’re proud to partner with Big Gay Hudson Valley to create an experience that is welcoming, inclusive, and accessible to all.”
Photo: Tanner Townsend
For Stephan Hengst, the event is a natural extension of nearly two decades of community-building. “Big Gay Hudson Valley has been building and connecting communities for almost 20 years,” he says. “With the Walkway serving as a stunning connector for both sides of the Hudson River, it’s the perfect place to come together for a massive free event like Pride In The Sky. During these times when too many leverage our differences to divide our communities, Pride events throughout the Hudson Valley spread queer joy while offering the perfect opportunity to showcase how our diversity brings us together.”
This year introduces a new element: the Queer Families Festival on the Poughkeepsie side, running from 3 to 6pm in partnership with the Dutchess County Pride Center. The lineup leans intergenerational—Drag Story Time with Katarina Mirage, kids yoga from The Yoga House, art activities from The Art Effect, and an ice cream social designed less as spectacle than as connective tissue. It’s Pride reframed not only as celebration but as infrastructure—something that supports everyday life.
Across the river in Highland, the tone skews toward performance. A community festival anchored by food trucks and a beverage garden sets the stage for a run of live acts, including Will Reynolds and Jen Malenke’s Broadway in Beacon showcase, followed by a preview from the upcoming musical adaptation of Alison Bechdel’s “Fun Home.” As evening settles, Andramada and the Dutchess County–based House of Drama bring their high-camp YAS DIVA energy before the decks turn over to DJ Gadget.
But the defining image of the night arrives at dusk, when more than 200 volunteers carry two enormous Pride flags across the span. One is a 100-foot rainbow flag created by Gilbert Baker for the flag’s 25th anniversary in 2003; the other, unveiled last year, is a 125-foot transgender Pride flag produced by Big Gay Hudson Valley with support from more than 300 donors. The procession moves slowly, deliberately—less parade than pilgrimage—until both banners meet at the center of the bridge.
From there, the event pivots into what organizers call “Disco 212 Ft in the Sky.” DJ Prephab takes over, turning the walkway into an open-air dance floor suspended between two counties, two shorelines, and a couple of centuries of Hudson Valley history. The symbolism is not subtle: connection, visibility, movement.
Pride in the Sky has, in short order, become one of those events that feels inevitable in retrospect. The Walkway—once a railroad bridge, now a linear park—was always going to be a stage for something like this. The only surprise is how quickly it has filled that role, drawing thousands into a shared space where celebration and landscape reinforce each other. Pride, here, doesn’t just march. It crosses.
