It started as a birthday party for Rosendale bar owner Uncle Willy in 1978. The Rosendale Street Festival has grown into something much bigger since and is the 2026 Readers’ Choice Award winner for Music Festival. The original party had one stage playing music all day in celebration. This year, the festival has eight stages, including one named after Uncle Willy, and over 100 bands across a variety of genres, such as Modern Natives, They Like Rum, Unicorn Brass Band, and more.
Shutting down Main Street on the weekend of July 18-19, the festival is a large event that draws hundreds of vendors and thousands of attendees. It is a nonprofit grassroots organization that functions through the work of volunteers. “There’s a core group of 20 who work year round to make this festival a reality,” says Carri Wyckoff co-chair of the board of directors, “and we do it out of love for the festival and each other.”
The festival brings an economic boom to the city, with locals and tourists alike purchasing food, drink, and other goods at the event. “It brings thousands of people to Rosendale’s Main Street every year, so everybody can see our beautiful businesses and how much art and culture means to us,” says Wykoff.
The festival is free, so the costs are recouped through donations. “If we have enough money to pay all our bills and we’ve made a little profit,” says Wykoff, “we put it towards the Uncle Willy music scholarship we established.” The Uncle Willy Rosendale Street Festival Scholarship goes to graduating high school students from the New Paltz, Kingston, and Rondout school districts who are nominated by their music teachers.
This article appears in July 2026.
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