Downtown Oswego's Washington Square Park is packed this weekend with live bands, food trucks and craft vendors as the Central New York Pumpkin Festival returns for its two-day run. The free festival runs from 11 a.m. to 6 p.m. Saturday and 11 a.m. to 5 p.m. Sunday, drawing families to the park many locals still call East Park. Behind the bounce houses and character meet-and-greets, the weekend also serves a more serious purpose: it is the main annual fundraiser for one of the oldest YMCA branches in the country.
Oswego YMCA Executive Director Cheryl Baldwin joined Spectrum News's In Focus with Jodee Kenney to preview the festival's return, discussing both the weekend's family-friendly entertainment and the YMCA's broader role in the region. The festival includes food, local vendors and activities throughout the weekend, according to the Spectrum News report, and organizers say it takes a coordinated effort from local businesses, sponsors and volunteers to pull off each year.
That collaboration shows up in the festival's backers. The event is produced by the Oswego YMCA with operational and corporate support from the City of Oswego, Charter Communications, Constellation, and the Children's Board of Oswego, according to a Facebook post from Oswego County News Now. That mix of municipal and corporate backing has helped keep the gathering free and open to anyone who wants to wander through the park.
Music Lineup Spans Two Days
Saturday's entertainment features Dirtroad Ruckus and Frostbit Blue, with Seth Rasmussen & the Rail Ramblers and the Jess Novak Band taking over the stage Sunday, per a schedule listed on CNY Alive. Festival programming also includes bounce houses, local craft vendors, food trucks and character meet-and-greets, all with free public admission to the park, according to a column published by Oswego County Today.
The festival has become a fixture of the fall calendar in downtown Oswego, with earlier iterations involving joint planning alongside local business chambers.
Fundraising Ties to a 170-Year Legacy
The festival is more than a seasonal gathering for the Oswego YMCA. It serves as a primary annual fundraiser supporting community programs and family services at the organization, according to reporting from Spectrum News journalist Jodee Kenney. Founded in 1855, the Oswego YMCA marked its 170th anniversary in November 2025, making it one of the oldest operating YMCAs in the United States, per Oswego County Business Magazine.
Baldwin herself has a long history with the organization. She joined as an accountant in 2014, later served as interim director, and was named Chief Executive Officer in early 2022, Oswego County Business Magazine has reported. Her tenure has coincided with the YMCA's push to expand well beyond traditional programming.
The Oswego YMCA supports community programs and family services, including scholarships.
For festivalgoers filing through Washington Square Park this weekend, the connection between pumpkin-shaped fun and the YMCA's wider social safety net may not be obvious. But each ticketless visit to the bounce houses, craft stalls and bandstand helps keep that 170-year-old institution funded for another year of scholarships, camps and community programs across Oswego County.
