CNY Pumpkin Festival Returns To Oswego For A Weekend Of Fall Fun

OSWEGO – The CNY Pumpkin Festival returns to Oswego’s Washington Square Park on Saturday, October 3 and Sunday, October 4, 2026, from 11am to 6pm Saturday and 11am to 5pm Sunday. This free, family-focused fall festival, presented by the Oswego YMCA with additional support from the City of Oswego, Constellation, Spectrum and the Children’s Board of Oswego, will bring a full weekend of live music, entertainment, food and beverages, marketplace vendors, amusements, and activities for all ages.

Festivalgoers can enjoy a variety of attractions throughout the weekend, including bounce houses, pony rides, Ontario Amusements, craft and marketplace vendors, food and beverages, live music, character performances, make-your-own trick-or-treat bags, scarecrow building and more.

The festival opens Saturday at 11am with the marketplace, food and beverage vendors, activities, and family entertainment. The Port-A-Globe Puppet Theater, sponsored by the Children’s Board of Oswego, will present shows at 11:30am, 1pm, 3pm and 4pm, offering free entertainment for children and families.

Live music kicks off Saturday at noon with local favorites Dirtroad Ruckus, performing from 12pm to 2pm. The afternoon continues with Rumi & The Scarlet Witch, who will entertain with performances from 2pm to 3pm, followed by photo opportunities from 3pm to 4pm.

The music continues Saturday afternoon with Frostbit Blue, taking the stage from 3pm to 6pm to keep the festival rocking throughout the afternoon.

Sunday brings another full day of fall fun beginning at 11am. The Port-A-Globe Puppet Theater will once again offer shows at 11:30am, 1pm, 3pm and 4pm. Live music begins at noon with Seth Rasmussen & The Rail Ramblers, performing from 12pm to 2pm.

The afternoon will feature performances by The Sanderson Sisters from 2pm to 3pm, followed by photo opportunities with the trio from 3pm to 4pm. The Jess Novak Band will close out the weekend with live music from 3pm to 5pm.

“We are excited to bring the CNY Pumpkin Festival back to Washington Square Park for another weekend of fall fun,” said Cheryl Baldwin, Executive Director of the Oswego YMCA. “Beyond the fun, this event is an important fundraiser that helps support the YMCA’s vital programs and services for our community throughout the year.”

Event planning is a collaborative effort of Oswego YMCA staff and volunteers, collaborating closely with community partners and supporters to create a fun and welcoming event for residents and visitors.

“We’re pleased to support the CNY Pumpkin Festival and welcome families and visitors to Washington Square Park for a weekend filled with fun, entertainment and community spirit,” said Oswego Mayor Robert A. Corradino. “Events like this are a wonderful way to bring people together and highlight the energy and character of our community. The YMCA, along with its staff, volunteers and community partners, does a tremendous job creating opportunities for families to enjoy Oswego and all that our city has to offer, and we look forward to another great fall weekend in the heart of our community.”

For more information, visit oswegoymca.org or follow the Oswego YMCA on Facebook for event updates and the complete schedule of activities.

CNY PUMPKIN FESTIVAL SCHEDULE OF EVENTS

SATURDAY, OCTOBER 3, 2026
11am–6pm —Festival Opens: Craft, Food & Beverage Vendors, Marketplace, Amusements & Activities
11:30am, 1pm, 3pm & 4pm — Port-A-Globe Puppet Theater Shows
12–2pm — Dirtroad Ruckus — Live Music
2–3pm — Rumi & The Scarlet Witch — Performances
3–4pm — Rumi & The Scarlet Witch — Photo Opportunities
3–6pm — Frostbit Blue — Live Music

SUNDAY, OCTOBER 4, 2026
11am–5pm — Festival Opens: Craft, Food & Beverage Vendors, Marketplace, Amusements & Activities
11:30am, 1pm, 3pm & 4pm — Port-A-Globe Puppet Theater Shows
12–2pm — Seth Rasmussen & The Rail Ramblers — Live Music
2–3pm — The Sanderson Sisters — Performances
3–4pm — The Sanderson Sisters — Photo Opportunities
3–5pm — Jess Novak Band — Live Music

SATURDAY & SUNDAY

Marketplace • Food & Beverages • Bounce Houses • Pony Rides • Ontario Amusements • Activities • Make Your Own Trick-or-Treat Bag • Build a Scarecrow & More!