Annual Events
The Downtown Business Council of Penn Yan puts on various events within the downtown district throughout the year. Check out a highlight of the exciting events happening in Downtown Penn Yan!
Chicken Wing Walk, first Saturday in March
Tour and taste chicken wings throughout the Downtown Penn Yan at select participating restaurants. Vote for your favorite to be crowned “Best Wings in Penn Yan”. (ticketed event). >> Learn more
Congratulations to the 2026 Winner: Parker’s Grille
Cruisin’ Night & Block Party, Friday, June 5th, 4 p.m. to 8 p.m.
A popular Finger Lakes event for nearly three decades, this early summer tradition brings extra energy and excitement to Main Street. Enjoy hundreds of classic cars, live bands, food, drink, and family-friendly fun. >> More Details
Fall Festival, First Saturday in October (October 3rd, 2026, 11 a.m. to 4 p.m.)
A family-friendly event that includes a horse rides, petting zoo, vendors, live music, food trucks, beer garden, cornhole tournament and more. >> Learn More
Trunk or Treat, Saturday, October 24th, 2026, 4 p.m. to 6 p.m.
A fun children’s event featuring trick or treating right on Main Street, a costume parade, dance party and more! >> Learn More
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