Jim Moore / June 2, 2026
Penn Yan NY – Downtown Penn Yan will once again be filled with classic vehicles, live entertainment, and family-friendly activities when Cruisin’ Night & Block Party returns on Friday, June 5. Hosted by the Downtown Business Council of Penn Yan, the event will take place from 4 to 8 p.m. along Main Street and is expected to feature as many as 200 vintage vehicles on display. Organizers describe the annual gathering as one of the community’s signature summer events, bringing together car enthusiasts, residents, visitors, local businesses, and community organizations.
In addition to the vehicle showcase, attendees can enjoy live music from Decades Band and Madelyn Rose. The event will also include a free children’s activity area hosted by Mozaic, featuring cotton candy, popcorn, crafts, face painting, balloon art, and other activities. Multiple food vendors are scheduled to participate, offering a variety of food and beverage options throughout the evening. Admission to the event is free.
Cruisin’ Night is part of Penn Yan’s First Friday activities and is intended to highlight the village’s downtown district. Visitors will have access to numerous restaurants, shops, and businesses located throughout the downtown area during the event. The Downtown Business Council assumed responsibility for organizing Cruisin’ Night in 2025, continuing a tradition that has long brought classic cars, live entertainment, and community engagement to Main Street.
