Jamestown,NY
Classic Cars, Family Fun, People’s Choice Voting, and Support for Aspire of WNY.
The streets of downtown Jamestown will once again come alive with the sights and sounds of classic automobiles as the 33rd Annual Jamestown Cruise-In returns on Friday, August 14, 2026, from 5-9pm.
Hosted by My Chautauqua and Wicked Warren’s, Cruise-In has become one of the region’s premier automotive events, attracting hundreds of classic cars, hot rods, muscle cars, trucks, and custom vehicles while drawing thousands of spectators from across Western New York and Northwestern Pennsylvania.
Admission is free for spectators, making it a perfect summer evening for families, car enthusiasts, and anyone who appreciates beautiful automobiles and a vibrant downtown atmosphere.
Visitors can enjoy an incredible lineup of classic vehicles, live music from the event DJ, local food vendors, and interactive activities throughout the evening.
Supporting Aspire of WNY Cruise-In 2026 is proud to announce Aspire of WNY as this year’s charity recipient.
Aspire of WNY has served individuals with developmental disabilities and behavioral health needs for decades, providing programs and services that empower people to live more independent and fulfilling lives.
During the event, a 50/50 Raffle will be held with half of the proceeds awarded to one lucky winner, while the remaining half will be divided among the top three finishers in the People’s Choice competition, giving participating car owners an opportunity to compete for cash prizes while supporting a great local cause.
People’s Choice Voting Goes Digital
Spectators will once again decide which vehicles take home the coveted People’s Choice Awards
using their smartphones. Each registered vehicle will display a windshield card featuring a unique QRcode, allowing visitors to simply scan the code and vote for their favorite ride.
Vehicle Registration
Owners of classic cars, hot rods, muscle cars, trucks, and specialty vehicles are encouraged to register early. Registration Opens begins at 3pm at Spring & 3rd Streets, Downtown Jamestown and is $15, cash only.