The Worcester County Chamber of Commerce in Ocean Pines is excited to announce its 12th Annual Classic Car, Truck & Jeep Show on Saturday, August 29, 2026, at the racetrack at Ocean Downs Casino.
This free, family-friendly event will feature classic cars, trucks and Jeeps, local business and nonprofit vendors, food and beverages for purchase, and DJ Rupe, playing legendary music from throughout the decades. Tara Calabrese – Images by Stara will provide onsite photography and drone footage.
The Promenade Sponsor is Bryant Sterling with i.g. Burton Auto Group, and the Entertainment Sponsor is Premier Driving School.
The Chamber thanks the many sponsors who have helped make this annual anchor event possible: 7-Eleven Ocean Pines, BrightStar Care, Chesapeake Bath and Home Solutions, Goosehead Insurance, Gull Creek Senior Living Community, Donna Frankowski/ERA Martin Realty, Embrace Home Loans, Taylor Bank, Carquest Auto Parts & Marine/Ocean Area Tire, OC Tax Service, Preston Automotive Group, Hawkins Electric Service, Nicks Mini Golf, Ryan Murphy with Kastendike Insurance Group, Spicer Bros. Construction, Pushing Paper Bookkeeping, Eastern Shore Property Cleanout, CarePatrol, Your Bayside Concierge and Tide Together Boutique
Event & Registration Information
The car show runs approximately 9:00 a.m. to 12:00 p.m., with trophies awarded at 12:30 p.m. Categories include Classic, Antique, Hot Rod, Modern (2000s+), Custom (Non-Stock), Eurasian, Corvette, Jeep Stock, Jeep Custom, Truck/SUV, Best of Show, People’s Choice, and Honorable Mentions.
Pre-registration is $25 and is available online through Thursday, August 27 at www.WorcesterCountyChamber.org. Onsite registration begins at 8:00 a.m. Saturday, and all vehicles must be registered by 9:00 a.m.
Local businesses and nonprofits are invited to participate as vendors along the patio. Vendor opportunities are available, and booth space is free for nonprofits.
For car show registration or vendor information, call the Chamber at 410-641-5306 or visit the Worcester County Chamber Visitor Center, 11047 Racetrack Road, Berlin, MD 21811, located behind the ERA Realty office.
For additional information, contact 410-641-5306 or info@WorcesterCountyChamber.org.
