Annual Chesapeake Bay Motoring Festival, a premier celebration of motoring and maritime excellence on Maryland’s Eastern Shore. Taking place on Saturday, June 7th, and Sunday, June 8th, 2025, this unforgettable event will be hosted at the scenic Kent Island Yacht Club in Chester, Maryland.

A Nostalgic Celebration

Join us for a weekend of camaraderie and motoring excellence, where an eclectic display of muscle cars, hot rods, and classic motorcars will meet antique yachts and speed boats to create a truly timeless atmosphere. Against the stunning waterfront backdrop of the Kent Island Yacht Club, this event is the perfect way to enjoy the beauty and history of classic automobiles and boats.

Event Highlights:

- Saturday, June 7th:

- Cars & Coffee: 8:30 AM (for registered entrants and ticket holders)

- Gates Open for Attendees: 10:00 AM

- Displays of Antique Yachts, Classic Boats, and Award-Winning Motorcars 

Throughout the Weekend:

- Antique and Classic Boats: Enjoy stunning watercraft alongside the motorcar displays.

- Regional Fare and Libations: The Kent Island Yacht Club will offer delicious local food and drinks for purchase.

- Notable Automobile Clubs: View exceptional vehicles presented by members of prestigious automobile clubs from the Chesapeake region and beyond.

Schedule of Events

Saturday, June 7th, 2025

- 8:00 AM – 10:00 AM: Cars and Coffee

- A relaxed morning gathering for enthusiasts to enjoy coffee and conversation while admiring classic and exotic cars.

- 8:00 AM – 9:30 AM: Automobiles Take the Field

- Registered vehicles arrive and are arranged for display.

- 10:00 AM – 3:30 PM: Gates Open to Attendees

- Explore the stunning displays of classic cars, antique yachts, and speed boats set against the picturesque waterfront.

- 4:00 PM: Event Concludes for the Day

- 6:00 PM – 7:30 PM: Cocktail Party Welcome Reception

- Join us at the Tiki Bar for an evening of camaraderie, refreshments, and celebration. • One ticket grants access to both days. 

2025 Ticket Options

2025 Early Bird Ticket Price - $25.00

General Admission Ticket Price - $30.00

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