September 14, 2026

Chesapeake Bay Motoring Festival is June 8-9 in Kent Island

Two rare Duesenbergs on special display

Get your motors running for the 8th annual Chesapeake Bay Motoring Festival, set for Saturday & Sunday, June 8-9, and taking place at the waterfront Kent Island Yacht Club, with music, libations, light fare, vendor tents, and more. The event delivers a spectacular showcase of antique, classic, hot rod, and sports cars alongside a collection of classic boats and yachts, all taking place on the yacht club’s picturesque waterfront lawn.

A highlight of this year’s show will be two rare Duesenberg automobiles on a special exhibition. The ‘his and hers’ automobiles are owned by Jane and Dwight Schaubach of Suffolk, Virginia, and will not be competing for awards. Jane’s 1929 Model J Roadster Duesenberg features black exterior and interior details, with several unique features noted on this car, including an exposed honeycomb radiator, experimental design bumper, simple gas tank cover, hub medallions, and the under-the-hood horn.

Dwight’s 1930 Model J Dual Cowl Phaeton Duesenberg will also be on display and features a tan interior and a red/burgundy exterior. The Model J packed the largest straight-8 ever mounted in an American car, a Lycoming-built 420 CI powerplant with an aluminum twin-cam head, 4 valves per cylinder, and 265 HP—enough to take a Phaeton-bodied prototype to 116 MPH at the Indianapolis Motor Speedway.

The festival kicks off at 8 a.m. on Saturday with a Cars and Coffee meet-up featuring car clubs, hot rods, muscle cars, modern automobiles, and elegant motorcars from bygone days. The car and boat show opens on Saturday and Sunday at 10 a.m., with Saturday’s and Sunday’s entrants eligible to receive show awards. Saturday’s entrants need not shSet featured imageow up on Sunday to receive an award.

On Saturday evening from 4:30 to 6 p.m., entrants and ticket holders are invited to a cocktail party at the yacht club’s waterside tiki bar with live music, and light hors d’oeuvres and drinks available for purchase. The festival concludes on Sunday afternoon with a delightful waterside awards ceremony, featuring unique categories such as “best car to take your momma to church” and “car most inclined to stop for gas.”

The Chesapeake Bay Motoring Festival’s People’s Choice award winner also will be showcased at the St. Michaels Concours d’Elegance on Chesapeake Bay, taking place at the Kent Island Yacht Club on September 27-29, with more at www.smcde.org.

“All types and conditions of cars are welcome to come, entries won’t be competing against either Duesenberg for awards,” said St. Michaels Concours d’Elegance Chair Luke L. Phipps. “Each year just keeps getting better and better with the automobiles and boats that are attracted to this area and festival. We look forward to seeing many familiar faces back at the Yacht Club this year also.”

The Kent Island Yacht Club with support from St. Michaels Concours d’Elegance on Chesapeake Bay produces the annual event, with this year’s presenting sponsors Bentley Motors, Fred Frederick Chrysler Dodge Jeep Ram of Easton, Maryland, and Shore United Bank. Collaborating for the show includes the Chesapeake Bay Chapter of the Antique & Classic Boat Society.

Early sponsors include Preston Automotive Group and Prestige Auto Vault. Vendors at the festival will include Allen Bentley Studio, American Sentry Solar, American Design and Build, Ltd., Car-toons by Booth, and The Winery.

Entrant registration is free and still open, with entrants receiving a complimentary weekend guest pass for access to all of the yacht club’s amenities. Festival attendees are encouraged to arrive by car or boat, with limited dockage available at the Kent Island Yacht Club and Hyatt Place Marina. Advanced marina reservations can be made by contacting info@smcde.org.

The event is open to the public, with early-bird discounted tickets and more information about the Chesapeake Bay Motoring Festival at www.chesapeakebaymotoringfestival.org.

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About Chesapeake Bay Motoring Festival

The Chesapeake Bay Motoring Festival is an annual celebration of classic automobiles, tractors, and boats, held at the Kent Island Yacht Club. The event brings together car enthusiasts and maritime aficionados for a weekend of elegance and motoring excellence.

AI Disclosure: The Spy and its writers may use artificial intelligence tools to support accuracy and clarity in our reporting.

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