A beautifully restored vintage runabout is showcased along the Kent Narrows waterfront during the Chesapeake Bay Motoring Festival, which celebrates classic cars and antique boats in a relaxed Eastern Shore setting. Get advanced discounted tickets at www.chesapeakebaymotoringfestival.org. Photo by Ken Visser
Family-friendly two-day event returns June 6–7 to Kent Island Yacht Club with vintage vehicles, waterfront views, and youth activities
The roar of vintage engines, gleaming classic boats, and the thrill of Formula 1 racing will converge on Maryland’s Eastern Shore as the 10th annual Chesapeake Bay Motoring Festival returns June 6–7, 2026, to the waterfront lawns of the Kent Island Yacht Club.
Hosted by the Kent Island Yacht Club and presented by Bentley Washington DC, the two-day celebration features antique and classic automobiles, hot rods, sports cars, motorcycles, tractors, and antique and classic boats, while motorsports fans can watch the Monaco Grand Prix festivities live throughout the weekend. Galahad Marine and the Chesapeake Bay Chapter of the Antique & Classic Boat Society are sponsoring the event.
Set against the scenic Kent Narrows waterfront, the festival blends automotive and maritime heritage with a relaxed summer atmosphere. Enthusiasts and casual guests alike can stroll the show field, enjoy waterfront dining, and meet collectors from across the Mid-Atlantic.
This year, the festival will honor the incredible contributions of first responders, veterans, watermen, and our brave fire and police teams. The day will be filled with opportunities to show your appreciation, enjoy community spirit, and hear inspiring stories.
“We are grateful for the opportunity to host the Chesapeake Bay Motoring Festival at the Kent Island Yacht Club,” said KIYC Commodore Julie Orsini. “It’s a wonderful way to kick off the summer with cool cars and beautiful boats in a relaxed waterfront setting. Guests can enjoy great food, sweet treats, and a friendly gathering of enthusiasts while taking in the views of the Kent Narrows Waterway.”
A Weekend for All Types of Machines
Participants may enter vehicles or boats for one or both days, and entrants do not need to show both days to be eligible for awards.
The weekend opens Saturday with a lively Cars & Coffee-style gathering welcoming everything from vintage classics and muscle cars to motorcycles and antique tractors.
Sunday concludes with the festival’s popular drive-up awards ceremony, featuring the same lighthearted and unusual award categories that have become a fan favorite.
Racing Takes Center Stage
The festival takes place during Monaco Grand Prix weekend, giving visitors the chance to watch one of the world’s most famous races while enjoying the show.
Televisions in the Kent Island Yacht Club bar will broadcast the race, and a large-screen viewing will take place during the club’s Sunday Champagne Brunch beginning at 9 a.m.
Family-Friendly Fun
Organizers have made this year’s festival especially welcoming for families, with free and discounted admission and youth activities.
Discounted advance online tickets are $20 each and good for both days, providing guests access to the yacht club the entire weekend, with youth ages 15 and under admitted free. Otherwise, admission is $25 good for both days after May 27th.
Young guests can participate in a spirited Pinewood Derby Grand Prix race, with a special award each day for the winner. Youth and scout groups may bring their own Pinewood Derby racecars or decorate and personalize one provided at the festival before joining the race.
Waterfront Setting
Guests can also enjoy live entertainment, local food vendors, craft beverages, and waterfront views throughout the weekend.
Visitors arriving by boat may inquire about dockage at the Kent Island Yacht Club, though space is limited.
Entrant applications for cars, motorcycles, tractors, and boats, along with advance tickets and more information, are available at www.chesapeakebaymotoringfestival.org.
About the Chesapeake Bay Motoring Festival
Held annually at the Kent Island Yacht Club, the Chesapeake Bay Motoring Festival is a two-day celebration of automotive and maritime heritage featuring classic cars, motorcycles, tractors, and antique boats. The family-friendly event combines motoring culture with the scenic charm of Maryland’s Eastern Shore.