SailFest

Cape Charles will welcome four historic sailing vessels and a full weekend of maritime-themed activities, music, history, and family entertainment during SailFest Cape Charles, scheduled for June 19-21, 2026.

The event is part of the statewide Virginia 250 commemoration and recognizes the nation’s 250th anniversary through a celebration of the maritime traditions that helped shape America and Virginia’s Eastern Shore.

Visitors will have the opportunity to tour four featured vessels docked in Cape Charles Harbor, including the schooner A.J. Meerwald, New Jersey’s official tall ship; the Schooner Lynx, a replica of a War of 1812 privateer; the Kalmar Nyckel, a full-scale replica of the vessel that brought Swedish settlers to North America in 1638; and Luna, the Chesapeake Bay’s only working replica of a coastal trading sloop.

In addition to free ship tours, SailFest will feature Revolutionary War reenactors, presentations by local and regional historians, live music, fireworks, sailing demonstrations, children’s activities, artisan vendors, and displays celebrating the Eastern Shore’s rich maritime heritage.

Activities begin Saturday, June 20, with an opening ceremony featuring Alvie Powell performing the National Anthem. Throughout the day, visitors can enjoy touch tanks presented by the Virginia Institute of Marine Science, face painting, petting zoos, knot-tying demonstrations, archaeological exhibits, sailing experiences, and historical presentations. Evening entertainment includes a concert by Three Sheets to the Wind followed by fireworks over Cape Charles Harbor.

Sunday’s schedule includes additional ship tours, educational programs, music performances, sailing activities, and lectures exploring Revolutionary War history, maritime traditions, and the Eastern Shore’s role in the nation’s development. The festival concludes with a performance by Six String Soldiers.

Featured historians and speakers include Dennis Custis, David Scott, M.D., Tyrone Goodwyn, Luke Alexander, retired Admiral Charles Ray, Captain Craig Felker, Jenean Hall, Kentoya Garcia, and Andy Dunton. Topics range from Revolutionary War naval history and Patriots of Color to the origins of the U.S. Coast Guard and the Eastern Shore’s role in America’s first 250 years.

Organizers say the event is designed to provide residents and visitors with a unique opportunity to experience history firsthand while celebrating the maritime traditions that continue to define life along the Chesapeake Bay.

Admission to SailFest Cape Charles is free. Organizers encourage attendees to explore the harbor, tour the ships, enjoy the live entertainment, and experience one of the largest Virginia 250 events planned on the Eastern Shore.

For additional information, schedules, volunteer opportunities, lodging options, and updates, visit SailFestCapeCharles.com.