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.

72nd Annual Wachapreague Volunteer Firemen’s Carnival

Bloxom Fireman’s Music Festival

Featuring Drew Green with special guests Kylie Morgan, MAURICE, Audio Hum & Dee Ervin

Adult Beverages and Food Included

$10,000 In Cash and Prizes 

Doors open at 3:30 p.m. Show starts at 4:00 pm

For ticket information log onto the Bloxom Fire Company Fund Raising Facebook Page

Play All Day VA

Passport to Northampton County returns Saturday, June 20, with a full day of free family-friendly activities across Northampton County. Participants can visit parks, beaches, recreation facilities, festivals, and community events while collecting stamps in a Passport Book for a chance to win prizes. Activities include kayaking, beach yoga, mini golf, fitness classes, open gym, flag football, pickleball, a community cookout, live music, and more. The day concludes with family activities and prize drawings at Randy Custis Memorial Park in Nassawadox, along with fireworks over the bay at SailFest in Cape Charles. The event celebrates health, wellness, recreation, and community connections throughout Northampton County.

 Greater Works Worship Center Yard Sale

Accomack NAACP Juneteenth Celebration

Northampton NAACP Juneteenth Celebration

Adams UMC Family Prom

Saturday June 20 from 3-10 pm at Adams UMC Parksley

Boys and Girls Club Summer Program

Wachapreague Cure for Coats’ 5k

Wachapreague Cure for Coats’ 5k is a community fundraising event to support research to find a cure for early childhood blindness. Coats’ Disease affects 1 in 300,000 children. Every donation goes directly to the Coats’ foundation and automatically enters you in the raffle for amazing prizes donated from local merchants and artists. The donation link will take you to the Oliver Family page. We are supporting Harlan Oliver’s fight for a cure.

You can walk, run, bike, or golf cart all or part of the distance. You can donate early or show up the day of the event and register with a cash donation. (Internet is spotty in the park.)

Sunday, June 21, 8 am Powell Park in Wachapreague.