Sudlersville Peach Festival
Aug. 1, 10 a.m.-3 p.m. | Sudlersville
This annual festival at Godfrey’s Farm features local peaches and peach-based foods for sale, as well as live music, a craft fair and activities for kids.
Free | godfreysfarm.com
Rock Hall Pirates and Wenches Weekend
Aug. 7-9, 5-11 p.m. Friday, 9 a.m.-11 p.m. Saturday, 10 a.m.-3 p.m. Sunday | Rock Hall
Dress up and talk like a pirate at this annual weekend of fun with a costume contest, historical reenactments, mermaids and more!
Free | rockhallpirates.com
National Watermelon Day at the Benson-Hammond House
Aug. 8, 11 a.m.-3 p.m. | Linthicum
The Ann Arrundell County Historical Society presents fresh watermelon and bluegrass music at the Benson-Hammond House in celebration of National Watermelon Day.
Free | aachs.org
‘What Team?!’ – High School Musical 20th Celebration
Aug. 8, 2-3 p.m. | Annapolis
Fans young and old can celebrate the 20th anniversary of the Disney Channel musical classic at Discoveries: The Library at the Mall. Costumes are encouraged!
Free | aacpl.net
North Beach Volunteer Fire Department Centennial Parade and Muster
Aug. 8, 3-8 p.m. | Chesapeake Beach
The North Beach Volunteer Fire Department is celebrating its 100th anniversary with a parade of modern and vintage fire trucks along the North Beach boardwalk, with additional activities at the fire station following the parade.
Free | northbeachfire.com
Legacy Day 2026
Aug. 14-16, 7 p.m. Friday, 9:30 a.m. Saturday, 1 p.m. Sunday | Chestertown
Learn about the rich history and culture of African American communities in Kent County at this annual event at Sumner Hall. This year’s focus is historic communities.
Free | sumnerhall.org/programs/legacy-day
Historic Annapolis Presents – Women’s Equality Day: Remember the Ladies
Aug. 22, 11 a.m.-3 p.m. | Annapolis
The Hogshead Trade Museum is celebrating Women’s Equality Day by highlighting the contributions of women during the Revolutionary War. Living historians will discuss what their lives were like at the time.
Free (donations suggested) | annapolis.org/event
159th Annual Jousting Tournament and Bazaar
Aug. 29, 10 a.m. | Port Republic
Experience Maryland’s official state sport at this long-running event at Christ Church where you can cheer on your favorite riders and horses, as well as enjoy live music and shopping at a medieval-themed bazaar.
Free | christchurchcalvert.org
