Don’t have anything planned for the weekend? Check out these family-friendly events in the Chesapeake, including an outdoor concert and an introduction to kindergarten!
Legacy Day 2026
Aug. 14-16, 7 p.m. Friday; 9:30 a.m. Saturday; 1 p.m. Sunday | Chestertown, MD
Learn about the rich history and culture of African American communities in Kent County at this annual event at Sumner Hall, with this year’s event focused on historic communities.
Free | sumnerhall.org/programs/legacy-day
Kindergarten Kickoff
Aug. 15, 10:30 a.m.-noon | Deale, MD
An event for rising kindergarten students at Deale Library where kids can get ready for school through music, play and stories and learn what to expect in a kindergarten classroom
Free | aacpl.net
Maryland Hall Presents BloomHaven
Aug. 16, 5:30 p.m. | Annapolis, MD
Enjoy live music outdoors at this concert series at the Maryland Hall for the Creative Arts! This weekend’s performers are the Natalie Brooke Band with the Ahmed Warshanna Trio
$17.85, free for children ages 12 and younger | marylandhall.org/bloomhaven
