Children’s Day on the Farm
June 7, 11 a.m.-4 p.m. | St. Leonard
A children’s event at Jefferson Patterson Park and Museum about rural life in the past and present, featuring educational exhibits, live entertainment, wagon rides and more!
Free | jefpat.maryland.gov
Third Annual Summer Fest
June 13, 10 a.m.-3 p.m. | Linthicum
The Benson-Hammond House is holding its third annual summer celebration, featuring live music, entertainment and a vendor fair. Schedule a guided tour of the historic house for $5.
Free | aachs.org
Maryland Crafted: Centreville
June 13, Noon-5 p.m. | Centreville
Artists, vendors, restaurateurs and more gather at Centreville Town Hall for an afternoon of live entertainment, art and other activities at this event typically drawing in thousands of visitors and locals.
Free | townofcentreville.org
Arts Annapolis 2026
June 13, Noon-10 p.m. | Annapolis
Arts Annapolis is meant to serve as a test run for an upcoming multi-day art festival scheduled for 2028 and will feature live entertainment from across different performing arts mediums.
Free | acaac.org/event/arts-annapolis-2026
Flag Day at Hogshead Trades Museum
June 14, 11 a.m.-3 p.m. | Annapolis
Join living historians at the Hogshead Trades Museum to learn about the history of the American Flag and the Flag of Maryland. Design your own flags and learn to sew a star!
Free (donations encouraged) | annapolis.org/event/flagday26
Antique Airplane Fly-In 2026
June 20, 10 a.m.-2 p.m. | Massey
Antique planes are landing at the Massey Air Museum during this free event. Families can watch them take flight and get a closer look at these historic aircrafts.
Free | masseyaero.org
Annapolis Juneteenth Festival
June 20, Noon-9 p.m. | Annapolis
Following the 6th Annual Annapolis Juneteenth Parade, a festival celebrating the holiday will be held at Bates Sports Complex, with live music, a vendor fair and a children’s village.
Free | theannapolisjuneteenth.org
