Events in Annapolis Find Events in Annapolis Filter Results: October (335) November (678) December (510) (-) January (131) February (95) March (66) April (38) May (22) June (19) July (9) August (10) September (4) Cities Annapolis (197) Regions Central Maryland (197) Types Fairs & Festivals (1) Food & Drink (9) History & Heritage (51) Literary Arts (10) Miscellaneous (11) Multicultural (3) Nature & Outdoor (50) Ongoing (45) Performing Arts (139) Sports (2) Visual Arts (16) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters October 31-December 28, 2025 Colonial Annapolis Walking Tour (+ USNA option) Annapolis Learn More October 31-December 27, 2025 Maryland State House Tour Annapolis Learn More October 31-November 15, 2025 Dracula: A Comedy of Terrors Annapolis Learn More November 1-December 6, 2025 Scandalous Annapolis Annapolis Learn More November 1-2, 2025 Crack The Sky Annapolis Learn More November 1-9, 2025 Children's Theatre of Annapolis presents WEST SIDE STORY Annapolis Learn More November 1-December 28, 2025 Colonial Annapolis Walking Tour (+ USNA option) Annapolis Learn More November 1-December 27, 2025 Maryland State House Tour Annapolis Learn More November 1-15, 2025 Dracula: A Comedy of Terrors Annapolis Learn More November 1-22, 2025 Kinder Theater Annapolis Learn More November 2, 2025 First Sunday Arts Festival Annapolis Learn More November 2, 2025 Crack The Sky Annapolis Learn More Pagination First Previous Page 1 Page 2 Page 3 Current page 4 Page 5 Page 6 Page 7 Page 8 Page 9 … Next Last