Week of 5/14-5/20
Thursday, May 14
42nd Street | Classic Theatre of Maryland (May 14-17)
Friday, May 15
Ballet Storytime & Preview | Eastport-Annapolis Neck Library
Saturday, May 16
Infinite Hero Presents 22 Miles to Break Boundaries | Annapolis High School (May 16-17)
Flea Market & Craft Sale | Anne Arundel County Fairgrounds
Historic Annapolis Presents Mr. Paca’s Garden Storytime: Mommy Time | William Paca House & Garden (May 16 & 19)
Spring Craft Fair | Earleigh Heights Fire Department
Kent Island Heritage Society Presents Kent Island Day | 408 Love Point Road, Stevensville
Gaithersburg Book Festival | Bohrer Park
Chesapeake Catfish Cook-Off | Annapolis Maritime Museum: Park Campus
Armed Forces Day Concert | United States Naval Academy: Radford Terrace
Put it in the Pock3t | Maryland Hall
The Blue Ribbon Bash | Severna Park Elks Lodge
A Musical Melting Pot | Live Arts Studio
The Erin Levitas Foundation Presents a Stroll & Roll | Camden Yards Sports Complex
The Lone Bellow | Rams Head On Stage
Sunday, May 17
Makers of Maryland Presents the Anchors & Artisans Pop-Up Market | Annapolis Town Center
Burgers & Bands for Suicide Prevention | Severna Park Taphouse
Taste of Spring on West Street | 53 West Street, Annapolis
The Talent Machine Company Presents a Cash Bingo Bonanza | Glen Burnie Elks Lodge
Annapolis Symphony Academy Day | Maryland Hall
Monday, May 18
Emerald Society Golf Tournament | Walden Country Club
Wednesday, May 20
Blue Angels Paddle | Capital SUP Eastport
Blue Angels Show | Annapolis
Dinner Under the Stars | 53 West Street, Annapolis
Chantal Kreviazuk | Rams Head On Stage






Annapolis Moms Deal Drop | May 12, 2026