Do Not Miss List

Week of 4/29-5/5

Presented by

Thursday, April 30

Annual May Day Competition | West Annapolis (Apr. 30-May 1)

Hospice of the Chesapeake Presents the Hope After Hours Grief Workshop | Chesapeake Life Center

The Importance of Being Earnest | Annapolis Area Christian School (Apr. 30-May 2)

Friday, May 1

May Day | Downtown Annapolis 

Renegade Monster Trucks | Anne Arundel County Fairgrounds (May 1-3)

Disney’s The Lion King JR. | Children’s Theatre of Annapolis (May 1-17)

Celebrate May Day with Annapolis Moms | Federal House 

Saturday, May 2

Annapolis Book Festival | The Key School 

Spoutwood Farm Presents the May Day Faerie Festival | Rocky Point Park (May 2-3)

Maryland Sheep & Wool Festival | Howard County Fairgrounds (May 2-3)

Children’s Entrepreneur Market | Herald Harbor Volunteer Fire Department

Mother’s Day Small Business Vendor Fair | Sanders Diamond Jewelers 

Sleeping Beauty Ballet | St. John’s College

Navy Baseball vs. Army | United States Naval Academy: Max Bishop Stadium (May 2-3)

Arts Council of Anne Arundel County Presents Paint the Town | United States Naval Academy: Fluegel Alumni Center

Live Arts Maryland Presents Timeless Brilliance | Maryland Hall 

Historic Annapolis Presents the Brewer Hill Cemetery Tour | Brewer Hill Cemetery

Cape St. Claire Garden Club Presents the 2026 Plant Sale | Cape St. Claire Clubhouse

Graham Parker | Rams Head On Stage

Sunday, May 3

Songbird Festival | Maryland Hall 

Vintage Vibe Finds and Artfully Acquired Present the Annapolis Vintage Market | Vintage Vibe Finds 

First Sunday Arts Festival | West Street and Calvert Street, Annapolis 

Spring Fest & Craft Fair | Kent Island Resort 

Annapolis Opera Presents Opera Up-Close | Asbury United Methodist Church 

The Psychology of Serial Killers featuring Dr. Rachel | Rams Head On Stage

Tuesday, May 5

Cinco de Mayo Celebration | Federal House