Annapolis Events May 2027
Concerts, sports, comedy shows, Broadway performances, and live events across Annapolis, MD.
- Updated: November 13, 2026
Explore upcoming events in Annapolis in May 2027, including concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment across the city and nearby areas. Browse events by date, venue, category, and neighborhood throughout the month.
- 13 Upcoming Events
- 7 Event Categories
Browse Events in May By Category
- All Events 13
- broadway 13
- Live Shows 13
Popular Events in May
Annapolis Events by Date
Browse events happening each day during May 2027.Annapolis Events Schedule – May 2027
Browse concerts, sports, comedy shows, Broadway performances, festivals, and live events across Annapolis.- May 01, 2027, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats,
1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 32. Select Seats - May 01, 2027, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 02, 2027, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $127, Tickets Available: 30. Select Seats
- May 06, 2027, 7:30 PM Thu — MUSICAL / PLAY: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 07, 2027, 8:00 PM Fri — MUSICAL / PLAY: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 08, 2027, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 08, 2027, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 09, 2027, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $127, Tickets Available: 30. Select Seats
- May 13, 2027, 7:30 PM Thu — MUSICAL / PLAY: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 14, 2027, 8:00 PM Fri — MUSICAL / PLAY: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 15, 2027, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 15, 2027, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
- May 16, 2027, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Dames At Sea at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats
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About Events in Annapolis During May 2027
May 2027 features concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment across Annapolis and nearby MD areas. Major arenas, theaters, clubs, and entertainment venues continue to update their schedules throughout the month.
Browse All Events in May
Frequently Asked Questions
What events are happening in Annapolis during May 2027?
Annapolis hosts concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment throughout May 2027.
Where can I find Annapolis events by date?
Use the monthly event calendar and date filters to browse concerts, sports events, comedy shows, and live performances happening across Annapolis.
Are concerts happening in Annapolis during May 2027?
Yes. Concert schedules include touring artists, arena shows, local performances, music festivals, and live entertainment events throughout Annapolis and nearby MD areas.
What are the top event venues in Annapolis?
Popular venues include arenas, theaters, comedy clubs, stadiums, music halls, and entertainment venues located across Annapolis and nearby areas.
Do event prices change during May 2027?
Yes. Event prices can change based on demand, seating location, performer popularity, venue size, and event date.
Are there weekend events in Annapolis?
Yes. Weekends are usually the busiest time for concerts, sports games, comedy shows, festivals, and major live entertainment events across Annapolis.