October 2026 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.
Annapolis Events October 2026
Concerts, sports, comedy shows, Broadway performances, and live events across Annapolis, MD.
Explore upcoming events in Annapolis in October 2026, 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.
15
Upcoming Events
7
Event Categories
Popular Events in October
Explore top concerts, sports events, comedy shows, and live performances happening this month.
Annapolis Events by Date
Browse events happening each day during October 2026.Annapolis Events Schedule – October 2026
Browse concerts, sports, comedy shows, Broadway performances, festivals, and live events across Annapolis.Upcoming Confirmed Events 15
- Oct1420268:00 PMWedJAZZ / BLUESGerald AlbrightRams Head On Stage • 300 seatsRams Head On Stage
33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USFrom $85Avg Ticket Price: ~ $120Tickets Available: 144Select Seats - Oct15202610:00 AMThuAnnapolis Sailboat ShowAnnapolis City Dock1 Dock Street, Annapolis, MD 21401, US1 Dock Street, Annapolis, MD 21401, USFrom $64Avg Ticket Price: ~ $7914 tickets remaining!Select Seats
- Oct16202610:00 AMFriAnnapolis Sailboat ShowAnnapolis City Dock1 Dock Street, Annapolis, MD 21401, US1 Dock Street, Annapolis, MD 21401, USFrom $60Avg Ticket Price: ~ $6911 tickets remaining!Select Seats
- Oct17202610:00 AMSatOTHERWeekend EventAnnapolis Sailboat ShowAnnapolis City Dock1 Dock Street, Annapolis, MD 21401, US1 Dock Street, Annapolis, MD 21401, USFrom $59Avg Ticket Price: ~ $6812 tickets remaining!Select Seats
- Oct1720266:00 PMSatJAZZ / BLUESWeekend EventBoney JamesRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USFrom $105Avg Ticket Price: ~ $12313 tickets remaining!Select Seats
- Oct18202610:00 AMSunOTHERWeekend EventAnnapolis Sailboat ShowAnnapolis City Dock1 Dock Street, Annapolis, MD 21401, US1 Dock Street, Annapolis, MD 21401, USFrom $59Avg Ticket Price: ~ $6812 tickets remaining!Select Seats
- Oct1820268:00 PMSunALTERNATIVEWeekend EventFive For FightingRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USAvg Ticket Price: ~ $9134 tickets remaining!Select Seats
- Oct1920268:00 PMMonCOUNTRY / FOLKEvan HonerRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USAvg Ticket Price: ~ $9138 tickets remaining!Select Seats
- Oct2020268:00 PMTueJAZZ / BLUESAcoustic AlchemyRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USFrom $67Avg Ticket Price: ~ $9014 tickets remaining!Select Seats
- Oct2120268:00 PMWedJAZZ / BLUESEddie 9VRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USAvg Ticket Price: ~ $9418 tickets remaining!Select Seats
- Oct2320266:30 PMFriCOUNTRY / FOLKPhil VassarRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USFrom $67Avg Ticket Price: ~ $17716 tickets remaining!Select Seats
- Oct2320269:30 PMFriCOUNTRY / FOLKPhil VassarRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USFrom $67Avg Ticket Price: ~ $16422 tickets remaining!Select Seats
- Oct2420263:30 PMSatCollege (Div I-A and Div I-AA) FOOTBALLHigh DemandWeekend EventNavy Midshipmen vs. North Texas Mean GreenNavy Marine Corps Memorial Stadium • 34000 seatsNavy Marine Corps Memorial Stadium550 Taylor Avenue, Annapolis, MD 21401, US550 Taylor Avenue, Annapolis, MD 21401, USFrom $32Avg Ticket Price: ~ $128Tickets Available: 491Select Seats
- Oct2720268:00 PMTuePOP / ROCKBest ValueMike DawesRams Head On Stage • 300 seatsRams Head On Stage33 West Street, Annapolis, MD 21401, US33 West Street, Annapolis, MD 21401, USFrom $28Avg Ticket Price: ~ $53Tickets Available: 74Select Seats
- Oct2920266:30 PMThuConcertCandlelight: 90s UnpluggedMaryland Hall For The Creative Arts801 Chase Street, Annapolis, MD 21401, US801 Chase Street, Annapolis, MD 21401, USFrom $289Avg Ticket Price: ~ $3332 tickets remaining!Select Seats
Explore Annapolis Events by Month
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October
This Month
Events in October 2026
About Events in Annapolis During October 2026
Browse All Events in October
Browse concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment happening this month.
Gerald Albright
33 West Street, Annapolis, MD 21401
Event Dates 5
Oct 14, 2026 8:00 PM
Annapolis Sailboat Show
1 Dock Street, Annapolis, MD 21401
Event Dates 7
Oct 15, 2026 10:00 AM
Boney James
33 West Street, Annapolis, MD 21401
Event Dates 29
Oct 17, 2026 6:00 PM
Five For Fighting
33 West Street, Annapolis, MD 21401
Event Dates 9
Oct 18, 2026 8:00 PM
Evan Honer
33 West Street, Annapolis, MD 21401
Event Dates 22
Oct 19, 2026 8:00 PM
Acoustic Alchemy
33 West Street, Annapolis, MD 21401
Event Dates 10
Oct 20, 2026 8:00 PM
Eddie 9v
33 West Street, Annapolis, MD 21401
Event Dates 17
Oct 21, 2026 8:00 PM
Phil Vassar
33 West Street, Annapolis, MD 21401
Event Dates 3
Oct 23, 2026 6:30 PM
Navy Midshipmen Football
550 Taylor Avenue, Annapolis, MD 21401
Event Dates 7
Oct 24, 2026 3:30 PM
Mike Dawes
33 West Street, Annapolis, MD 21401
Event Dates 15
Oct 27, 2026 8:00 PM
Candlelight: 90s Unplugged
801 Chase Street, Annapolis, MD 21401
Event Dates 20
Oct 29, 2026 6:30 PM
Frequently Asked Questions
Quick answers about Annapolis events, venues, schedules, and live entertainment.
What events are happening in Annapolis during October 2026?
Annapolis hosts concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment throughout October 2026.
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 October 2026?
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 October 2026?
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.
Event Categories in October
Explore concerts, sports, Broadway shows, comedy events, festivals, and live entertainment across Annapolis.