Maryland Renaissance Festival at Maryland Renaissance Festival Sun, 27 Sep Maryland Renaissance Festival FESTIVALS
BAYGRASS 2026: Annapolis Baygrass Music Festival 9/19-20 Sat, 19 Sep at 10:00 am 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409 MUSIC-FESTIVALS
21st Annual Boatyard Beach Bash Sat, 19 Sep at 04:00 pm 723 2nd St, Annapolis, MD, United States, Maryland 21403 MUSIC
Annapolis Fall Italian Festa 2026 Sun, 20 Sep at 10:00 am 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 NONPROFIT
Peter Mayer Group - Boatyard Beach Bash - Annapolis, MD Sat, 19 Sep at 04:30 pm Annapolis Maritime Museum & Park MUSIC
Annapolis First Sunday Arts Festival Sun, 03 May Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 FESTIVALS
Five for Fighting with String Quartet at Rams Head On Stage Sun, 18 Oct at 08:00 pm Rams Head On Stage TRIPS-ADVENTURES
Southern Culture On the Skids at Rams Head On Stage Sat, 26 Sep at 08:00 pm Rams Head On Stage CALENDAR
Michael Cleveland in Annapolis Sun, 20 Sep at 07:00 pm Annapolis Baygrass Music Festival MUSIC-FESTIVALS
Candlelight: A Haunted Evening of Halloween Classics Thu, 29 Oct at 08:45 pm Maryland Hall USD 31 TO 76 CANDLELIGHT-CONCERTS
Party in the Port 2026 Sat, 17 Oct at 06:00 pm 317 First St, Annapolis, MD, United States, Maryland 21403 MUSIC
The Carole King & James Taylor Story - Tribute Show Sat, 10 Oct at 07:00 pm Rams Head On Stage TRIPS-ADVENTURES
Walt Wilkins and Marc Douglas Berardo in Annapolis Wed, 23 Sep at 08:00 pm 49 West Coffeehouse, Gallery and Winebar USD 23 FITNESS
Rams Head Presents Lalah Hathaway (Annapolis, MD) Mon, 16 Nov at 08:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401 MUSIC
Navy Midshipmen Football vs. Temple Owls Football Sat, 07 Nov at 12:00 am Navy Marine Corps Memorial Stadium SPORTS
2nd Annual Wellness & Waves Yacht Event 2026 Sat, 17 Oct at 05:00 pm Annapolis City Dock USD 189 TO 509 FITNESS
The Sound of Liberty: Celebrating America 250 Sun, 20 Sep at 04:00 pm St Margarets Episcopal Church USD 0 TO 25 FITNESS
Candlelight: 90s Unplugged Thu, 29 Oct at 06:30 pm Maryland Hall For The Creative Arts CANDLELIGHT-CONCERTS
Annapolis Chocolate Binge Festival Sun, 06 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States FESTIVALS
Candlelight: Coldplay & Imagine Dragons Sat, 21 Nov at 06:45 pm Maryland Hall USD 41 TO 87 ENTERTAINMENT
Everyday at QWP thru Sept 30 Water Biiss & Events Annapolis QUIET WATERS PARK Wed, 30 Sep at 10:00 am Quiet Waters Park Annapolis, Md CONCERTS
Ari Hest at 49 West in Annapolis, MD Mon, 16 Nov at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23 FITNESS
Bountiful Harvest - Costumes & Cocktails Fri, 23 Oct at 07:00 pm 10 Hudson St, Annapolis, MD, United States, Maryland 21401 MUSIC
St. John’s Block Party Sat, 24 Oct at 12:00 pm 970 St. John’s Drive, Annapolis, MD 21409 ENTERTAINMENT
Herman's Hermits Starring Peter Noone at Rams Head On Stage Sun, 22 Nov at 04:30 pm Rams Head On Stage CALENDAR
🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷 Wed, 23 Sep at 06:30 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401 MUSIC
North Mississippi Allstars at Rams Head On Stage Thu, 08 Oct at 08:00 pm Rams Head On Stage TRIPS-ADVENTURES
Alan Dale Trio - Multicolored Blue Sun, 27 Sep at 07:00 pm 49 West Coffeehouse, Winebar & Gallery MUSIC
ITZALL Goode and SHC Music Tribe Present Pete Best and Dana Cooper Mon, 19 Oct at 07:30 pm 49 West Coffeehouse, Winebar & Gallery FREE FITNESS
Candlelight: Valentine’s Day Special Sat, 13 Feb at 08:45 pm Maryland Hall USD 31 TO 73 ENTERTAINMENT
Mac Heat @ First Sunday Arts Festival Sun, 04 Oct at 11:00 am West St, Annapolis, MD 21401, United States FESTIVALS
MUTLU with Special Guest, Noah Pierre in Annapolis, MD Mon, 21 Sep at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23 FITNESS
A Night with Reagan Keys, SleepySmile & SIDEQUEST! Live Fri, 25 Sep at 07:30 pm Log Rhythm Records Studio USD 15 FITNESS
Billy Prine presents Songs and Stories of John Prine at Rams Head On Stage Sat, 16 Jan at 01:00 pm Rams Head On Stage
Feast on the Farm: A Celebration of Conservation Sat, 24 Oct at 03:00 pm Mas Que Farm USD 215 TO 269 MUSIC
Candlelight - 90s Unplugged at Maryland Hall for the Creative Arts Thu, 29 Oct Maryland Hall for the Creative Arts ART