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
Annapolis Fall Italian Festa 2026 Sun, 20 Sep at 10:00 am 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 NONPROFIT
Annapolis First Sunday Arts Festival Sun, 03 May Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 FESTIVALS
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
Maryland Renaissance Festival - Photo Meetup 2026 Sat, 26 Sep at 11:00 am Maryland Renaissance Festival USD 4 TO 29 FESTIVALS
Party in the Port 2026 Sat, 17 Oct at 06:00 pm 317 First St, Annapolis, MD, United States, Maryland 21403 MUSIC
Annapolis Murder Mystery: Solve the case! Thu, 01 Oct at 12:00 am 101 State Cir, Annapolis, MD 21401, USA USD 10 TRIPS-ADVENTURES
WED 10/7/26: Marvel Midnight Universe – Midnight Launch Party Wed, 07 Oct at 12:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401
Crushed Glass Craft @NEO PIZZA Annapolis w/MARYLAND CRAFT PARTIES Tue, 22 Sep at 06:00 pm Neo Pizza Annapolis USD 50 TO 64 FITNESS
Walt Wilkins and Marc Douglas Berardo in Annapolis Wed, 23 Sep at 08:00 pm 49 West Coffeehouse, Gallery and Winebar USD 23 FITNESS
The Sound of Liberty: Celebrating America 250 Sun, 20 Sep at 04:00 pm St Margarets Episcopal Church USD 0 TO 25 FITNESS
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
🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷 Wed, 23 Sep at 06:30 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401 MUSIC
AND Creative Film Club (September) - "a Ghost Story" (2017 by David Lowery) Fri, 25 Sep at 06:00 pm AND Creative Studio USD 18 ENTERTAINMENT
Friday Night Kids Club: Pizza, Art, Games & Movies (Ages 6-10) Fri, 25 Sep at 05:30 pm 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 KIDS
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
PlanetTyrus Tour Jan. 24th Annapolis, MD Sun, 24 Jan at 07:30 pm DoubleTree by Hilton Hotel Annapolis USD 28 TO 315 FITNESS
Jessica Kirson at Maryland Hall for the Creative Arts Thu, 28 Jan at 08:00 pm Maryland Hall for the Creative Arts ART
MUTLU with Special Guest, Noah Pierre in Annapolis, MD Mon, 21 Sep at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23 FITNESS
Frequency: The Secret of Everything screening and Q&A in Annapolis, MD Tue, 22 Sep at 06:15 pm Landmark Theater at Annapolis Harbour Center USD 25 FITNESS
The Good Times Experience Sat, 14 Nov at 08:00 pm Metropolitan Kitchen & Lounge USD 18 TO 29 TRIPS-ADVENTURES
Feast on the Farm: A Celebration of Conservation Sat, 24 Oct at 03:00 pm Mas Que Farm USD 215 TO 269 MUSIC
T Rose Bridal Show Annapolis 2026 Sun, 06 Dec at 12:00 pm Crowne Plaza Annapolis by IHG USD 18 EXHIBITIONS
Fiesta de Halloween. Sat, 24 Oct at 12:00 am The Church of Jesus Christ of Latter-day Saints FREE FITNESS
Amelia White and Meg Murray in Annapolis Mon, 15 Mar at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23 FITNESS
Make Maryland ADD Again MATH PARTY USA participate Create your own events Sat, 16 Jan at 09:00 am Sandy Point State Park FREE FITNESS