23 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Naptown Flea Night Market Fri 7 Aug 2026, 5:00 PM — Market Naptown Flea (114 West St) · 114 West St, Annapolis, MD 21401 · Free
Laughs in the Lounge Fri 7 Aug 2026, 7:00 PM — Comedy Stan & Joe's Saloon · 37 West St, Annapolis, MD 21401 · $23.18 · 21+
Pure Comedy: Annapolis Stand Up Showcase Fri 7 Aug 2026, 8:00 PM — Comedy Pure Boardshop · 1908 Forest Dr, Annapolis, MD 21401 · $17.85 · 18+
Group Past Life Regression and Sound Bowls Sun 9 Aug 2026, 10:30 AM — Meetup Annapolis Crystals · 6 Fleet St, Annapolis, MD 21401 · $55.20 · 18+
Meet, Mix & Mingle with Singles 30-49 Wed 12 Aug 2026, 6:30 PM — Meetup DRY 85 · 193 Main St, Annapolis, MD 21401 · $9.31 · 21+
Anne Arundel County Multicultural Center Community Workshop Thu 13 Aug 2026, 6:00 PM — Meetup Michael E. Busch Annapolis Library · 1410 West St, Annapolis, MD 21401 · Free
Folklore & Folktales - Opening Reception and Night Market Sat 15 Aug 2026, 6:00 PM — Art show AND Creative Studio · 1851 McGuckian St, Annapolis, MD 21401 · Free
Pierce Pettis with Danielle Howle Mon 17 Aug 2026, 7:30 PM — Live music 49 West Coffeehouse, Winebar & Gallery · 49 West St, Annapolis, MD 21401 · $23.18
The West Philadelphia Billionaire Society - Book Lecture & Signing Wed 19 Aug 2026, 6:00 PM — Meetup Michael E. Busch Annapolis Library · 1410 West St, Annapolis, MD 21401 · Free
Women in Business Networking Annapolis Fri 21 Aug 2026, 8:00 AM — Meetup Annapolis Crystals · 6 Fleet St, Annapolis, MD 21401 · Free
Maryland Makers Market - Annapolis Fri 21 Aug 2026, 10:00 AM — Market Truxtun Park · 273 Hilltop Ln, Annapolis, MD 21403 · Free
Open Stitch Night Tue 25 Aug 2026, 6:00 PM — Crafts Timber Pizza Co. Annapolis · 192 West St, Annapolis, MD 21401 · $49.87 · 18+
AND Creative Film Club - Kim Merced Garland Retrospective Fri 28 Aug 2026, 6:00 PM — Live show AND Creative Studio · 1851 McGuckian St, Annapolis, MD 21401 · $17.85 · 18+
Old Head: Live on the Red Stage Sat 29 Aug 2026, 4:20 PM — Live music ArtFarm · 111 Chinquapin Round Rd, Annapolis, MD 21401 · $23.18
Mediumship Experience and Dinner with Medium Debbie Mon 14 Sep 2026, 5:30 PM — Meetup Luna Blu Ristorante Italiano · 36 West St, Annapolis, MD 21401 · $103.22 · 18+
Ballet in the Garden at the Hammond-Harwood House Sat 19 Sep 2026, 5:00 PM — Theater Hammond-Harwood House · 19 Maryland Ave, Annapolis, MD 21401 · $64.46
Viva la Musica! A Night of Fire & Flair Sat 19 Sep 2026, 7:30 PM — Live music Maryland Hall · 801 Chase St, Annapolis, MD 21401 · Free
MUTLU in Annapolis Mon 21 Sep 2026, 7:30 PM — Live music 49 West Coffeehouse, Winebar & Gallery · 49 West St, Annapolis, MD 21401 · $23.18
Walt Wilkins and Marc Douglas Berardo Wed 23 Sep 2026, 8:00 PM — Live music 49 West Coffeehouse, Winebar & Gallery · 49 West St, Annapolis, MD 21401 · $23.18
Tarot 101 at Annapolis Crystals Sat 10 Oct 2026, 10:00 AM — Meetup Annapolis Crystals · 6 Fleet St, Annapolis, MD 21401 · $23.18 · 18+
Mini Performance of La Sylphide - Ballet Theatre of Maryland Fri 16 Oct 2026, 10:30 AM — Theater Maryland Hall · 801 Chase St, Annapolis, MD 21401 · $11.66
Metropolitan Cigar & Whiskey Night Tue 20 Oct 2026, 7:00 PM — Meetup Metropolitan Kitchen & Lounge · 175 West St, Annapolis, MD 21401 · $50 · 21+
Halloween Spooktacular at St. John's College Sun 25 Oct 2026, 3:00 PM — Spooky St. John's College · 60 College Ave, Annapolis, MD 21401 · Free
Listings are seeded from venue and organiser calendars. See them on the map.