88 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
The Witching Hour: Mystery & Mirth Fri 30 Oct 2026, 6:30 PM — Comedy 172 Green St · 172 Green Street, Annapolis, MD 21401
Dream Punch, Light Beams, PLRLS, Chain Puller at Metropolitan Fri 30 Oct 2026, 7:00 PM — Live music Metropolitan Kitchen & Lounge · 175 West Street, Annapolis, MD 21401
Le Petit Masquerade @ Rumhouse (Caribbean Fine Dining - Annapolis) Sat 31 Oct 2026, 6:00 PM — Spooky Rumhouse · 422 6th Street, Annapolis, MD 21403
Mike McHenry and his Funkified Clones of Funk Friends Sat 31 Oct 2026, 7:00 PM — Live music Log Rhythm Records Studio · 1801 West Street Suite 100, Annapolis, MD 21401
Annapolis, MD Singles Event: Meet, Mix & Mingle with Singles 30–49 Mon 2 Nov 2026, 6:30 PM — social GameOn bar+arcade · 114 West Street, Annapolis, MD 21401
Lean Six Sigma Green Belt Certification Bootcamp in Annapolis, MD Tue 3 Nov 2026, 9:00 AM — Comedy 1910 Towne Centre Blvd · 1910 Towne Centre Boulevard, Annapolis, MD 21401
Wednesday Wellness: "Tuning Tina" McMahon and Chad Holmes Biofield Tuning Wed 4 Nov 2026, 7:30 PM — Live music Log Rhythm Records · 1801 West Street Suite 100, Annapolis, MD 21401
Chart House Prime - Caymus Wine Dinner Thu 5 Nov 2026, 7:00 PM — class Chart House Prime · 300 Second Street, Annapolis, MD 21403
Newborn Care Sat 7 Nov 2026, 10:30 AM — class Belcher Pavilion · 2000 Medical Parkway, Annapolis, MD 21401
A Soft Return Sun 8 Nov 2026, 11:00 AM — Fitness 1701 Belle Dr · 1701 Belle Drive, Annapolis, MD 21401
Come Out and Play in DMV/Annapolis 2026 Fri 13 Nov 2026, 7:00 PM — Theater 210 Holiday Ct · 210 Holiday Court, Annapolis, MD 21401
Triple Threat: A night of Rock and Metal! Fri 13 Nov 2026, 8:00 PM — Live music Log Rhythm Records · 1801 West Street Suite 100, Annapolis, MD 21401
Laughs in the Lounge Sat 14 Nov 2026, 7:00 PM — Comedy Stan & Joe's Saloon · 37 West Street, Annapolis, MD 21401
The Good Times Experience Sat 14 Nov 2026, 8:00 PM — Live music Metropolitan Kitchen & Lounge · 175 West Street, Annapolis, MD 21401
November Cabaret 2026 Mon 16 Nov 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
Ari Hest at 49 West in Annapolis, MD Mon 16 Nov 2026, 7:30 PM — Live music 49 West Coffeehouse, Winebar & Gallery · 49 West Street, Annapolis, MD 21401
November Cabaret 2026 Tue 17 Nov 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
An Invitation To An Evening For A Taste Of Frequency And Flow Thu 19 Nov 2026, 7:30 PM — Live music Log Rhythm Records Studio · 1801 West Street Suite 100, Annapolis, MD 21401
Wellness Market Sat 21 Nov 2026, 10:00 AM — Market The Collective · 2158 Renard Court, Annapolis, MD 21401
Holiday Inn Fri 27 Nov 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sat 28 Nov 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sat 28 Nov 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sun 29 Nov 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Lean Six Sigma Green Belt Certification Bootcamp in Annapolis, MD Tue 1 Dec 2026, 9:00 AM — Comedy 1910 Towne Centre Blvd · 1910 Towne Centre Boulevard, Annapolis, MD 21401
Wednesday Wellness: "Tuning Tina" McMahon and Chad Holmes Biofield Tuning Wed 2 Dec 2026, 7:30 PM — Live music Log Rhythm Records · 1801 West Street Suite 100, Annapolis, MD 21401
A Christmas Carol Thu 3 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Fri 4 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sat 5 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
2026 FRA 24 Holiday Party Sat 5 Dec 2026, 6:00 PM — Live music Fleet Reserve Club Of Annapolis · 100 Compromise Street, Annapolis, MD 21401
A Christmas Carol Sat 5 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
T Rose Bridal Show Annapolis 2026 Sun 6 Dec 2026, 12:00 PM — Meetup Crowne Plaza Annapolis by IHG · 173 Jennifer Road, Annapolis, MD 21401
Holiday Inn Sun 6 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Encore Chorale Annapolis Concert Sun 6 Dec 2026, 4:00 PM — Live music Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Encore ROCKS Annapolis Concert Sun 6 Dec 2026, 7:00 PM — Live music Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Holiday Inn Sun 6 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Mini Performance of The Nutcracker by Ballet Theatre of Maryland Wed 9 Dec 2026, 9:30 AM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Holiday Inn Wed 9 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Thu 10 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Fri 11 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Breakfast with Santa at Historic Inns of Annapolis Sat 12 Dec 2026, 10:00 AM — Live music The Governor Calvert House at Historic Inns of Annapolis · 58 State Circle, Annapolis, MD 21401
Ballet Theatre of Maryland presents "The Nutcracker" Sat 12 Dec 2026, 1:00 PM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
A Christmas Carol Sat 12 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Ballet Theatre of Maryland presents "The Nutcracker" Sat 12 Dec 2026, 7:00 PM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Holiday Inn Sat 12 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sun 13 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Voices of the Season Sun 13 Dec 2026, 7:00 PM — Live music Eastport United Methodist Church · 926 Bay Ridge Avenue, Annapolis, MD 21403
A Christmas Carol Sun 13 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Breastfeeding Support Group in-person Mon 14 Dec 2026, 10:00 AM — Support group AAMC Clatanoff Pavilion · Rotary Room 2001 Medical Parkway, Annapolis, MD 21401
December Cabaret 2026 Mon 14 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
December Cabaret 2026 Tue 15 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
Holiday Inn Wed 16 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Thu 17 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Fri 18 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Sat 19 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Ballet Theatre of Maryland presents "The Nutcracker" Sat 19 Dec 2026, 7:00 PM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Handel's Messiah Sat 19 Dec 2026, 7:30 PM — Live music St. Anne's Parish · 199 Duke of Gloucester Street, Annapolis, MD 21401
Holiday Inn Sat 19 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sun 20 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Sun 20 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Mon 21 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Annual Holiday Celebration with the Eric Scott Trio Mon 21 Dec 2026, 7:30 PM — Live music 49 West Coffeehouse, Winebar & Gallery · 49 West Street, Annapolis, MD 21401
Holiday Inn Tue 22 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Wed 23 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Wed 23 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Thu 24 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Thu 24 Dec 2026, 6:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sat 26 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Sat 26 Dec 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
A Christmas Carol Sun 27 Dec 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Sun 27 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Tue 29 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Wed 30 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Holiday Inn Thu 31 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Master Public Speaking & captivate any room with confidence *Online Event* Fri 1 Jan 2027, 6:00 PM — Comedy Annapolis · Annapolis, Annapolis, MD 21401
Lean Six Sigma Green Belt Certification Bootcamp in Annapolis, MD Tue 5 Jan 2027, 9:00 AM — Comedy 1910 Towne Centre Blvd · 1910 Towne Centre Boulevard, Annapolis, MD 21401
Luminis Health Prostate Cancer Support Group Tue 5 Jan 2027, 4:30 PM — Support group Doordan Institute Conference Center and Event Space · 2000 Medical Parkway #7th floor, Annapolis, MD 21401
Wednesday Wellness: "Tuning Tina" McMahon and Chad Holmes Biofield Tuning Wed 6 Jan 2027, 7:30 PM — Live music Log Rhythm Records · 1801 West Street Suite 100, Annapolis, MD 21401
PlanetTyrus Tour Jan. 24th Annapolis, MD Sun 24 Jan 2027, 7:30 PM — Comedy DoubleTree by Hilton Hotel Annapolis · 210 Holiday Court, Annapolis, MD 21401
Ballet Theatre of Maryland presents "Momentum: A Mixed Bill" Sat 20 Feb 2027, 7:00 PM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Echoes of Love & Longing Sun 21 Feb 2027, 3:00 PM — Live music Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Live Arts Maryland presents Music & Film Sat 27 Feb 2027, 7:30 PM — Live music Maryland Hall · 801 Chase Street, Annapolis, MD 21401
It’s Magic! Hits of the Hi-Fi Era Sun 11 Apr 2027, 3:00 PM — Live music Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Mini Performance of Coppélia by Ballet Theatre of Maryland Fri 23 Apr 2027, 10:30 AM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401