125 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Walking Tour: Lost History of Frederick (Bailey) Douglass in Old Annapolis Fri 4 Sep 2026, 10:00 AM — class Kunta Kinte-Alex Haley Memorial · 1 Dock Street, Annapolis, MD 21401
PMP Certification Weekend Classroom Training in Annapolis, MD Sat 5 Sep 2026, 9:00 AM — class 1910 Towne Centre Blvd #250 · 1910 Towne Centre Boulevard #250, Annapolis, MD 21401
Ethical Hacking(CEH) Course Weekend Training in Annapolis, MD Sat 5 Sep 2026, 9:00 AM — class 1910 Towne Centre Blvd #250 · 1910 Towne Centre Boulevard #250, Annapolis, MD 21401
Business Analytics Weekend (CBAP) Training in Annapolis, MD Sat 5 Sep 2026, 9:00 AM — class 1910 Towne Centre Blvd · 1910 Towne Centre Boulevard, Annapolis, MD 21401
Lean Six Sigma Green Belt Weekend Classroom Training in Annapolis, MD Sat 5 Sep 2026, 9:00 AM — Comedy 1910 Towne Centre Blvd #250 · 1910 Towne Centre Boulevard #250, Annapolis, MD 21401
CISSP Training Program – Become a Cybersecurity Leader in Annapolis, MD Mon 7 Sep 2026, 9:00 AM — class 1910 Towne Centre Blvd #250 · 1910 Towne Centre Boulevard #250, Annapolis, MD 21401
Data Science with Python Certification Training in Annapolis, MD Tue 8 Sep 2026, 9:00 AM — class 1910 Towne Centre Blvd #250 · 1910 Towne Centre Boulevard #250, Annapolis, MD 21401
Lactation Basics - AAMC Annapolis, MD Wed 9 Sep 2026, 5:00 PM — class 2000 Medical Pkwy · 2000 Medical Parkway, Annapolis, MD 21401
Reflect & Create: A Multidimensional Health Workshop with Alicia & Casey Thu 10 Sep 2026, 6:30 PM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
Fall 2026 Fashion Styling Workshop Series Thu 10 Sep 2026, 6:30 PM — class 2158 Renard Ct · 2158 Renard Court, Annapolis, MD 21401
Pure Comedy: Annapolis Stand Up Showcase Fri 11 Sep 2026, 8:00 PM — Comedy Pure Boardshop · 1908 Forest Drive, Annapolis, MD 21401
Mini Birth Class Sat 12 Sep 2026, 9:00 AM — class AAMC - Clatanoff Pavilion · 2001 Medical Parkway, Annapolis, MD 21401
Past Life Regression and Sound Healing with Terry Levitan Sat 12 Sep 2026, 9:30 AM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
Pure Comedy: Annapolis Stand Up Showcase Sat 12 Sep 2026, 8:00 PM — Comedy Pure Boardshop · 1908 Forest Drive, Annapolis, MD 21401
Sunday Morning Yoga Sun 13 Sep 2026, 7:00 AM — class Ceremony Coffee Roasters - Roastery · 90 Russell Street #500, Annapolis, MD 21401
Naptown Flea x Lucky Girl Market Sun 13 Sep 2026, 10:00 AM — Market Maryland Avenue · Maryland Avenue, Annapolis, MD 21401
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+
September Cabaret 2026 Mon 14 Sep 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
September Cabaret 2026 Tue 15 Sep 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
Chart House Prime- Prisoner Wine Dinner Thu 17 Sep 2026, 7:00 PM — class Chart House Prime · 300 Second Street, Annapolis, MD 21403
Comics for Critters Thu 17 Sep 2026, 7:00 PM — Comedy Harry Browne's Restaurant · 66 State Circle, Annapolis, MD 21401
Laughs in the Lounge Fri 18 Sep 2026, 7:00 PM — Comedy Stan & Joe's Saloon · 37 West Street, Annapolis, MD 21401
You're a Good Man, Charlie Brown Fri 18 Sep 2026, 7:30 PM — Theater Live Arts Maryland Studio · 2002 Annapolis Mall Road, Annapolis, MD 21401
Autumn Light Reiki, Sound Bath & Meditation Sat 19 Sep 2026, 9:30 AM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
THE MUSIC AND CRAFTED CULTURE FEST , ANNAPOLIS. Sat 19 Sep 2026, 10:00 AM — Festival 2747 Riva Rd · 2747 Riva Road, Annapolis, MD 21401
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
The Sound of Liberty: Celebrating America 250 Sun 20 Sep 2026, 4:00 PM — Live music St Margarets Episcopal Church · 1601 Pleasant Plains Road, Annapolis, MD 21409
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
Friendship Builders: A social skills group for children ages 7-8 Tue 22 Sep 2026, 5:45 PM — class Weems Creek Medical Center, Integrated Family Counseling · 600 Ridgely Avenue Ste 213, Annapolis, MD 21401
Crushed Glass Craft @NEO PIZZA Annapolis w/MARYLAND CRAFT PARTIES Tue 22 Sep 2026, 6:00 PM — class Neo Pizza Annapolis · 220 Harker Place Suite 145, Annapolis, MD 21401
"Painting Old Town" a small group, outdoor watercolor experience Wed 23 Sep 2026, 7:00 PM — class State Circle · State Circle, Annapolis, MD 21401
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
The Taste: Celebrate the Chesapeake in Maryland Thu 24 Sep 2026, 6:00 PM — Meetup The Atreeum at Soaring Timbers · 610 North Bestgate Road, Annapolis, MD 21401
Somatic Circle For Highly Sensitive Souls Sat 26 Sep 2026, 10:00 AM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
Gathering of Light: A Soul Guidance Circle with Nancy Shapiro Sun 27 Sep 2026, 12:00 PM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
Great Frogs Wine Tasting to Benefit the Navy SEAL Foundation Sun 27 Sep 2026, 1:00 PM — class Great Frogs Winery · 3218 Harness Creek Road, Annapolis, MD 21403
Sensual Connection for Couples Sun 27 Sep 2026, 4:00 PM — class Restore Studio at Meadow Hill Wellness · 53 Old Solomons Island Road #B, Annapolis, MD 21401
Hamlet Thu 1 Oct 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Fri 2 Oct 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
An Afternoon with Spirit: Evidential Medium Kathy Reese Sat 3 Oct 2026, 1:00 PM — class 6 Fleet St · 6 Fleet Street, Annapolis, MD 21401
Hamlet Sat 3 Oct 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Sat 3 Oct 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Sun 4 Oct 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Thu 8 Oct 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Fri 9 Oct 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Tarot 101 at Annapolis Crystals Sat 10 Oct 2026, 10:00 AM — Meetup Annapolis Crystals · 6 Fleet St, Annapolis, MD 21401 · $23.18 · 18+
Hamlet Sat 10 Oct 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Sat 10 Oct 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Hamlet Sun 11 Oct 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Sex Offender Interview Specialist Course - October 2026 Mon 12 Oct 2026, 8:00 AM — class Westin Annapolis · 100 Westgate Cir, Annapolis, MD 21401
October Cabaret 2026 Mon 12 Oct 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
October Cabaret 2026 Tue 13 Oct 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401 · 21+
Hamlet Thu 15 Oct 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
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
Ballet Theatre of Maryland IN PERSON 2026-2027 Season Subscriptions Fri 16 Oct 2026, 7:30 PM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Hamlet Fri 16 Oct 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Learn Reiki I with Audrey Rai Sat 17 Oct 2026, 9:00 AM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
Hamlet Sat 17 Oct 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
2nd Annual Wellness & Waves Yacht Event 2026 Sat 17 Oct 2026, 5:00 PM — Meetup Annapolis City Dock · Dock Street, Annapolis, MD 21401
Ballet Theatre of Maryland presents "La Sylphide" Sat 17 Oct 2026, 7:00 PM — Theater Maryland Hall · 801 Chase Street, Annapolis, MD 21401
Hamlet Sat 17 Oct 2026, 8:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
Learn Reiki II with Audrey Rai Sun 18 Oct 2026, 9:00 AM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
Hamlet Sun 18 Oct 2026, 2:00 PM — Theater Classic Theatre of Maryland · 1804 West St, Annapolis, MD 21401
ITZALL Goode and SHC Music Tribe Present Pete Best and Dana Cooper Mon 19 Oct 2026, 7:30 PM — Live music 49 West Coffeehouse, Winebar & Gallery · 49 West Street, Annapolis, MD 21401
Metropolitan Cigar & Whiskey Night Tue 20 Oct 2026, 7:00 PM — Meetup Metropolitan Kitchen & Lounge · 175 West St, Annapolis, MD 21401 · $50 · 21+
Fiesta de Halloween. Sat 24 Oct 2026, 12:00 AM — Spooky The Church of Jesus Christ of Latter-day Saints · 1875 Ritchie Highway, Annapolis, MD 21409
Make Imposter Syndrome Your Superpower! Sat 24 Oct 2026, 9:30 AM — class Annapolis Crystals · 6 Fleet Street, Annapolis, MD 21401
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
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
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
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+
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
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
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
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
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
A Christmas Carol Sun 13 Dec 2026, 7:30 PM — Theater Classic Theatre of Maryland · 1804 West St, 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
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
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
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
Listings are seeded from venue and organiser calendars. See them on the map.