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
36th Annual Kunta Kinte Heritage Festival Sat, 26 Sep at 12:00 pm Navy–Marine Corps Memorial Stadium FESTIVALS
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
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
Rams Head Presents Lalah Hathaway (Annapolis, MD) Mon, 16 Nov at 08:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401 MUSIC
Ballet Theatre of Maryland IN PERSON 2026-2027 Season Subscriptions Fri, 16 Oct at 07:30 pm Maryland Hall USD 14 TO 213 FITNESS
The Sound of Liberty: Celebrating America 250 Sun, 20 Sep at 04:00 pm St Margarets Episcopal Church USD 0 TO 25 FITNESS
LGBTQ Paint Night @ NEO PIZZA - Annapolis Wed, 07 Oct at 06:00 pm Neo Pizza & Taphouse USD 55 FITNESS
Annapolis Chocolate Binge Festival Sun, 06 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States FESTIVALS
Ballet Theatre of Maryland presents "La Sylphide" Sun, 18 Oct at 02:00 pm Maryland Hall USD 28 TO 106 FITNESS
Candlelight: Coldplay & Imagine Dragons Sat, 21 Nov at 06:45 pm Maryland Hall USD 41 TO 87 ENTERTAINMENT
"Painting Old Town" a small group, outdoor watercolor experience Wed, 23 Sep at 07:00 pm State Circle USD 35 TO 85 FITNESS
Ballet Theatre of Maryland: The Nutcracker Sat, 12 Dec at 01:00 pm Maryland Hall For The Creative Arts ART
Ari Hest at 49 West in Annapolis, MD Mon, 16 Nov at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23 FITNESS
Sensual Connection for Couples Sun, 27 Sep at 04:00 pm Restore Studio at Meadow Hill Wellness USD 216 TO 290 WORKSHOPS
Mini Performance of La Sylphide by Ballet Theatre of Maryland Fri, 16 Oct at 10:30 am Maryland Hall USD 12 TO 17 FITNESS
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
Meet the Author: Valerie Tripp, An American Girl Doll Author of Meet Felicity, Meet Samantha, & More Sat, 07 Nov at 10:30 am 99 Main Street, Annapolis, MD, United States, Maryland 21401 ART
First Exposure: Beginner Photography (4- week workshop) Mon, 05 Oct at 06:30 pm ArtFarm USD 242 WORKSHOPS
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
"Painting the Town" An Urban Watercolor Painting Experience Wed, 23 Sep at 07:00 pm Fleet St, Annapolis, MD 21401, United States ART
Creative Circle - Monthly Meetup (2026) Thu, 13 Aug 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 ART
Alan Dale Trio - Multicolored Blue Sun, 27 Sep at 07:00 pm 49 West Coffeehouse, Winebar & Gallery MUSIC
WED 9/23/26: Exquisite Corpses Fox Mask Killer #1 launch signing with Che Grayson Wed, 23 Sep at 06:00 pm 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 ART
Candlelight: Valentine’s Day Special Sat, 13 Feb at 08:45 pm Maryland Hall USD 31 TO 73 CANDLELIGHT-CONCERTS
PlanetTyrus Tour Jan. 24th Annapolis, MD Sun, 24 Jan at 07:30 pm DoubleTree by Hilton Hotel Annapolis USD 28 TO 315 FITNESS
Mac Heat @ First Sunday Arts Festival Sun, 04 Oct at 11:00 am West St, Annapolis, MD 21401, United States FESTIVALS
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
Simple Movements for Low Energy Days with Master Trainer Tara De Leon Tue, 20 Oct at 06:30 pm 2158 Renard Ct FREE FITNESS
Candlelight - 90s Unplugged at Maryland Hall for the Creative Arts Thu, 29 Oct Maryland Hall for the Creative Arts ART
Get Closer: Couples Tantra Workshop Sun, 01 Nov at 04:00 pm Restore Studio at Meadow Hill Wellness USD 232 TO 290 WORKSHOPS
PMA at Unplugged at First Sunday Arts Festival Sun, 01 Nov at 02:00 pm First Sunday Arts Festival FESTIVALS
T Rose Bridal Show Annapolis 2026 Sun, 06 Dec at 12:00 pm Crowne Plaza Annapolis by IHG USD 18 FITNESS
Breathwork Healing Circle: A Guided Journey Inward Thu, 03 Dec at 06:30 pm 2158 Renard Ct FREE FITNESS
Ballet Theatre of Maryland presents "Momentum: A Mixed Bill" Fri, 19 Feb at 07:30 pm Maryland Hall USD 25 TO 100 FITNESS
Ballet Theatre of Maryland presents "Momentum: A Mixed Bill" Sat, 20 Feb at 07:00 pm Maryland Hall USD 25 TO 100 FITNESS
Data Analytics Certification Training in Annapolis, MD Wed, 22 Apr at 09:00 am Regus Business Center USD 1,484 TO 1,867 WORKSHOPS
Amelia White and Meg Murray in Annapolis Mon, 15 Mar at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23 FITNESS
Programming a Master Crystal Through Shamanic Journey with Audrey Rai Tue, 03 Nov at 07:00 pm Annapolis Crystals USD 50 WORKSHOPS
Ballet Theatre of Maryland - The Nutcracker at Maryland Hall for the Creative Arts Sat, 12 Dec at 01:00 pm Maryland Hall for the Creative Arts ART
Mini Performance of The Nutcracker by Ballet Theatre of Maryland Wed, 09 Dec at 09:30 am Maryland Hall USD 12 TO 17 FITNESS