Shopping Events in Annapolis

Annapolis Chocolate Binge Festival

Sun, 06 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

FESTIVALS

Mad Cute Market 🍂 Gilmore Girls Autumn

Fri, 20 Nov at 05:00 pm 730 Bestgate Rd

FESTIVALS

Annapolis Holiday Market

Fri, 04 Dec at 11:00 am Annapolis Mall

FITNESS

Black Friday & Small Business Saturday @ The Spice & Tea Exchange of Annapolis

Fri, 27 Nov at 07:00 pm The Spice & Tea Exchange of Annapolis

Heroes & Helpers: Holiday Shop with a Cop

Sat, 05 Dec at 09:00 am Outback Steakhouse (2207 Forest Drive, Annapolis, MD)

Heroes Holiday Market

Sun, 06 Dec at 08:00 am 1 Riverview Avenue, Annapolis, MD

HOLIDAY

Winter Wonderjam

Sat, 28 Nov at 12:00 pm Dark Horse Annapolis

MUSIC

Holiday Shopping & Community Meetup at HomeSense Annapolis

Sun, 06 Dec at 08:00 am Homesense

FREE HOLIDAY

WED 11/25/26: Third Eye Holiday Homecoming / Games Giving!

Wed, 25 Nov at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

NONPROFIT

Harbor Hustle

Fri, 25 Sep at 10:00 am 1 Dock St

USD 23 FITNESS

FRI 11/27/26: Black Friday Midnight Madness and All Day Deals at Third Eye

Thu, 26 Nov at 11:59 pm 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

SAT 11/28/26: Third Eye Ride Or Die! Small Business Saturday

Sat, 28 Nov at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

CONTESTS

Here's to Heroes!

Tue, 03 Nov 155 Main St, Annapolis, MD, United States, Maryland 21401

FESTIVALS