Association Strategic Partner

City of Annapolis Events

160 Duke of Gloucester St., Annapolis, MD 21401
(410) 263-7997
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About City of Annapolis Events

May Day In Annapolis
City of Annapolis Events

May Day In Annapolis

May 1, 2019

The 63nd annual May Day basket competition, sponsored by the Garden Club of Old Annapolis Town, will be held May 1 in celebration of May Day.  Residents and merchants in throughout the City will arrange baskets of fresh cut flowers to display outside their homes and businesses throughout the day. Displays will be out by 10:00 a.m. throughout the area. This is a rain or shine event. 

Annapolis New Year’s Eve Celebration
City of Annapolis Events

Annapolis New Year’s Eve Celebration

December 31, 2018

Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year. Kids’ activities will take place with activities that include face painting, an obstacle course, moon bounces and live music. The festivities wraps up with on-site fireworks for the kids,then, it’s off to area restaurants for dinner with the kids. The second round of festivities includes live music and dancing at Susan Campbell Park at City Dock beginning at 8:00 p.m. and ending with midnight fireworks.

The Grand Illumination
City of Annapolis Events

The Grand Illumination

November 25, 2018

The Downtown Annapolis Partnership joins the Annapolis Jaycees as they ring in the holiday season in downtown Annapolis.  The Grand Illumination and annual tree lighting takes place at the Market House starting at 5:30 pm with dancing and carols by local school groups.  Santa arrives to help light the tree around 6:30 pm and help get everyone in the holiday spirit. The Jaycees serve hot chocolate and candy canes and  have ornaments for children to decorate. The Jaycees also accept donations of unwrapped toys and non-perishable food items for their annual Angel Tree program, which helps local families in need during the holiday season.

Maritime Republic of Eastport's Tug of War
City Dock, Annapolis & 2nd Street, Eastport

Maritime Republic of Eastport's Tug of War

November 3, 2018

Billed as the longest International Tug of War over water in the world, The Tug of War was originally conceived by the residents of Eastport in 1997 when the City of Annapolis used the excuse of a "public works project" to close the Spa Creek bridge that leads to Eastport from Annapolis. This unprovoked act of aggression on the part of the City of Annapolis had the effect of cutting off Eastport residents and businesses from the rest of the city. The somewhat fractious citizens of Eastport, feeling the sting of rejection by The City and, perhaps, somewhat emboldened by the generous pouring habits of a local bartender, decided to declare war against The City of Annapolis and secede. Thus, to the rallying cries of "Up The Republic," the micro-nation known as The Maritime Republic of Eastport was born. In the ensuing years, although the Spa Creek Bridge has since re-opened, the once persecuted citizens of Eastport (Eastport-O-Ricans) have yearly declared a symbolic War of Independence against The City of Annapolis lest anyone forget this dark period of Annapolis-Eastport relations. The Tug of War, a celebration of the geographical and, some would argue, philosophical differences between Eastport and Annapolis, is a not-to-be missed maritime event unlike any other.

Annapolis Italian Festival
Annapolis Sons of Italy Lodge

Annapolis Italian Festival

September 30, 2018

Come enjoy the 4th Annual Annapolis Italian Festival, in honor of the patron saint of Italian immigrants, Mother Cabrini. Delicious Italian foods like pasta, calamari, and sub-sandwiches as well as homemade desserts like cannoli and zeppole will be offered.  Live mozzarella and limoncello demonstrations will be shown. Continuous music, face painting and vendors of Italian cars, novelties, photos and apparel will also be available. The Sons of Italy is a nonprofit, fraternal organization whose proceeds support local charities and scholarship funds.