Downtown Annapolis Events, Festivals and Traditions


New Years Day Resolution Run
City Dock


Annapolis Restaurant Week


Eastport Green Beer Races

St Patrick’s Day in Annapolis
Join us because that day every bar is Irish!

Maryland Day
Know Your Maryland!

March Madness
Downtown Shopping Event


Annapolis Rockfish Tournament

St. John’s – U.S. Naval Academy
Croquet Match

Maryland Avenue
Spring Fling Festival


Annual May Day Baskets
May 1 – Walk historic downtown and enjoy this European tradition celebrating spring!

Annapolis Maritime Festival

Downtown Annapolis
Sunday Farmers Market

United States Naval Academy Commissioning Week

Blue Angels

Wednesday Night Sailboat Races
World Championship Sailboat Races

First Sundays
Historic West Street Festivals


Irish Festival
Maryland Avenue

Arts Between the Creeks


Paca Gardens Concert Series


Thursday Lunchtime Music Series
on City Dock

City of Annapolis
Fourth of July Fireworks

Market Space Music Festival
3rd Sundays – Historic downtown Annapolis
Sitting at the Dock of the Bay!


Annapolis Ten Miler

Annapolis Crab Feast
Navy-Marine Corps Memorial Stadium

Annapolis Art Walk


Labor Day Parade

Downtown Days

Navy Sporting Events

Annapolis Fall Festival

Alex Haley – Kunta Kinte Festival

Paint Annapolis




United States Sailboat Show United States Powerboat Show

Boat Show Breakdown Parade of Boats Watch the cheerful but exhausted salespeople depart in an exchange of boats the last hour of the sailboat show. Come watch the chaotic tradition from Pussers.

Oktober Fest
Our neighbor, village of West Annapolis

Annapolis Halloween Festival

Halloween Eve in Annapolis
Join us Downtown!


Tug Of War!
Annapolis VS Eastport


Midnight Madness
Downtown Shopping Event

Lighting of the Holiday Tree
Market Space

Annapolis Boat Parade of Lights

Holiday Madness
Village of West Annapolis

New Years Eve
City Celebration & Fireworks
City Dock!