Weekly and upcoming Events
- Trivia Night at 1747 Pub - Every Monday
- Live Music at Brian Boru - Every Thursday, Friday, Saturday
- Live Music at Killarney House - Every Friday and Saturday
May 2016
- Commissioning Week - May 20 - 27
- Kent Island Day - May 21
- Chesapeake Bay Blues Festival - May 21 - 22
- Blue Angels Flight Demonstration - May 24 - 25
- Naval Academy Graduation & Commissioning - May 27
- Memorial Day Parade & Ceremony - May 30
- Paint Annapolis - May 31 - June 5
June 2016
- Annapolis Greek Festival - June 2- 5
- Leukemia Cup Regatta - June 3 - 4
- Annapolis Arts, Crafts and Wine Festival - June 4 -5
- Strawberry Festival - June 4
- Bay Music Festival - June 11
- Great Chesapeake Bay Swim - June 12
- Home and Garden Tour - June 12
- Eastport-a-Rockin' - June 18
July 2016
- First Sunday Arts Festival - July 3
- Annapolis 4th of July Parade - July 4
- United States Naval Academy Band Performance - July 4
- 4th of July Fireworks - July 4
- Independence Day Fireworks Cruise - July 4
- Hammond-Harwood House Full Moon Tour - July 15
- Annapolis Irish Festival - July 15-16
August 2016
- Annapolis Crab Feast - August 5
- First Sunday Arts Festival - August 7
- The 26th Annual Annapolis Art Walk - August 18
- Maryland Renaissance Festival - August 27-October 23
- Annapolis 10 Mile Run - August 28
September 2016
- Maryland Renaissance Festival - until October 23
- Navy Football Game (vs. Fordham University) - September 3
- First Sunday Arts Festival - September 4
- Labor Day Parade - September 5
- Navy Football Gam (vs. University of Connecticut) - September 10
- Maryland Seafood Festival - September 10-11
- Anne Arundel County Fair - September 14-18
- Hammond-Harwood House Full Moon Tour - September 16
- Boatyard Beach Bash - September 17
- Maryland Avenue/State Circle Fall Festival - September 17
- Craft Beer and Music Festival - September 17
- Annapolis Fringe Festival - September 21-24
- Kunta Kinte Heritage Festival - September 26
- Homestead Gardens Annual Fall Festival - September 24 - October 30
October 2016
- Maryland Renaissance Festival - until October 23
- Historic Hauntings Tour - October 1-30
- First Sunday Arts Festival - October 2
- United States Sailboat Show - October 6-10
- Navy Football Game (vs. University of Houston) - October 8
- United States Powerboat Show - October 13-16
- Patuxent Wildlife Festival - October 15
- Oyster Festival - October 16
- Navy Football Game (vs. University of Memphis) - October 22
November 2016
- Annapolis by Candlelight - November 4-5
- Eastport's Tug o' War - November 5
- First Sunday Arts Festival - November 6
- Run Across the Bay 10K - November 6
- Art Between the Creeks - November 6-8
- Veterans Classic - November 11
- Navy Football Game (vs. University of Tulsa) - November 12
- Lights on the Bay - November 19 - Jan 1
- Grand Illumination - City Tree Lighting - November 27
December 2016
- Lights on the Bay - Until Jan 1
- Midnight Madness Holiday Shopping - December 1, 8 & 15
- First Sunday Arts Festival - December 4
- Eastport Yacht Club Lights Parade - December 10
- Military Bowl - December 27
- City of Annapolis New Year's Eve Celebration - December 31
Monthly Events
- The "America's 14 Forgotten Presidents of Congress Before Washington" Exhibit
- Market Space Music Festival - 3rd Sundays Historic Downtown Annapolis Sitting at the Dock of the Bay!
Taking Place at Ram's Head
- Jazz Brunch - Every Sunday
- Free World Beer Club Membership - Every Tuesday