Annapolis Festivals Events

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 7 Dec 2025

Brunch with Santa

Rams Head Roadhouse 14 Dec 2025

Brunch with Santa

33 West St, Annapolis, MD, United States, Maryland 21401 14 Dec 2025

U2topia: The Mid-Atlantic U2 Tribute Band

Rams Head On Stage 28 Nov 2025

Annapolis Color Run By Color Craze

Downtown Annapolis 9 May 2026

PARKING: Military Bowl

Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025

Pressing Strings

Rams Head On Stage 28 Dec 2025

The Young Fables in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 20 Feb 2026

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025

Annual Kwanzaa Celebration

84 Franklin St, Annapolis, MD, United States, Maryland 21401 13 Dec 2025

Anniversay Chocolate & Wine pairing

36 West St, Annapolis, MD, United States, Maryland 21401 7 Dec 2025

Marc Douglas Berardo and Grace Morrison in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 20 Apr 2026

Run Naptown Running Festival

Navy-Marine Corps Stadium 20 Dec 2025

G. Love & Special Sauce - Lemonade 20th Anniversary Tour with Special Guest MAKUA

Rams Head On Stage 4 Feb 2026

G. Love & Special Sauce- Lemonade 20th Anniversary Tour with Special Guest MAKUA

Rams Head On Stage 3 Feb 2026

Here's to Heroes!

155 Main St, Annapolis, MD, United States, Maryland 21401 2 Dec 2025

Maryland Day Week 2026 - filled with fun events!

Anne Arundel County, MD, United States, Maryland 19 Mar 2026

Burning Witches

Rams Head On Stage 31 Mar 2026

2025 Lights on the Bay MD with the SPCA of Anne Arundel County

Sandy Point State Park 23 Nov 2025