Annapolis Festivals Events
Festivals Happening Next in Annapolis, MD
2025 Hall & Friends Oyster Roast
Bay Ridge Marina
1 Nov 2025
MUSIC
First Sunday Arts Festival
Calvert and West Streets, Annapolis, MD, United States, Maryland 21401
2 Nov 2025
FESTIVALS
Annapolis Chocolate Binge Festival
53 West St, Annapolis, MD 21401-2420, United States
7 Dec 2025
MUSIC
The Great Annapolis Gingerbread Houses Contest
26 West St, Annapolis, MD 21401-2421, United States
22 Nov 2025
CONTESTS
Pete Correale at Rams Head On Stage
Rams Head On Stage
7 Nov 2025
The Carole King & James Taylor Story
Rams Head On Stage
15 Nov 2025
MUSIC
Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon
Stan & Joe's Saloon
15 Nov 2025
COMEDY
USD 23
SAMHAIN- 2025
Unitarian Universalist Church of Annapolis
1 Nov 2025
Deadgrass, Bluegrass Covers of The Grateful Dead
Annapolis Mall
11 Nov 2025
ENTERTAINMENT
USD 34
The Doug Segree Band at 49 West
49 West St, Annapolis, MD 21401-2420, United States
17 Nov 2025
ENTERTAINMENT
Sister Hazel (matinee)
Rams Head On Stage
15 Nov 2025
MUSIC
Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon
Stan & Joe's Saloon
14 Nov 2025
COMEDY
USD 23
U2topia: The Mid-Atlantic U2 Tribute Band
Rams Head On Stage
28 Nov 2025
ENTERTAINMENT
Joshua Redman Quartet
801 Chase St, Annapolis, MD, United States, Maryland 21401
16 Nov 2025
MUSIC
Annapolis Jazz & Roots Festival - Michael McHenry Tribe
Pip Moyer Recreation Center at Truxtun Park
9 Nov 2025
MUSIC
Annapolis Jazz & Roots - Ed Hrybyk "Bass Traditions"
Anne Arundel County Public Library (Eastport-Annapolis Neck Library)
15 Nov 2025
MUSIC
Pressing Strings
Rams Head On Stage
28 Dec 2025
MUSIC
PARKING: Military Bowl
Navy Marine Corps Memorial Stadium Parking Lots
26 Dec 2025
TRIPS-ADVENTURES
Taste of Fall on West Street
53 West St
9 Nov 2025
MUSIC
USD 7 TO 82
Annapolis Jazz & Roots Festival - Footworks Percussive Dance Ensemble
Unitarian Universalist Church of Annapolis
15 Nov 2025
MUSIC
Annapolis Jazz & Roots Festival JC Jefferson - Salute to Quincy Jones
Banneker-Douglass-Tubman Museum
8 Nov 2025
MUSIC
Annual Kwanzaa Celebration
84 Franklin St, Annapolis, MD, United States, Maryland 21401
13 Dec 2025
FESTIVALS
Annapolis Jazz & Roots Festival "Art Music & the Muse" Artist talk - Jabari and JC Jefferson
Banneker-Douglass-Tubman Museum
8 Nov 2025
MUSIC
The Empty Pockets at Rams Head On Stage
Rams Head On Stage
3 Dec 2025
CALENDAR
Here's to Heroes!
155 Main St, Annapolis, MD, United States, Maryland 21401
4 Nov 2025
FESTIVALS
Annapolis Jazz & Roots Festival Alexis Tantau & Letitia VanSant with Rusty Sal - Eva Cassidy Tribute
Peerless Rens Club
7 Nov 2025
MUSIC
Parking Military Bowl
Navy-Marine Corps Memorial Stadium
27 Dec 2025
CALENDAR
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
TRIPS-ADVENTURES
2025 Lights on the Bay MD with the SPCA of Anne Arundel County
Sandy Point State Park
23 Nov 2025
HOLIDAY
USD 23 TO 100
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