Annapolis Festivals Events

2025 Hall & Friends Oyster Roast

Bay Ridge Marina 1 Nov 2025

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 2 Nov 2025

Annapolis Chocolate Binge Festival

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

The Great Annapolis Gingerbread Houses Contest

26 West St, Annapolis, MD 21401-2421, United States 22 Nov 2025

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

Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon

Stan & Joe's Saloon 15 Nov 2025

SAMHAIN- 2025

Unitarian Universalist Church of Annapolis 1 Nov 2025

Deadgrass, Bluegrass Covers of The Grateful Dead

Annapolis Mall 11 Nov 2025

The Doug Segree Band at 49 West

49 West St, Annapolis, MD 21401-2420, United States 17 Nov 2025

Sister Hazel (matinee)

Rams Head On Stage 15 Nov 2025

Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon

Stan & Joe's Saloon 14 Nov 2025

U2topia: The Mid-Atlantic U2 Tribute Band

Rams Head On Stage 28 Nov 2025

Joshua Redman Quartet

801 Chase St, Annapolis, MD, United States, Maryland 21401 16 Nov 2025

Annapolis Jazz & Roots Festival - Michael McHenry Tribe

Pip Moyer Recreation Center at Truxtun Park 9 Nov 2025

Annapolis Jazz & Roots - Ed Hrybyk "Bass Traditions"

Anne Arundel County Public Library (Eastport-Annapolis Neck Library) 15 Nov 2025

Pressing Strings

Rams Head On Stage 28 Dec 2025

PARKING: Military Bowl

Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025

Taste of Fall on West Street

53 West St 9 Nov 2025

Annapolis Jazz & Roots Festival - Footworks Percussive Dance Ensemble

Unitarian Universalist Church of Annapolis 15 Nov 2025

Annapolis Jazz & Roots Festival JC Jefferson - Salute to Quincy Jones

Banneker-Douglass-Tubman Museum 8 Nov 2025

Annual Kwanzaa Celebration

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

Annapolis Jazz & Roots Festival "Art Music & the Muse" Artist talk - Jabari and JC Jefferson

Banneker-Douglass-Tubman Museum 8 Nov 2025

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025

Here's to Heroes!

155 Main St, Annapolis, MD, United States, Maryland 21401 4 Nov 2025

Annapolis Jazz & Roots Festival Alexis Tantau & Letitia VanSant with Rusty Sal - Eva Cassidy Tribute

Peerless Rens Club 7 Nov 2025

Parking Military Bowl

Navy-Marine Corps Memorial Stadium 27 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