Upcoming Live Music Events

Pure Prairie League in Annapolis

 Rams Head On Stage 5 Dec 2025
ART

Najee in Annapolis

 Rams Head On Stage 9 Nov 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
CONCERTS

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Upcoming Food & Drinks Events

Party in the Port

 317 First St, Annapolis, MD, United States, Maryland 21403 11 Oct 2025
ENTERTAINMENT

Siren's Call

 The Westin Annapolis 10 Oct 2025
MUSIC FREE

Siren's Call

 The Westin Annapolis 17 Oct 2025
MUSIC FREE

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Upcoming Festivals Events

Full Moon Celebration - November

 Unitarian Universalist Church of Annapolis 7 Nov 2025
HEALTH-WELLNESS

Four80East

 Rams Head On Stage 24 Oct 2025
TRIPS-ADVENTURES

Annapolis Pride Parade and Festival

 Maryland Hall 18 Oct 2025
FESTIVALS

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Upcoming Halloween Events

Undead Mile Run – Annapolis, MD

 Annapolis, Annapolis, Maryland 25 Oct 2025
PARTIES

Annapolis Midnight Mile Vampire Run

 Annapolis, Annapolis, Maryland 11 Oct 2025
TRIPS-ADVENTURES

Witches of Maryland Pub Crawl

Downtown Anapolis 12 Oct 2025
PARTIES

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Upcoming Comedy Events

Technicolor Motor Home

 Rams Head On Stage 12 Oct 2025
MUSIC

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 7 Church Cir, Annapolis, MD, United States, Maryland 21401 26 Oct 2025
ENTERTAINMENT

Dracula: A Comedy of Terrors

 108 East St, Annapolis, MD, United States, Maryland 21401 24 Oct 2025
COMEDY

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Upcoming Music Festivals Events

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

RICKSHAW LIZARD live at DragonFest - breast cancer benefit!

 Pier 4 Marina 11 Oct 2025
MUSIC

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Upcoming Parades Events

Eastport Yacht Club Lights Parade

 Historic Downtown Annapolis 13 Dec 2025
PARADES

Annapolis Maryland Pride

 Maryland Hall 18 Oct 2025

✊March with PFLAG Southern Maryland at Annapolis Pride🏳️‍🌈

 College Ave, Annapolis, MD 21401, United States 18 Oct 2025
PARADES

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Trending Events in Annapolis

Celebrate You

 Annapolis Town Center 11 Oct 2025
HEALTH-WELLNESS FREE

Wellness on the Green with Toastique Annapolis

 Annapolis Town Center 17 Apr 2025
HEALTH-WELLNESS FREE

Spirits of the Past: Death, Disease & Mourning Tours

 186 Prince George St, Annapolis, MD 21401-1724, United States 11 Oct 2025
CANDLELIGHT-CONCERTS

Candlelight: Halloween Classics | Annapolis

 Maryland Hall 30 Oct 2025
CANDLELIGHT-CONCERTS

Signature Series: A New World with Pablo Sainz-Villegas, guitar

 Maryland Hall for the Creative Arts 11 Oct 2025
MUSIC

Pure Prairie League in Annapolis

 Rams Head On Stage 5 Dec 2025
ENTERTAINMENT

Mystery Art Making at ArtFarm

 ArtFarm 10 Oct 2025
ART USD 71

Keb' Mo' in Annapolis

 Maryland Hall 21 Nov 2025
CONCERTS

Mental Health and Wellness Resource Fair!

 2158 Renard Ct 18 Oct 2025
HEALTH-WELLNESS FREE

Najee in Annapolis

 Rams Head On Stage 9 Nov 2025
CONCERTS

Technicolor Motor Home - A Steely Dan Tribute

 Rams Head On Stage 11 Oct 2025
TRIPS-ADVENTURES

*SOLD OUT* The Ocean Blue w/ Brian Tighe of The Hang Ups

 Rams Head On Stage 10 Oct 2025
MUSIC

2025 Shore Party

 Safe Harbor Annapolis 1 Nov 2025
PARTIES

A2B Offshore Racing Safety Seminar

 317 First Street , Annapolis, MD, United States, Maryland 21403 15 Nov 2025
SPORTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
CONCERTS

More things to do in Annapolis

Live Music
Food & Drinks
Festivals
Halloween
Comedy
Music Festivals
Parades
Candlelight Concerts
Pop-Ups
Bastille Day
Oktoberfest