Upcoming Live Music Events

War in Annapolis

 Rams Head On Stage 26 Sep 2025
ENTERTAINMENT

War in Annapolis

 Rams Head On Stage 25 Sep 2025
CONCERTS

The Wallflowers, Brother Elsey in Annapolis

 Rams Head On Stage 23 Sep 2025
ENTERTAINMENT

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Upcoming Festivals Events

35th Annual Kunta Kinte Heritage Festival

Navy–Marine Corps Memorial Stadium 13 Sep 2025
FESTIVALS

West Annapolis Oktoberfest 2025

 Annapolis Street, Annapolis, MD, United States, Maryland 21401 28 Sep 2025
OKTOBERFEST

BAYGRASS 2025: Annapolis Baygrass Music Festival 9/20-21

 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409 20 Sep 2025
MUSIC-FESTIVALS

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Upcoming Food & Drinks Events

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 7 Church Cir, Annapolis, MD, United States, Maryland 21401 12 Oct 2025
ENTERTAINMENT

Season Opening Celebration: Black and White Gala

 The Atreeum at Soaring Timbers 11 Sep 2025
FOOD-DRINKS

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 7 Church Cir, Annapolis, MD, United States, Maryland 21401 21 Sep 2025
ENTERTAINMENT

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Upcoming Halloween Events

Undead Mile Run – Annapolis, MD

 Annapolis, Annapolis, Maryland 25 Oct 2025
PARTIES

Annapolis Skelly Run

 Annapolis, Annapolis, Maryland 4 Oct 2025
HALLOWEEN

Annapolis Midnight Mile Vampire Run

 Annapolis, Annapolis, Maryland 11 Oct 2025
TRIPS-ADVENTURES

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Upcoming Parades Events

Annapolis Pride Parade and Festival

 Maryland Hall 18 Oct 2025
FESTIVALS

Eastport Yacht Club Lights Parade

 Historic Downtown Annapolis 13 Dec 2025
PARADES

Annapolis Maryland Pride

 Maryland Hall 18 Oct 2025

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Upcoming Music Festivals Events

Dirty Heads, Ballyhoo!, Wheeland Brothers in Annapolis

 Calvert Street Stage 12 Sep 2025
CONCERTS

Skerryvore in Annapolis

 Rams Head On Stage 8 Sep 2025
CONCERTS

Lily Grace Live @ Annapolis Songwriters Festival 2025

 33 West St, Annapolis, MD 21401-2574, United States 12 Sep 2025
FESTIVALS

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Upcoming Comedy Events

Michael Yo at Rams Head On Stage

 Rams Head On Stage 21 Sep 2025
TRIPS-ADVENTURES

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

 Stan & Joe's Saloon 19 Sep 2025
COMEDY USD 23

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

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Trending Events in Annapolis

Barktoberfest Annapolis 2025

 1906 Towne Centre Blvd 4 Oct 2025
DOG USD 0 TO 13

Annapolis Oktoberfest

 Annapolis St, Annapolis, MD, United States 28 Sep 2025
OKTOBERFEST

Pure Prairie League in Annapolis

 Rams Head On Stage 5 Dec 2025
ART

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

 Maryland Hall for the Creative Arts 11 Oct 2025
MUSIC

DIRTY HEADS w. Ballyhoo! & Wheeland Brothers

 44 Calvert St, Annapolis, MD 21401-1930, United States 12 Sep 2025
ENTERTAINMENT

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
CONCERTS

3hr Sunset Cruise w/ Live Entertainment from: KEVIN LEE

 Annapolis, MD 20 Sep 2025
MUSIC

Pure Prairie League in Annapolis

 Rams Head On Stage 5 Dec 2025
ENTERTAINMENT

10,000 Maniacs

 Rams Head On Stage 13 Sep 2025
MUSIC

10000 Maniacs at Rams Head On Stage

 Rams Head On Stage 13 Sep 2025
TRIPS-ADVENTURES

Mental Health and Wellness Resource Fair!

 2158 Renard Ct 18 Oct 2025
HEALTH-WELLNESS FREE

Leftover Salmon

 Rams Head On Stage 5 Oct 2025
TRIPS-ADVENTURES

Chris Standring in Annapolis

 Rams Head On Stage 10 Sep 2025
CONCERTS

Maysa (8:30 PM)

 Rams Head On Stage 20 Sep 2025
MUSIC

Keb' Mo' in Annapolis

 Maryland Hall 21 Nov 2025
CONCERTS

More things to do in Annapolis

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