Upcoming Live Music Events

2026 Annapolis St. Patrick's Hooley!

 U.S. Naval Academy Alumni Association & Foundation 7 Mar 2026
POP USD 178

John Moreland & Patterson Hood

 Rams Head On Stage 14 Mar 2026
CONTESTS

John Moreland and Patterson Hood

 Rams Head On Stage - Annapolis 15 Mar 2026
TRIPS-ADVENTURES

View More Live Music Events

Upcoming Festivals Events

Maryland Day Celebration 2026 - filled with fun events!

 Across Annapolis & Anne Arundel County, MD, United States, Maryland 19 Mar 2026

The Young Fables in Annapolis, MD

 49 West Coffeehouse, Winebar & Gallery 20 Feb 2026
ENTERTAINMENT USD 23

Historic Annapolis Maryland Day Celebrations

 99 Main Street, Annapolis, MD, United States, Maryland 21401 21 Mar 2026

View More Festivals Events

Upcoming Valentine's Day Events

Emmaline: LIVE in Annapolis, MD "Be My Valentine" Tour

Rams Head On Stage 15 Feb 2026
MUSIC

Valentine's Day Dinner

 Captain's Daughter 14 Feb 2026
VALENTINES-DAY FREE

Valentine's Dinner (Dine in or Carryout)

 36 West St, Annapolis, MD, United States, Maryland 21401 14 Feb 2026
VALENTINES-DAY

View More Valentine's Day Events

Upcoming Food & Drinks Events

Paul Gilbert with Greg Koch

 Rams Head On Stage - Annapolis 13 May 2026
CONTESTS

Superbowl Sunday

 Captain's Daughter 8 Feb 2026
SPORTS FREE

Naptown Flea Vintage & Vinyl

 801 Chase St 1 Feb 2026
FLEA FREE

View More Food & Drinks Events

Upcoming Galentines Day Events

Galentine’s Day: A Celebration of Community

Crowne Plaza Annapolis 8 Feb 2026
GALENTINES-DAY

Galentine’s Night Market & Social

 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 6 Feb 2026
NIGHT-MARKETS

Galentine’s Bottle Painting Experience

 Caliente Grill 7 Feb 2026
ART USD 66

View More Galentines Day Events

Upcoming Music Festivals Events

Chesapeake Winter Bluegrass FESTIVAL

 Crowne Plaza Annapolis 30 Jan 2026
FESTIVALS

Annapolis Color Run By Color Craze

 Downtown Annapolis 9 May 2026
FESTIVALS

Songbird Festival 2026

 Maryland Hall 3 May 2026
FESTIVALS FREE

View More Music Festivals Events

Upcoming Comedy Events

Comics for Critters

 Federal House Bar & Grille 9 Feb 2026
COMEDY USD 23 TO 215

Capitol Fools at Rams Head On Stage

 Rams Head On Stage 7 Feb 2026
CONTESTS

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

 Stan & Joe's Saloon 20 Feb 2026
COMEDY USD 23

View More Comedy Events

Upcoming St. Patrick's Day Events

Emerald Society Annapolis St Patrick’s Parade Group

 Stan and Joe's Saloon 8 Mar 2026
SAINT-PATRICKS-DAY

4th Annual Peake Irish Experience for Annapolis St Patrick's Day on 3/7

 Main Street 7 Mar 2026
NONPROFIT USD 7 TO 29

The Official Annapolis Shamrock Stroll

 The Best Bars in Annapolis 7 Mar 2026
PARTIES USD 5

View More St. Patrick's Day Events

Upcoming Mardi Gras Events

Naptown Brass Band Mardi Gras at Rams Head!!!

 Rams Head On Stage 17 Feb 2026
ENTERTAINMENT

Masquerade Party

 Captain's Daughter 17 Feb 2026
PARTIES FREE

Mardi Gras @ Forward Brewing

 926 Bay Ridge Ave, Annapolis, MD, United States, Maryland 21403 17 Feb 2026
MARDI-GRAS

View More Mardi Gras Events

Trending Events in Annapolis

Matisyahu

 Rams Head On Stage 3 Mar 2026
CALENDAR

Black Violin: Full Circle at Rams Head On Stage

 Rams Head On Stage 28 Feb 2026
MUSIC

Black Violin

 Rams Head On Stage 27 Feb 2026
MUSIC

Graham Nash at Maryland Hall for the Creative Arts

 Maryland Hall for the Creative Arts 14 Apr 2026
TRIPS-ADVENTURES

Amish Outlaws

 Rams Head On Stage 6 Mar 2026

Marcus Miller at Rams Head On Stage

 Rams Head On Stage 24 May 2026
CONTESTS

Dan Tyminski Band at Rams Head On Stage

 Rams Head On Stage 13 Feb 2026
MUSIC

The High Kings at Rams Head On Stage

 Rams Head On Stage 8 Mar 2026
TRIPS-ADVENTURES

Madeleine Peyroux at Rams Head On Stage

 Rams Head On Stage 11 May 2026
CONTESTS

Spyro Gyra

 Rams Head On Stage 4 Mar 2026
CONTESTS

Dar Williams & Seth Glier

 Rams Head On Stage 5 Feb 2026
CONTESTS

Joanne Shaw Taylor at Rams Head On Stage

 Rams Head On Stage 28 Mar 2026
TRIPS-ADVENTURES

Parking Colgate Raiders at Navy Midshipmen Mens Basketball

 Alumni Hall - Navy 28 Feb 2026
CALENDAR

G Love and Special Sauce at Rams Head On Stage

 Rams Head On Stage 3 Feb 2026
TRIPS-ADVENTURES

Jonathan Butler at Rams Head On Stage

 Rams Head On Stage 18 Apr 2026
CALENDAR

More things to do in Annapolis

Live Music
Festivals
Valentine's Day
Food & Drinks
Galentines Day
Music Festivals
Comedy
St. Patrick's Day
Mardi Gras
Bar Crawls
Parades
Black History Month
Presidents Day
Super Bowl
Job Fairs
Pop-Ups