Upcoming Festivals Events

Pressing Strings

 Rams Head On Stage 28 Dec 2025
MUSIC

Annapolis Color Run By Color Craze

 Downtown Annapolis 9 May 2026
FESTIVALS

The Young Fables in Annapolis, MD

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

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Upcoming Live Music Events

2026 Annapolis St. Patrick's Hooley!

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

Siren's Call

 The Westin Annapolis 26 Dec 2025
MUSIC FREE

Scorpion Rose

Blackwall Hitch - Annapolis 20 Dec 2025
MUSIC

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Upcoming New Year Events

NYE at Charthouse Prime Restaurant Annapolis

 Charthouse Restaurant Annapolis 31 Dec 2025
NEW-YEAR

New Year's Eve Annapolis Yacht Party

 1 Dock St, Annapolis, MD, United States, Maryland 21401 31 Dec 2025
NEW-YEAR

The Choptank's New Years Eve Party

 The Choptank - Annapolis 31 Dec 2025
NEW-YEAR USD 143 TO 228

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Upcoming Food & Drinks Events

New Year's Eve at Acqua al 2

 Acqua al 2 - Annapolis, Main Street, Annapolis, MD, USA 31 Dec 2025
NEW-YEAR USD 150

A Fright Before Christmas - Ghost Story Dinner at Middleton Tavern

 Middleton Tavern 23 Dec 2025
WORKSHOPS

Jimmie's Chicken Shack Holidaze Show

 Rams Head On Stage 26 Dec 2025
MUSIC

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Upcoming Christmas Markets & Fairs Events

Midnight Madness in Downtown Annapolis 2025

 Downtown Annapolis 18 Dec 2025
HOLIDAY

Heroes Holiday Market

 1 Riverview Avenue, Annapolis, MD 14 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS

ANNAPOLIS HOLIDAY MARKET w/ SANTA & The Wish Crackler - St. John's College - Annapolis, Maryland

 St. John's College 18 Dec 2025
HOLIDAY

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Upcoming Comedy Events

Holiday Improv Comedy Show - Annapolis Maryland

 ArtFarm 20 Dec 2025
PERFORMANCES USD 10

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025
BRUNCH

Paula Poundstone at Rams Head On Stage

 Rams Head On Stage 19 Dec 2025

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Trending Events in Annapolis

A Longest Night Service

 Eastport United Methodist Church 21 Dec 2025
CHRISTMAS

Share the Light & Joy of Christmas at St. Luke's: Christmas Eve

1101 Bay Ridge Ave, Annapolis, MD, United States, Maryland 21403 24 Dec 2025
CHRISTMAS

Candlelight: Christmas Carols on Strings | Annapolis

 Annapolis Waterfront Hotel 21 Dec 2025
CHRISTMAS-CAROLS

Caroling at Oscar's

 Oscar’s Coffee 24 Dec 2025
CHRISTMAS-CAROLS

Maryland Day Celebration 2026 - filled with fun events!

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

Ballet Theatre of Maryland presents "The Nutcracker"

 Maryland Hall 20 Dec 2025
ART USD 47 TO 72

7th Annual Bubbly Bridal Expo & 1000+ Gown Sale!

Graduate Annapolis 25 Jan 2026
EXHIBITIONS

New Years Eve Cruise 2026

 680 Americana Dr 31 Dec 2025
NEW-YEAR USD 107

Get Closer: Couples Tantra Workshop

 groundswell yoga annapolis 6 Feb 2026
WORKSHOPS USD 232 TO 290

An Annapolis Christmas

 Rams Head On Stage 14 Dec 2025
CHRISTMAS

Brunch with Santa

 33 West St, Annapolis, MD, United States, Maryland 21401 14 Dec 2025
BRUNCH

Ballet Theatre of Maryland - The Nutcracker at Maryland Hall for the Creative Arts

 Maryland Hall for the Creative Arts 13 Dec 2025
ART

Brunch with Santa

 Rams Head Roadhouse 14 Dec 2025
BRUNCH

Last Train Home

 Rams Head On Stage 2 Jan 2026
MUSIC

Holiday Virtual Charity Wine Dinner

 36 West St, Annapolis, MD, United States, Maryland 21401 14 Dec 2025
NONPROFIT

More things to do in Annapolis

Festivals
Live Music
New Year
Food & Drinks
Christmas Markets & Fairs
Comedy
Parades
Christmas Carols
Christmas Services
Fireworks
Music Festivals
Bar Crawls
Christmas Wreath Workshops
Job Fairs
Christmas Parades
Boat Parties