Upcoming Live Music Events

Pure Prairie League in Annapolis

 Rams Head On Stage 5 Dec 2025
ART

Pure Prairie League in Annapolis

 Rams Head On Stage 5 Dec 2025
ENTERTAINMENT

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
CONCERTS

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Upcoming Food & Drinks Events

Siren's Call

 The Westin Annapolis 5 Dec 2025
MUSIC FREE

Siren's Call

 The Westin Annapolis 19 Dec 2025
MUSIC FREE

Siren's Call

 The Westin Annapolis 12 Dec 2025
MUSIC FREE

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Upcoming Festivals Events

Annapolis Chocolate Binge Festival

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

Brunch with Santa

 Rams Head Roadhouse 14 Dec 2025
BRUNCH

Brunch with Santa

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

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Upcoming Thanksgiving Events

FRI 11/28/25: Black Friday MIDNIGHT MADNESS + ALL DAY DEALS At Third Eye!

 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 28 Nov 2025
BLACK-FRIDAY

Broadneck Class of 2015

 Metropolitan Kitchen & Lounge 29 Nov 2025
WORKSHOPS USD 66

Thanksgiving Eve Service at St. Luke's

 1101 Bay Ridge Ave, Annapolis, MD, United States, Maryland 21403 26 Nov 2025
THANKSGIVING

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Upcoming Christmas Markets & Fairs Events

Midnight Madness West Street Artisan Holiday Market

 60 West St, Annapolis, MD 21401-2434, United States 11 Dec 2025
HOLIDAY

A Colonial Yuletide

 186 Prince George St, Annapolis, MD 21401-1724, United States 6 Dec 2025
HOLIDAY

Annapolis Italian Christmas Market 2025

 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 7 Dec 2025
CHRISTMAS

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Upcoming New Year Events

New Year's Eve Annapolis Yacht Party

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

NYE at Charthouse Prime Restaurant Annapolis

 Charthouse Restaurant Annapolis 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 Bar Crawls Events

Witches of Maryland Pub Crawl

Downtown Anapolis 29 Nov 2025
PARTIES

Hidden History Pub Crawl

 16 Church Cir, Annapolis, MD 21401-1927, United States 28 Nov 2025
PARTIES

5th Annapolis Santa Stroll from Peake Social!

 Annapolis 6 Dec 2025
HOLIDAY USD 0 TO 7

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Upcoming Comedy Events

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

Paula Poundstone

 Rams Head On Stage 18 Dec 2025
CALENDAR

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Trending Events in Annapolis

Annapolis Holiday of Lights Boat Parade

 680 Americana Dr 13 Dec 2025
CHRISTMAS-PARADES USD 107

Annapolis Holiday Boat Parade

 110 Compromise St, Annapolis, MD 21401-1828, United States 13 Dec 2025
CHRISTMAS-PARADES

Nutcracker Tea 2025

DoubleTree by Hilton Hotel Annapolis 7 Dec 2025
HOLIDAY

Chris Isaak in Annapolis

 Maryland Hall 7 Dec 2025
CONCERTS

The Moonshiners Ball 2025 A Cocktail Party for the SPCA and Slade Child Foundation.

 Latitude 38 Annapolis 7 Dec 2025
ENTERTAINMENT

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

Graduate Annapolis 25 Jan 2026
EXHIBITIONS

Family Karaoke Sunday - Powered by DJ KJ Ben

 Caliente Grill 7 Dec 2025
KARAOKE FREE

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
ART

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Rams Head On Stage 4 Dec 2025
CONCERTS

Sold Out: Breakfast with Santa

 400 6th St, Annapolis, MD, United States, Maryland 21403 6 Dec 2025
BREAKFAST-WITH-SANTA

Get Closer: Couples Tantra Workshop

 groundswell yoga annapolis 6 Feb 2026
WORKSHOPS USD 232 TO 290

Atlanta Rhythm Section in Annapolis

 Rams Head On Stage 6 Dec 2025
CONCERTS

Hotel Paradise (Dance Area!)

Rams Head On Stage 30 Nov 2025
ENTERTAINMENT

Tab Benoit: I Hear Thunder Tour w/ Jesse Dayton

 Rams Head On Stage 7 Dec 2025
MUSIC

More things to do in Annapolis

Live Music
Food & Drinks
Festivals
Thanksgiving
Christmas Markets & Fairs
New Year
Bar Crawls
Christmas Parades
Fireworks
Comedy
Christmas Wreath Workshops
Christmas Carols
Parades
Christmas Light Displays
Music Festivals
Boat Parties
Pop-Ups