Upcoming Annapolis Events

Check out what's happening all around Annapolis, MD

Annapolis Holiday of Lights Boat Parade

 Sat, 13 Dec at 05:00 pm 680 Americana Dr USD 107

NYE at Charthouse Prime Restaurant Annapolis

 Wed, 31 Dec at 07:00 pm Charthouse Restaurant Annapolis

New Year's Eve Annapolis Yacht Party

 Wed, 31 Dec at 08:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Holiday Improv Comedy Show - Annapolis Maryland

 Sat, 20 Dec at 08:00 pm ArtFarm USD 10

The Choptank's New Years Eve Party

 Wed, 31 Dec at 08:00 pm The Choptank - Annapolis USD 143 to 228

2025 Santa Speedo Run

 Sat, 13 Dec at 11:00 am O'Brien's Oyster Bar & Seafood Tavern

New Year's Eve at Acqua al 2

 Wed, 31 Dec at 08:45 pm Acqua al 2 - Annapolis, Main Street, Annapolis, MD, USA USD 150

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

Sun, 25 Jan at 12:00 pm Graduate Annapolis

New Years Eve Cruise 2026

 Wed, 31 Dec at 10:00 pm 680 Americana Dr USD 107

Get Closer: Couples Tantra Workshop

 Fri, 06 Feb at 06:30 pm groundswell yoga annapolis USD 232 to 290

An Annapolis Christmas

 Sun, 14 Dec at 07:00 pm Rams Head On Stage

Holiday Music with Mark Berman, Pianist & Dave Richards, Bassist

 Sat, 13 Dec at 07:30 pm Annapolis Mall Free

Plyometric Power (half) Hour with Dr. Maddie Fischer

 Fri, 19 Dec at 07:00 pm lululemon Free

Brunch with Santa

 Sun, 14 Dec at 10:00 am 33 West St, Annapolis, MD, United States, Maryland 21401

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

 Sat, 13 Dec at 07:00 pm Maryland Hall for the Creative Arts

Brunch with Santa

 Sun, 14 Dec at 10:00 am Rams Head Roadhouse

Ballet Theatre of Maryland presents "The Nutcracker"

 Sat, 20 Dec at 07:00 pm Maryland Hall USD 47 to 72

A Very Merry Drag Brunch

Sun, 21 Dec at 12:30 pm Rams Head On Stage

Eastport Yacht Club Lights Parade

 Sat, 13 Dec at 06:00 pm Historic Downtown Annapolis

Eastport Yacht Club Boat Parade

 Sat, 13 Dec at 05:00 pm 110 Compromise St, Annapolis, MD 21401-1828, United States

Last Train Home

 Fri, 02 Jan at 08:00 pm Rams Head On Stage

Military Bowl: Pittsburgh Panthers vs. East Carolina Pirates

 Fri, 26 Dec at 07:00 pm Navy Marine Corps Memorial Stadium

Artist-led tour of Sacred Spaces with Jabari Jefferson

 Sat, 20 Dec at 12:00 pm Banneker-Douglass-Tubman Museum Free

Pressing Strings

 Sun, 28 Dec at 08:00 pm Rams Head On Stage

Siren's Call

 Fri, 26 Dec at 05:00 pm The Westin Annapolis Free

Holiday Virtual Charity Wine Dinner

 Sun, 14 Dec at 06:00 pm 36 West St, Annapolis, MD, United States, Maryland 21401

2026 Annapolis St. Patrick's Hooley!

 Sat, 07 Mar at 05:00 pm U.S. Naval Academy Alumni Association & Foundation USD 178

Annapolis Holiday Market 2025

 Sat, 13 Dec at 11:00 am St. John's College

A Fright Before Christmas - Ghost Story Dinner at Middleton Tavern

 Tue, 23 Dec at 06:30 pm Middleton Tavern

WINTER SOLSTICE CELEBRATION & SOUNDBATH

 Sun, 21 Dec at 04:30 pm Wellsview Cottage: Center for Holistic and Integrative Health Free

Six Times a Charm at Reclaimed of Annapolis

Sat, 13 Dec at 05:00 pm 129 Main Street Annapolis MD 21401

Danah Denice & Skribe @ Studio 333

 Fri, 19 Dec at 07:00 pm 333 Dubois Road, Annapolis, MD , 21401

Midnight Madness in Downtown Annapolis 2025

 Thu, 18 Dec at 04:00 pm Downtown Annapolis

Women in Business Networking Annapolis

 Fri, 20 Feb at 08:00 am Trendy Tides Boutique Free

Scorpion Rose

Sat, 20 Dec at 09:00 pm Blackwall Hitch - Annapolis

Jon McLaughlin and Friends: Home For The Holidays

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Happy Holidays Drag Brunch

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Women's Christmas Party

 Sat, 20 Dec at 10:00 am Crowne Plaza Annapolis, an IHG Hotel Free

Breathwork Amongst the Holiday Chaos with Gillian

 Tue, 16 Dec at 07:00 pm lululemon Free

Carbon Leaf: Carbon Leaf: 'I Want To Be Leaf' Tour 2025

 Sat, 13 Dec at 03:30 pm Rams Head On Stage

Eric Scott's Annual Holiday Celebration with very Special Guest Tony Denikos

 Mon, 15 Dec at 07:30 pm 49 West Coffeehouse, Winebar & Gallery

Shakey Graves

 Sat, 13 Dec at 07:00 pm Rams Head On Stage

Annual Kwanzaa Celebration

 Sat, 13 Dec at 10:00 am 84 Franklin St, Annapolis, MD, United States, Maryland 21401

Jimmie's Chicken Shack Holidaze Show

 Fri, 26 Dec at 08:00 pm Rams Head On Stage

Pressing Strings at Rams Head On Stage

 Sat, 27 Dec Rams Head On Stage

Restorative Yoga with Chelsea

 Tue, 16 Dec at 06:30 pm lululemon Free

Adult and Teen Isadora Duncan Dance Class with Kristen Kissik

 Fri, 02 Jan at 06:30 pm 4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409

Carbon Leaf: 'I Want To Be Leaf' Tour 2025

 Sat, 13 Dec at 08:30 pm Rams Head On Stage

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 21 Dec at 04:30 pm Maryland Hall USD 17 to 72

Paula Poundstone at Rams Head On Stage

 Fri, 19 Dec at 06:30 pm Rams Head On Stage

Breastfeeding Support Group in-person

 Thu, 18 Dec at 10:00 am AAMC Belcher Pavilion Free

Educational Dinner to Learn More About Hympavzi!

 Sun, 11 Jan at 04:00 pm Blackwall Hitch Free

Tides & Tunes

 Tue, 16 Dec at 05:00 pm The Westin Annapolis Free

Maternity Tour

 Sun, 04 Jan at 02:30 pm AAMC Clatanoff Pavilion Free

Happy Holidays Drag Brunch at Rams Head On Stage

 Sun, 21 Dec at 12:30 pm Rams Head On Stage

Jon McLaughlin at Rams Head On Stage

 Sun, 21 Dec at 07:30 pm Rams Head On Stage

Pressing Strings

 Fri, 26 Dec at 07:00 pm Rams Head On Stage

Holiday Pops at Maryland Hall

 Fri, 19 Dec at 07:30 pm Maryland Hall for the Creative Arts

Danny Burns Band: Southern Sky Album Release Tour

 Mon, 22 Dec at 08:00 pm Rams Head On Stage

Paint Night @ Starbucks [ANNAPOLIS HARBOUR CENTER]

 Sat, 20 Dec at 06:00 pm Starbucks USD 40

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 21 Dec at 01:00 pm Maryland Hall USD 17 to 72

Military Bowl

 Fri, 26 Dec Navy Marine Corps Memorial Stadium

Tides & Tunes

 Tue, 23 Dec at 05:00 pm The Westin Annapolis Free

Danny Burns Band

 Sun, 21 Dec at 07:00 pm Rams Head On Stage

The Chuck Brown Band (Dance Area!)

Sat, 31 Jan at 08:30 pm Rams Head On Stage

Witches of Maryland Pub Crawl

Sat, 13 Dec at 08:00 pm Downtown Anapolis

Chart House Prime - Frank Family Wine Dinner

 Thu, 22 Jan at 07:00 pm Chart House Prime USD 149

January Film Club - "Passion of Joan of Arc" (1928) w/ live music accomp

 Fri, 23 Jan at 06:00 pm AND Creative Studio USD 18

Songs of the Season - a holiday concert and sing-along

 Sun, 14 Dec at 03:00 pm Eastport United Methodist Church USD 0 to 12

Ballet Theatre of Maryland presents "Momentum: A Mixed Bill"

 Sat, 14 Feb at 07:00 pm Maryland Hall USD 39 to 64

Annapolis Color Run By Color Craze

 Sat, 09 May at 12:00 pm Downtown Annapolis

Jarrod Lawson concert at Rams Head On Stage

 Sat, 17 Jan at 08:00 pm Rams Head On Stage

The Honey Dew Drops in Annapolis, MD.

 Mon, 16 Feb at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 20

Live Arts Maryland Presents Broadway Favorites

 Fri, 20 Feb at 07:30 pm Maryland Hall USD 39

December Film Club - "The Exterminating Angel" (1962)

 Fri, 19 Dec at 06:00 pm AND Creative Studio USD 18

Coffee Pencils and Pastries

 Sat, 24 Jan at 10:00 am Tatte Bakery & Cafe | Annapolis USD 50

AMFM & Songbird Collective Present: A Tribute to Aretha Franklin (matinee)

Sun, 25 Jan at 12:30 pm Rams Head On Stage

Lights Parade Dinner Cruise with Ken's Creative Kitchen

 Sat, 13 Dec at 05:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Kashmir - The Led Zeppelin Experience

 Fri, 09 Jan at 07:00 pm Rams Head On Stage

Rams Head Presents The Bacon Brothers: Freestanding Tour - Maryland Hall - Annapolis, MD

 Thu, 22 Jan at 08:00 pm Maryland Hall

MOOD & ENERGY Clinic

 Sat, 13 Dec at 09:00 am 201A Ridgely Ave Free

solstice sound healing: echoes of the longest night w/ mia moon

 Fri, 19 Dec at 07:00 pm 48 Maryland Ave., Annapolis, MD, United States, Maryland 21403

Naptown Flea Vintage & Vinyl

 Sun, 01 Feb at 11:00 am 801 Chase St Free

Dave Matthews Tribute Band

 Sat, 24 Jan at 07:00 pm Rams Head On Stage

Ballet Theatre Of Maryland: The Nutcracker Tickets Annapolis MD Hall For The Creative Arts

 Sat, 13 Dec at 07:00 pm 801 Chase St, Annapolis, MD 21401-3530, United States

Dalton Connection Celebration & Networking Night

 Thu, 18 Dec at 06:30 pm Acqua al 2 - Annapolis Free

T Rose International Bridal Show Annapolis January 2026

 Sun, 04 Jan at 12:00 pm Crowne Plaza Annapolis, an IHG Hotel USD 18

The Young Fables in Annapolis, MD

 Fri, 20 Feb at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Ana Popovic: Dance To The Rhythm Tour (Matinee)

Sun, 11 Jan at 01:00 pm Rams Head On Stage

Ballet Theatre of Maryland presents "Momentum: A Mixed Bill"

 Fri, 13 Feb at 07:30 pm Maryland Hall USD 39 to 64

Discover Your Core Values with Rev. Sarah

 Sat, 24 Jan at 01:00 pm 4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409

Danah Denice Band at Rams Head On Stage

 Fri, 16 Jan at 08:00 pm Rams Head On Stage

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

 Sat, 20 Dec at 06:00 pm Charthouse Restaurant Annapolis

Jon McLaughlin & Friends: Home For The Holidays with T.3

 Sun, 21 Dec at 07:30 pm Rams Head On Stage

East of Maui Santa Paddle

 Sat, 13 Dec at 10:00 am Horn Point Street End Park

Here and Now: An Evening of Authentic Relating

 Thu, 29 Jan at 06:00 pm Unitarian Universalist Church of Annapolis USD 20

Vintage Vibe Finds private holiday shopping experience

 Sun, 14 Dec at 07:00 pm 40 Hudson St unit 107 USD 15

2nd Generation @ Dark Horse!

 Fri, 26 Dec at 08:00 pm 985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States

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

Sun, 15 Feb at 08:00 pm Rams Head On Stage

Siren's Call

 Fri, 19 Dec at 05:00 pm The Westin Annapolis Free
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