All Upcoming events

• Fri, 05 Dec, 2025 - 08:00 PM

  Pure Prairie League in Annapolis

  Rams Head On Stage

  24+ Interested
• Sun, 07 Dec, 2025 - 11:00 AM

  Annapolis Chocolate Binge Festival

  53 West St, Annapolis, MD 21401-2420, United States

  703+ Interested
• Sun, 07 Dec, 2025 - 10:00 AM

  Nutcracker Tea 2025

  DoubleTree by Hilton Hotel Annapolis

  30+ Interested
• Sun, 07 Dec, 2025 - 08:00 PM

  Chris Isaak in Annapolis

  Maryland Hall
• Sun, 07 Dec, 2025 - 05:00 PM

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

  Latitude 38 Annapolis

  224+ Interested
• Wed, 31 Dec, 2025 - 08:00 PM

  New Year's Eve Annapolis Yacht Party

  1 Dock St, Annapolis, MD, United States, Maryland 21401

  11+ Interested
• Sat, 13 Dec, 2025 - 05:00 PM

  Annapolis Holiday of Lights Boat Parade

  680 Americana Dr

  USD 107
• Wed, 31 Dec, 2025 - 07:00 PM

  NYE at Charthouse Prime Restaurant Annapolis

  Charthouse Restaurant Annapolis

  4+ Interested
• Sun, 07 Dec, 2025 - 06:00 PM

  2025 Bike Doctor Holiday Lights Ride

  Safe Harbor Podickory Point

  40+ Interested
• Sun, 25 Jan, 2026 - 12:00 PM

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

  Graduate Annapolis

  303+ Interested
• Sun, 07 Dec, 2025 - 01:30 PM

  Storytime with the Grinch

  Discoveries: The Library at the Mall - Anne Arundel County Public Library

  Free
• Sun, 07 Dec, 2025 - 04:00 PM

  Family Karaoke Sunday - Powered by DJ KJ Ben

  Caliente Grill

  Free
• Sat, 06 Dec, 2025 - 09:30 AM

  Sold Out: Breakfast with Santa

  400 6th St, Annapolis, MD, United States, Maryland 21403

  12+ Interested
• Sat, 06 Dec, 2025 - 08:00 PM

  Atlanta Rhythm Section in Annapolis

  Rams Head On Stage
• Fri, 06 Feb, 2026 - 06:30 PM

  Get Closer: Couples Tantra Workshop

  groundswell yoga annapolis

  USD 232
• Sat, 13 Dec, 2025 - 05:00 PM

  Eastport Yacht Club Boat Parade

  110 Compromise St, Annapolis, MD 21401-1828, United States

  1000+ Interested
• Sun, 14 Dec, 2025 - 10:00 AM

  Brunch with Santa

  33 West St, Annapolis, MD, United States, Maryland 21401

  20+ Interested
• Wed, 31 Dec, 2025 - 10:00 PM

  New Years Eve Cruise 2026

  680 Americana Dr

  USD 107
• Wed, 10 Dec, 2025 - 06:00 PM

  Paint Night @ NEO PIZZA - Annapolis

  Neo Pizza & Taphouse

  USD 40
• Fri, 05 Dec, 2025 - 07:00 PM

  illuminate your shadows: a women's meditation circle

  48 Maryland Ave., Annapolis, MD, United States, Maryland 21403
• Fri, 05 Dec, 2025 - 07:30 PM

  Full Moon Celebration - December

  Unitarian Universalist Church of Annapolis

  30+ Interested
• Sat, 13 Dec, 2025 - 08:00 PM

  Witches of Maryland Pub Crawl

  Downtown Anapolis
• Sat, 06 Dec, 2025 - 09:30 AM

  41st Annual Broadneck Craft Bazaar

  1265 Green Holly Dr, Annapolis, MD

  2136+ Interested
• Fri, 12 Dec, 2025 - 06:00 PM

  Mystery Art Making: Trash to Treasure

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Fri, 05 Dec, 2025 - 07:00 PM

  The Fright Before Christmas - Pub Crawl

  Annapolis Ghost Tours & Crawls

  8+ Interested
• Fri, 05 Dec, 2025 - 08:00 PM

  Hidden History Pub Crawl

  16 Church Cir, Annapolis, MD 21401-1927, United States
• Thu, 11 Dec, 2025 - 07:30 PM

  U.S. Naval Academy Band Holiday by the Bay Concert

  Naval Academy Chapel
• Fri, 05 Dec, 2025 - 07:00 PM

  Holiday Candlelight Stroll

  188 Main St, Annapolis, MD 21401-2008, United States
• Sun, 07 Dec, 2025 - 07:00 PM

  Tab Benoit: I Hear Thunder Tour w/ Jesse Dayton

  Rams Head On Stage

  52+ Interested
• Thu, 11 Dec, 2025 - 08:00 PM

  Peter Mayer: A Stars and Promises Christmas 2025

  Rams Head On Stage

  105+ Interested
• Sun, 07 Dec, 2025 - 08:00 PM

  Rams Head Presents Chris Isaak - Annapolis, MD

  Maryland Hall

  37+ Interested
• Fri, 12 Dec, 2025 - 07:30 PM

  Jeff Muller & Friends present Traveling Traditions

  49 West Coffeehouse, Winebar & Gallery
• Sat, 07 Mar, 2026 - 05:00 PM

  2026 Annapolis St. Patrick's Hooley!

  U.S. Naval Academy Alumni Association & Foundation

  USD 178
• Sat, 13 Dec, 2025 - 07:00 PM

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

  801 Chase St, Annapolis, MD 21401-3530, United States
• Fri, 05 Dec, 2025 - 05:30 PM

  Block Printing: Holiday Tags and Bags

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Sun, 14 Dec, 2025 - 06:00 PM

  Holiday Virtual Charity Wine Dinner

  36 West St, Annapolis, MD, United States, Maryland 21401

  4+ Interested
• Fri, 05 Dec, 2025 - 06:00 PM

  Holiday-Themed Turkish Marbling: Ornaments, Cards, Gift Tags

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Sun, 07 Dec, 2025 - 05:00 PM

  The Moonshiner's Ball 2025

  Latitude 38 Annapolis
• Thu, 11 Dec, 2025 - 04:00 PM

  Midnight Madness in Downtown Annapolis 2025

  Downtown Annapolis
• Sat, 06 Dec, 2025 - 08:00 PM

  Atlanta Rhythm Section at Rams Head On Stage

  Rams Head On Stage
• Sat, 06 Dec, 2025 - 07:00 PM

  Jeffrey Gaines & Sawyer Fredericks

  Rams Head On Stage
• Sat, 10 Jan, 2026 - 06:00 PM

  Fireside Revelry: A Colonial Twelfth Night Concert

  19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401
• Sat, 06 Dec, 2025 - 04:00 PM

  Author Event: Brian Trapp

  25 Maryland Ave, Annapolis, MD 21401-1627, United States
• Sat, 13 Dec, 2025 - 06:00 PM

  Eastport Yacht Club Lights Parade

  Historic Downtown Annapolis

  4598+ Interested
• Sat, 13 Dec, 2025 - 11:00 AM

  Annapolis Holiday Market 2025

  St. John's College

  536+ Interested
• Fri, 19 Dec, 2025 - 05:30 PM

  Family Art Night: Holiday Cards

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Sat, 06 Dec, 2025 - 09:00 PM

  Live Music with Ghosts on the Wall

  Rams Head Roadhouse
• Sat, 06 Dec, 2025 - 03:00 PM

  Special Historic Holiday Tour

  188 Main St, Annapolis, MD 21401-2008, United States
• Sat, 06 Dec, 2025 - 09:45 PM

  Honey Sol at Stan & Joe’s

  Stan and Joe's Saloon
• Fri, 19 Dec, 2025 - 06:30 PM

  Living Nativity

  1740 Forest Dr, Annapolis, MD
• Sun, 11 Jan, 2026 - 08:00 PM

  Dead Letter Office: A Tribute of R.E.M

  Rams Head On Stage
• Sat, 06 Dec, 2025 - 07:00 PM

  Chris Isaak

  Maryland Hall For The Creative Arts
• Mon, 15 Dec, 2025 - 07:30 PM

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

  49 West Coffeehouse, Winebar & Gallery
• Sun, 14 Dec, 2025 - 05:00 PM

  FERS/CSRS Benefits Workshop Annapolis - 12/14/25

  DoubleTree by Hilton Hotel Annapolis
• Sat, 20 Dec, 2025 - 08:00 PM

  Holiday Improv Comedy Show - Annapolis Maryland

  ArtFarm

  Newly Added

  |

  USD 10
• Sat, 06 Dec, 2025 - 07:00 PM

  Tab Benoit

  Rams Head On Stage
• Fri, 05 Dec, 2025 - 08:00 PM

  Pure Prairie League at Rams Head On Stage

  Rams Head On Stage
• Sat, 13 Dec, 2025 - 07:00 PM

  Shakey Graves

  Rams Head On Stage
• Fri, 05 Dec, 2025 - 12:00 PM

  Jolly Express Cruise

  1 Dock St, Annapolis, MD, United States, Maryland 21401
• Sat, 20 Dec, 2025 - 07:00 PM

  Happy Holidays Drag Brunch

  Rams Head On Stage
• Wed, 31 Dec, 2025 - 08:00 PM

  The Choptank's New Years Eve Party

  The Choptank - Annapolis

  USD 143
• Sat, 13 Dec, 2025 - 10:00 AM

  Annual Kwanzaa Celebration

  84 Franklin St, Annapolis, MD, United States, Maryland 21401

  36+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Transform Your Photos: Photo Editing & File Organizing Workshop

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Sat, 13 Dec, 2025 - 03:30 PM

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

  Rams Head On Stage

  49+ Interested
• Sun, 21 Dec, 2025 - 12:30 PM

  A Very Merry Drag Brunch

  Rams Head On Stage

  279+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Colonial Annapolis & Maryland State House Walking Tour

  1 Dock St, Annapolis, MD, United States, Maryland 21401
• Sat, 13 Dec, 2025 - 08:30 PM

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

  Rams Head On Stage

  30+ Interested
• Wed, 17 Dec, 2025 - 08:00 PM

  Jay Hurtt VI w/ Skribe

  Rams Head On Stage
• Sat, 20 Dec, 2025 - 07:00 PM

  Jon McLaughlin and Friends: Home For The Holidays

  Rams Head On Stage
• Thu, 11 Dec, 2025 - 05:30 PM

  Certification Celebration

  ArtFarm Annapolis
• Thu, 11 Dec, 2025 - 07:30 PM

  Ugly Sweater Ride

  Acton Cove
• Sat, 06 Dec, 2025 - 06:00 PM

  SOD-O Holiday Party

  Acqua al 2 - Annapolis

  Free
• Tue, 09 Dec, 2025 - 08:00 PM

  The Gilmour Project: Wish You Were Here

  Rams Head On Stage

  17+ Interested
• Fri, 26 Dec, 2025 - 08:00 PM

  Jimmie's Chicken Shack Holidaze Show

  Rams Head On Stage

  186+ Interested
• Sat, 20 Dec, 2025 - 12:00 PM

  A SQRRL! Holiday (Matinee)

  Rams Head On Stage
• Sun, 07 Dec, 2025 - 07:00 PM

  Tab Benoit at Rams Head On Stage

  Rams Head On Stage
• Sun, 07 Dec, 2025 - 08:00 PM

  Chris Isaak at Maryland Hall for the Creative Arts

  Maryland Hall for the Creative Arts
• Sun, 21 Dec, 2025 - 05:00 PM

  A Longest Night Service

  Eastport United Methodist Church
• Sat, 13 Dec, 2025 - 11:00 AM

  Pet Photos With Santa

  Annapolis Pearl Gallery
• Fri, 05 Dec, 2025 - 05:00 PM

  LIVE MUSIC: One Step Down

  Rams Head Tavern Annapolis
• Tue, 09 Dec, 2025 - 05:00 PM

  Tides & Tunes

  The Westin Annapolis

  Free
• Fri, 26 Dec, 2025 - 09:00 PM

  LIVE MUSIC with Enslow

  Blackwall Hitch - Annapolis
• Fri, 05 Dec, 2025 - 07:30 PM

  Live Arts Maryland presents Bluegrass Nutcracker

  Annapolis Mall

  USD 34
• Sat, 27 Dec, 2025 - 08:00 PM

  Choptank Annapolis

  The Choptank - Annapolis
• Sun, 14 Dec, 2025 - 12:00 PM

  Mono printed Wrapping Paper Workshop

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Sun, 25 Jan, 2026 - 06:00 PM

  January Virtual Charity Wine Dinner

  36 West St, Annapolis, MD, United States, Maryland 21401
• Wed, 31 Dec, 2025 - 08:45 PM

  New Year's Eve at Acqua al 2

  Acqua al 2 - Annapolis, Main Street, Annapolis, MD, USA

  USD 150
• Sun, 21 Dec, 2025 - 04:30 PM

  Candlelight: Christmas Carols on Strings | Annapolis

  Annapolis Waterfront Hotel
• Sat, 06 Dec, 2025 - 06:00 PM

  2025 FRA 24 Holiday Party

  Fleet Reserve Club Of Annapolis

  USD 66
• Sat, 13 Dec, 2025 - 02:00 PM

  Holiday Appreciation Event hosted by Century 21 New Millennium

  1730 West St, Annapolis, MD
• Sun, 07 Dec, 2025 - 09:30 AM

  Sunday Morning Yoga in the Gallery

  AND Creative
• Sat, 06 Dec, 2025 - 07:30 PM

  Scandalous Annapolis Tour

  Watermark Tours Charters Cruises
• Fri, 05 Dec, 2025 - 06:30 PM

  Be Still and Know: A Journey Into Sound & Soul

  Unity by the Bay

  USD 39
• Fri, 05 Dec, 2025 - 06:30 PM

  Be Still & Know

  Unity by the Bay (Maryland)
• Sat, 20 Dec, 2025 - 06:00 PM

  Paint Night @ Starbucks [ANNAPOLIS HARBOUR CENTER]

  Starbucks

  USD 40
• Thu, 18 Dec, 2025 - 10:00 AM

  Breastfeeding Support Group in-person

  AAMC Belcher Pavilion

  Free
• Sat, 09 May, 2026 - 12:00 PM

  Annapolis Color Run By Color Craze

  Downtown Annapolis
• Sun, 08 Feb, 2026 - 08:00 PM

  Dan Haas: reHAASh reTROSPECTIve

  Rams Head On Stage
• Sun, 14 Dec, 2025 - 08:00 AM

  Heroes Holiday Market

  1 Riverview Avenue, Annapolis, MD

  69+ Interested