All Upcoming events

• Sat, 13 Dec, 2025 - 05:00 PM

  Annapolis Holiday of Lights Boat Parade

  680 Americana Dr

  6+ Interested

  |

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

  NYE at Charthouse Prime Restaurant Annapolis

  Charthouse Restaurant Annapolis

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

  New Year's Eve Annapolis Yacht Party

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

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

  The Choptank's New Years Eve Party

  The Choptank - Annapolis

  USD 143
• 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, 25 Jan, 2026 - 12:00 PM

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

  Graduate Annapolis

  303+ Interested
• Wed, 10 Dec, 2025 - 06:00 PM

  Paint Night @ NEO PIZZA - Annapolis

  Neo Pizza & Taphouse

  USD 40
• Wed, 31 Dec, 2025 - 10:00 PM

  New Years Eve Cruise 2026

  680 Americana Dr

  USD 107
• Fri, 06 Feb, 2026 - 06:30 PM

  Get Closer: Couples Tantra Workshop

  groundswell yoga annapolis

  USD 232
• Sun, 14 Dec, 2025 - 07:00 PM

  An Annapolis Christmas

  Rams Head On Stage
• Sun, 14 Dec, 2025 - 10:00 AM

  Brunch with Santa

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

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

  Eastport Yacht Club Boat Parade

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

  1000+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

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

  Maryland Hall for the Creative Arts
• Sun, 21 Dec, 2025 - 12:30 PM

  A Very Merry Drag Brunch

  Rams Head On Stage

  286+ Interested
• Trending
  Sat, 20 Dec, 2025 - 08:00 PM

  Holiday Improv Comedy Show - Annapolis Maryland

  ArtFarm

  Newly Added

  |

  USD 10
• Thu, 11 Dec, 2025 - 08:00 PM

  Peter Mayer: A Stars and Promises Christmas 2025

  Rams Head On Stage

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

  Artist-led tour of Sacred Spaces with Jabari Jefferson

  Banneker-Douglass-Tubman Museum

  Free
• Sat, 13 Dec, 2025 - 06:00 PM

  Eastport Yacht Club Lights Parade

  Historic Downtown Annapolis

  4768+ Interested
• Sun, 14 Dec, 2025 - 06:00 PM

  Holiday Virtual Charity Wine Dinner

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

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

  Lights Parade Dinner Cruise with Ken's Creative Kitchen

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

  29+ Interested
• Sat, 07 Mar, 2026 - 05:00 PM

  2026 Annapolis St. Patrick's Hooley!

  U.S. Naval Academy Alumni Association & Foundation

  USD 178
• Sun, 21 Dec, 2025 - 04:30 PM

  WINTER SOLSTICE CELEBRATION & SOUNDBATH

  Wellsview Cottage: Center for Holistic and Integrative Health

  Free
• Thu, 18 Dec, 2025 - 06:30 PM

  Dalton Connection Celebration & Networking Night

  Acqua al 2 - Annapolis

  Free
• Sat, 13 Dec, 2025 - 05:00 PM

  Six Times a Charm at Reclaimed of Annapolis

  129 Main Street Annapolis MD 21401
• Sat, 13 Dec, 2025 - 11:00 AM

  Annapolis Holiday Market 2025

  St. John's College

  1002+ Interested
• Sat, 10 Jan, 2026 - 06:00 PM

  Fireside Revelry: A Colonial Twelfth Night Concert

  19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

  13+ Interested
• Fri, 20 Feb, 2026 - 08:00 AM

  Women in Business Networking Annapolis

  Trendy Tides Boutique

  Free
• Sat, 13 Dec, 2025 - 11:00 AM

  2025 Santa Speedo Run

  O'Brien's Oyster Bar & Seafood Tavern

  408+ Interested
• Sat, 20 Dec, 2025 - 10:00 AM

  Women's Christmas Party

  Crowne Plaza Annapolis, an IHG Hotel

  Free
• Sat, 20 Dec, 2025 - 12:00 PM

  A SQRRL! Holiday at Rams Head On Stage

  Rams Head On Stage
• Sat, 20 Dec, 2025 - 09:00 PM

  Scorpion Rose

  Blackwall Hitch - Annapolis

  23+ Interested
• Thu, 11 Dec, 2025 - 07:30 PM

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

  Naval Academy Chapel

  144+ Interested
• Sat, 13 Dec, 2025 - 03:30 PM

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

  Rams Head On Stage

  49+ Interested
• Sat, 20 Dec, 2025 - 07:00 PM

  Jon McLaughlin and Friends: Home For The Holidays

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

  Happy Holidays Drag Brunch

  Rams Head On Stage
• Mon, 15 Dec, 2025 - 07:30 PM

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

  49 West Coffeehouse, Winebar & Gallery
• Fri, 19 Dec, 2025 - 06:00 PM

  Indian Creek Annual Holiday Gathering

  Pearl Restaurant

  5+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

  Shakey Graves

  Rams Head On Stage
• Sat, 13 Dec, 2025 - 10:00 AM

  Annual Kwanzaa Celebration

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

  36+ Interested
• Tue, 03 Feb, 2026 - 08:00 PM

  G Love and Special Sauce at Rams Head On Stage

  Rams Head On Stage
• Fri, 26 Dec, 2025 - 08:00 PM

  Jimmie's Chicken Shack Holidaze Show

  Rams Head On Stage

  186+ Interested
• Fri, 02 Jan, 2026 - 06:30 PM

  Adult and Teen Isadora Duncan Dance Class with Kristen Kissik

  4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409
• Sat, 13 Dec, 2025 - 08:30 PM

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

  Rams Head On Stage

  32+ Interested
• Sat, 27 Dec, 2025 - 08:00 PM

  Pressing Strings at Rams Head On Stage

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

  Shakey Graves, Clover County in Annapolis

  Rams Head On Stage
• Sun, 21 Dec, 2025 - 12:30 PM

  Happy Holidays Drag Brunch at Rams Head On Stage

  Rams Head On Stage
• Thu, 18 Dec, 2025 - 10:00 AM

  Breastfeeding Support Group in-person

  AAMC Belcher Pavilion

  Free
• Fri, 19 Dec, 2025 - 06:30 PM

  Paula Poundstone at Rams Head On Stage

  Rams Head On Stage
• Sun, 21 Dec, 2025 - 07:30 PM

  Jon McLaughlin at Rams Head On Stage

  Rams Head On Stage
• Mon, 22 Dec, 2025 - 08:00 PM

  Danny Burns Band: Southern Sky Album Release Tour

  Rams Head On Stage

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

  Witches of Maryland Pub Crawl

  Downtown Anapolis
• Fri, 26 Dec, 2025 - 07:00 PM

  Pressing Strings

  Rams Head On Stage
• Sat, 20 Dec, 2025 - 06:00 PM

  Paint Night @ Starbucks [ANNAPOLIS HARBOUR CENTER]

  Starbucks

  USD 40
• Sat, 09 May, 2026 - 12:00 PM

  Annapolis Color Run By Color Craze

  Downtown Annapolis
• Fri, 19 Dec, 2025 - 07:30 PM

  Holiday Pops at Maryland Hall

  Maryland Hall for the Creative Arts

  20+ 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
• Thu, 11 Dec, 2025 - 06:30 PM

  ¿Cómo andas con el amor hacia ti misma?

  2158 Renard Ct

  Free
• Sat, 31 Jan, 2026 - 08:30 PM

  The Chuck Brown Band (Dance Area!)

  Rams Head On Stage

  141+ Interested
• Sun, 14 Dec, 2025 - 04:00 PM

  Ave Maria A Christmas Concert

  1120 Spa Road, Annapolis, MD, United States, Maryland 21403
• Fri, 13 Feb, 2026 - 07:30 PM

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

  Maryland Hall

  USD 39
• Sun, 21 Dec, 2025 - 07:00 PM

  Danny Burns Band

  Rams Head On Stage
• Sat, 10 Jan, 2026 - 08:30 PM

  Ram's Head on Stage

  Rams Head On Stage

  17+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Jarrod Lawson concert at Rams Head On Stage

  Rams Head On Stage
• Fri, 12 Dec, 2025 - 07:30 PM

  Jeff Muller & Friends present Traveling Traditions

  49 West Coffeehouse, Winebar & Gallery

  40+ Interested
• Fri, 20 Feb, 2026 - 07:30 PM

  Live Arts Maryland Presents Broadway Favorites

  Maryland Hall

  USD 39
• Fri, 12 Dec, 2025 - 06:00 PM

  Holiday Herb Wreath Workshop

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Wed, 10 Dec, 2025 - 06:00 PM

  Michael K. Solo at Middleton Tavern

  Middleton Tavern
• Fri, 19 Dec, 2025 - 06:00 PM

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

  AND Creative Studio

  USD 18
• Sat, 13 Dec, 2025 - 09:00 AM

  MOOD & ENERGY Clinic

  201A Ridgely Ave

  Free
• Sat, 13 Dec, 2025 - 09:30 AM

  Speaking in Sign - for Girl Scout Brownies and Juniors

  25 Silopanna Rd, Annapolis, MD, United States, Maryland 21403
• Sat, 27 Dec, 2025 - 11:00 AM

  Military Bowl - Pittsburgh vs East Carolina at Navy Marine Corps Memorial Stadium

  Navy Marine Corps Memorial Stadium
• Sat, 19 Sep, 2026 - 10:00 AM

  BAYGRASS 2026: Annapolis Baygrass Music Festival 9/19-20

  1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

  516+ Interested
• Fri, 09 Jan, 2026 - 07:00 PM

  Kashmir - The Led Zeppelin Experience

  Rams Head On Stage
• 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
• Thu, 22 Jan, 2026 - 08:00 PM

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

  Maryland Hall

  137+ Interested
• Thu, 11 Dec, 2025 - 04:00 PM

  Midnight Madness in Downtown Annapolis 2025

  Downtown Annapolis

  372+ Interested
• Sat, 24 Jan, 2026 - 01:00 PM

  Discover Your Core Values with Rev. Sarah

  4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409
• Sun, 01 Feb, 2026 - 11:00 AM

  Naptown Flea Vintage & Vinyl

  801 Chase St

  Free
• Fri, 19 Dec, 2025 - 07:00 PM

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

  48 Maryland Ave., Annapolis, MD, United States, Maryland 21403

  7+ Interested
• Thu, 11 Dec, 2025 - 06:00 PM

  DJ VER1TAS at Charthouse Prime Restaurant Annapolis

  Charthouse Restaurant Annapolis
• Fri, 20 Feb, 2026 - 07:30 PM

  The Young Fables in Annapolis, MD

  49 West Coffeehouse, Winebar & Gallery

  USD 23
• Sun, 21 Dec, 2025 - 07:30 PM

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

  Rams Head On Stage

  30+ Interested
• Sun, 11 Jan, 2026 - 01:00 PM

  Ana Popovic: Dance To The Rhythm Tour (Matinee)

  Rams Head On Stage

  38+ Interested
• Sun, 14 Dec, 2025 - 07:00 PM

  Vintage Vibe Finds private holiday shopping experience

  40 Hudson St unit 107

  USD 15
• Sat, 24 Jan, 2026 - 07:00 PM

  Dave Matthews Tribute Band

  Rams Head On Stage
• Sat, 13 Dec, 2025 - 10:00 AM

  East of Maui Santa Paddle

  Horn Point Street End Park

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

  2nd Generation @ Dark Horse!

  985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States
• Fri, 16 Jan, 2026 - 08:00 PM

  Danah Denice Band at Rams Head On Stage

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

  Siren's Call

  The Westin Annapolis

  Free
• Fri, 19 Dec, 2025 - 05:30 PM

  Family Art Night: Holiday Cards

  111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401
• Sun, 15 Feb, 2026 - 08:00 PM

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

  Rams Head On Stage

  789+ Interested
• Sat, 10 Jan, 2026 - 01:00 PM

  Sacred Triptych Workshop with Rev. Sarah Phillips and Lolly Jefferson

  4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409
• Thu, 18 Dec, 2025 - 07:00 PM

  Paula Poundstone

  Rams Head On Stage
• Thu, 22 Jan, 2026 - 05:00 PM

  2026 Mountain Maryland PACE

  The Westin Annapolis

  USD 189
• Sat, 13 Dec, 2025 - 09:00 PM

  LIVE MUSIC with Rick & The Revolving Doors

  Blackwall Hitch - Annapolis
• Fri, 13 Nov, 2026 - 07:00 PM

  Come Out and Play in DMV/Annapolis 2026

  210 Holiday Ct

  USD 18
• Fri, 12 Dec, 2025 - 09:45 PM

  R&R Returns to Rock Stan & Joe’s Saloon in Annapolis

  Stan and Joe's Saloon
• Thu, 11 Dec Onwards

  Carbon Leaf

  Rams Head On Stage
• Fri, 16 Jan, 2026 - 07:00 PM

  Jarrod Lawson

  Rams Head On Stage