All Upcoming events

• Wed, 12 Nov, 2025 - 11:00 AM

  Strategic Tax Planning for Real Estate Professionals

  Frost Law Office
• 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
• Sat, 13 Dec, 2025 - 10:00 AM

  Annual Kwanzaa Celebration

  84 Franklin St, Annapolis, MD, United States, Maryland 21401
• Sun, 09 Nov, 2025 - 08:15 AM

  2025 Bay Bridge Run 10 K

  Bay Bridge
• Tue, 18 Nov, 2025 - 08:00 PM

  Naptown 2 NOLA Album Release Party with Papa Lebas & Gumbo Ya Ya

  Rams Head On Stage
• Sun, 29 Mar, 2026 - 08:00 PM

  Know Return & Fooling Ourselves: The Music of Kansas & STYX at Rams Head On Stage

  Rams Head On Stage
• Sun, 23 Nov, 2025 - 11:30 AM

  Autumn Harvest Brunch in Annapolis

  172 Green St
• Fri, 16 Jan, 2026 - 07:00 PM

  Jarrod Lawson

  Rams Head On Stage
• Wed, 03 Dec, 2025 - 07:00 PM

  A Peter White Christmas With Mindi Abair & Vincent Ingala

  Rams Head On Stage
• Sat, 09 May, 2026 - 12:00 PM

  Annapolis Color Run By Color Craze

  Downtown Annapolis
• Thu, 27 Nov, 2025 - 07:00 PM

  U2TOPIA

  Rams Head On Stage
• Wed, 18 Mar, 2026 - 08:00 PM

  Taj Farrant at Rams Head On Stage

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

  A Very Merry Drag Brunch

  Rams Head On Stage
• Sat, 22 Nov, 2025 - 07:00 PM

  Live Dead and Brothers - Grateful Dead and Allman Bros Tribute

  Rams Head On Stage
• Thu, 04 Dec, 2025 - 06:30 PM

  A Peter White Christmas w/ Mindi Abair & Vincent Ingala (6:30 PM)

  Rams Head On Stage
• Thu, 20 Nov, 2025 - 06:00 PM

  THE SAMPLES

  Annapolis Smokehouse And Tavern
• Sat, 06 Dec, 2025 - 07:00 PM

  Chris Isaak

  Maryland Hall For The Creative Arts
• Fri, 05 Dec, 2025 - 08:00 PM

  Pure Prairie League at Rams Head On Stage

  Rams Head On Stage
• Thu, 20 Nov, 2025 - 06:00 PM

  The Art Bar

  1851 McGuckian Street, Annapolis, MD, United States, Maryland 21401
• Thu, 18 Dec, 2025 - 07:00 PM

  Paula Poundstone

  Rams Head On Stage
• Sat, 20 Dec, 2025 - 12:00 PM

  A SQRRL! Holiday (Matinee)

  Rams Head On Stage
• Sat, 02 May, 2026 - 07:30 PM

  Live Arts Maryland Presents Timeless Brilliance

  Maryland Hall
• Tue, 11 Nov, 2025 - 07:30 PM

  Deadgrass at Live Arts Annapolis MD

  Live Arts MD Studio 801 Chase Street Annapolis, MD 21401
• Tue, 02 Dec, 2025 - 07:00 PM

  Evergreen Wreath Workshop

  1223 River Bay Road, Annapolis, MD, United States, Maryland 21409
• Sat, 06 Dec, 2025 - 08:00 PM

  Atlanta Rhythm Section at Rams Head On Stage

  Rams Head On Stage
• Sat, 06 Dec, 2025 - 09:00 AM

  The DeCesaris/Prout Jingle Bell Run/Walk

  Quiet Waters Park Annapolis, Md
• Tue, 11 Nov, 2025 - 05:00 PM

  Tides & Tunes

  The Westin Annapolis
• Sat, 15 Nov, 2025 - 06:00 PM

  Parking Sister Hazel

  Rams Head On Stage - Annapolis
• Wed, 03 Dec, 2025 - 08:00 PM

  The Empty Pockets at Rams Head On Stage

  Rams Head On Stage
• Sat, 27 Dec, 2025 - 11:00 AM

  Military Bowl at Navy Marine Corps Memorial Stadium

  Navy Marine Corps Memorial Stadium
• Sun, 07 Dec, 2025 - 01:00 PM

  Jeffrey Gaines, Sawyer Fredericks in Annapolis

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

  Jon McLaughlin and Friends: Home For The Holidays

  Rams Head On Stage
• Tue, 09 Dec, 2025 - 08:00 PM

  The Gilmour Project: Wish You Were Here

  Rams Head On Stage
• 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
• Tue, 11 Nov, 2025 - 04:00 PM

  F.A.C.T.O.R an Event Hosted by NextGen Collar

  The Westin Annapolis
• Sat, 20 Dec, 2025 - 07:00 PM

  Happy Holidays Drag Brunch

  Rams Head On Stage
• Sun, 07 Dec, 2025 - 03:00 PM

  Live Arts Maryland presents Christmas with Cantori

  Annapolis Mall
• Tue, 11 Nov, 2025 - 06:00 PM

  Fire & Flavor

  Annapolis Smokehouse and Tavern
• Wed, 03 Dec, 2025 - 05:30 PM

  Bubbles & Baubles

  Wrabyn Boutique
• Tue, 02 Dec, 2025 - 08:00 PM

  Son Little w/ Candi Jenkins

  Rams Head On Stage
• Sun, 14 Dec, 2025 - 01:00 PM

  Ballet Theatre of Maryland presents "The Nutcracker"

  Maryland Hall
• Sun, 09 Nov, 2025 - 07:00 PM

  The Sixties Show at Maryland Hall for the Creative Arts

  Maryland Hall for the Creative Arts
• Sun, 14 Dec, 2025 - 03:00 PM

  Valentines Day Flowers workshop

  47 Maryland Ave
• Thu, 04 Dec, 2025 - 06:30 PM

  A Peter White Christmas at Rams Head On Stage

  Rams Head On Stage
• Sat, 24 Jan, 2026 - 07:30 PM

  Maryland Hall Presents: WORLD PREMIERE: If I Die Before The Revolution

  801 Chase St, Annapolis, MD, United States, Maryland 21401
• Fri, 09 Jan, 2026 - 06:00 PM

  Maryland Yuletide Celebrations 2026

  DoubleTree by Hilton (Annapolis, MD)
• Fri, 13 Feb, 2026 - 08:00 PM

  Dan Tyminski Band at Rams Head On Stage

  Rams Head On Stage
• Sat, 27 Dec, 2025 - 08:00 PM

  Pressing Strings at Rams Head On Stage

  Rams Head On Stage
• Mon, 10 Nov, 2025 - 05:30 PM

  Paint & Poké @ BLOWFISH POKE HAWAIIAN GRILL [DOCK STREET]

  Blowfish Poké Hawaiian Grill
• Fri, 21 Nov, 2025 - 06:00 PM

  Special Olympics Md Anne Arundel County 4th Annual Bingo

  The Atreeum at Soaring Timbers
• Sun, 22 Mar, 2026 - 08:00 PM

  ZZ Ward at Rams Head On Stage

  Rams Head On Stage
• Wed, 26 Nov, 2025 - 09:00 PM

  Beersgiving

  33 West St, Annapolis, MD, United States, Maryland 21401
• Sun, 07 Dec, 2025 - 08:00 PM

  Chris Isaak at Maryland Hall for the Creative Arts

  Maryland Hall for the Creative Arts
• Thu, 04 Dec, 2025 - 06:00 PM

  Suzy & Shaun Duo in Annapolis

  The Annapolis Market House
• Fri, 14 Nov, 2025 - 07:00 PM

  Sister Hazel

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

  Danny Burns Band: Southern Sky Album Release Tour

  Rams Head On Stage
• Fri, 12 Dec Onwards

  Carbon Leaf

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

  Tab Benoit at Rams Head On Stage

  Rams Head On Stage
• Sun, 30 Nov, 2025 - 04:30 PM

  Grand Illumination

  Zachary's Jewelers
• Wed, 19 Nov, 2025 - 08:30 AM

  The WE C.A.R.E.™ Conference 2025

  801 Chase St
• Fri, 12 Dec, 2025 - 08:30 PM

  Carbon Leaf at Rams Head On Stage

  Rams Head On Stage
• Sat, 02 May, 2026 - 08:00 AM

  2026 Plant Sale

  1223 River Bay Road, Annapolis, MD, United States, Maryland 21409
• Mon, 09 Mar, 2026 - 08:00 PM

  Glen Phillips of Toad the Wet Sprocket at Rams Head On Stage

  Rams Head On Stage
• Sat, 07 Mar, 2026 - 06:00 PM

  Black Tie & Diamonds

  Graduate By Hilton Annapolis (Annapolis, MD)
• Wed, 12 Nov, 2025 - 02:00 PM

  FOOD FUNDRAISER: Always Ice Cream

  Always Ice Cream Company
• Sat, 22 Nov, 2025 - 05:00 PM

  NJIT Highlanders at Navy Midshipmen Mens Basketball

  Alumni Hall - Navy
• Fri, 20 Feb, 2026 - 07:30 PM

  Live Arts Maryland Presents Broadway Favorites

  Maryland Hall
• Sat, 29 Nov, 2025 - 06:00 PM

  Parking Navy Classic - Day 1

  Alumni Hall - Navy
• Sun, 16 Nov, 2025 - 06:00 PM

  Parking The Carole King & James Taylor Story

  Rams Head On Stage - Annapolis
• Sat, 27 Dec, 2025 - 04:00 PM

  Parking Military Bowl

  Navy-Marine Corps Memorial Stadium
• Sat, 06 Dec, 2025 - 06:00 PM

  Parking Laura Tsaggaris

  Rams Head On Stage - Annapolis
• Fri, 26 Dec, 2025 - 07:00 PM

  Pressing Strings

  Rams Head On Stage
• Sun, 11 Jan, 2026 - 01:00 PM

  Ana Popovic: Dance To The Rhythm Tour (Matinee)

  Rams Head On Stage
• Tue, 11 Nov, 2025 - 09:00 AM

  The Gathering

  Philip Merrill Environmental Center
• Sat, 17 Jan, 2026 - 08:00 PM

  Jarrod Lawson concert at Rams Head On Stage

  Rams Head On Stage
• Wed, 19 Nov, 2025 - 05:00 PM

  Fowler Fall Fundraiser

  Ram’s Head Down Bar 33 West Street, Annapolis Md
• Sat, 22 Nov, 2025 - 05:00 PM

  Parking NJIT Highlanders at Navy Midshipmen Mens Basketball

  Alumni Hall - Navy
• Sat, 15 Nov, 2025 - 08:00 PM

  The Carole King & James Taylor Story

  Rams Head On Stage - Annapolis
• Sat, 24 Jan, 2026 - 07:00 PM

  Dave Matthews Tribute Band

  Rams Head On Stage
• Tue, 02 Dec, 2025 - 06:00 PM

  2025-2026 Installation of Officers & Directors

  The Choptank - Annapolis
• Thu, 22 Jan Onwards

  Bruce In The U.S.A. - Bruce Springsteen Tribute

  Rams Head On Stage
• Sat, 24 Jan, 2026 - 07:00 PM

  The Dave Matthews Tribute Band

  Rams Head On Stage
• Sat, 07 Feb, 2026 - 10:00 AM

  Barbee's Memoirs Benefits Brunch at First Watch

  First Watch
• Mon, 17 Nov, 2025 - 08:00 PM

  Emma Nissen at Rams Head On Stage

  Rams Head On Stage
• Wed, 26 Nov, 2025 - 11:00 AM

  WED 11/26/25: Third Eye Holiday Homecoming / Games Giving Food Drive

  209 Chinquapin Round Rd, 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
• Fri, 27 Feb Onwards

  The Linda Ronstadt Experience

  Rams Head On Stage - Annapolis
• Wed, 12 Nov, 2025 - 07:00 PM

  Versed Fox

  35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401
• Wed, 31 Dec, 2025 - 09:00 PM

  Slugs & Special Guests - New Year’s Eve at Dark Horse!

  Dark Horse Annapolis
• Fri, 16 Jan, 2026 - 08:00 PM

  Danah Denice Band at Rams Head On Stage

  Rams Head On Stage
• Sun, 16 Nov, 2025 - 01:00 PM

  The Carole King and James Taylor Story at Rams Head On Stage

  Rams Head On Stage
• Mon, 16 Feb, 2026 - 07:30 PM

  The Honey Dew Drops at Annapolis, MD

  49 West St, Annapolis, MD 21401-2420, United States
• Sun, 08 Mar, 2026 - 05:00 PM

  The High Kings in Annapolis

  Rams Head On Stage
• Sun, 16 Nov, 2025 - 01:00 PM

  The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews (Matinee Added By Popular Demand!)

  Rams Head On Stage
• Sat, 08 Nov, 2025 - 06:00 PM

  DJ VER1TAS at Charthouse Prime Restaurant Annapolis

  Charthouse Restaurant Annapolis
• Sun, 09 Nov, 2025 - 08:00 PM

  Stan and Joe's Saloon West St Annapolis

  Stan and Joe's Saloon
• Thu, 26 Feb, 2026 - 09:00 AM

  Precision Agriculture Technology Conference 2026

  Crowne Plaza Annapolis by IHG
• Thu, 22 Jan, 2026 - 05:00 PM

  2026 Mountain Maryland PACE

  The Westin Annapolis
• Thu, 09 Apr, 2026 - 08:00 PM

  Penny and Sparrow in Annapolis

  Rams Head On Stage