Upcoming Annapolis Events

Name: Fall Festival on Maryland Ave
Start: 2025-10-19
End: 2025-10-19
Location: Maryland Avenue, Annapolis

Check out what's happening all around Annapolis, MD

Sister Hazel

Fri, 14 Nov at 07:00 pm Rams Head On Stage

Spyro Gyra

Wed, 04 Mar at 07:00 pm Rams Head On Stage

Pure Prairie League in Annapolis

Fri, 05 Dec at 08:00 pm Rams Head On Stage

Black Tie & Diamonds

Sat, 07 Mar at 06:00 pm Graduate By Hilton Annapolis (Annapolis, MD)

Emma Nissen at Rams Head On Stage

Mon, 17 Nov at 08:00 pm Rams Head On Stage

Tribute Night: Sly Stone & Earth, Wind & Fire

Sun, 19 Oct at 08:00 pm Rams Head On Stage

Scandalous Annapolis Tour

Sat, 01 Nov at 07:30 pm Watermark Tours Charters Cruises

Winemaker Dinner with Louisa Rose

Tue, 21 Oct at 06:30 pm 36 West St, Annapolis, MD, United States, Maryland 21401

Ballet Theatre of Maryland presents "Giselle"

Sun, 19 Oct at 02:00 pm Maryland Hall USD 39 to 64

Live Arts Maryland Presents Broadway Favorites

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

The WE C.A.R.E.™ Conference 2025

Wed, 19 Nov at 08:30 am 801 Chase St Free

Unity Rhythm and Drum Circle

Mon, 27 Oct at 06:30 pm Unity by the Bay (Maryland)

Ballet Theatre of Maryland presents "The Nutcracker"

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

Annapolis Jazz & Roots Festival "Art Music & the Muse" Artist talk - Jabari and JC Jefferson

Sat, 08 Nov at 01:00 pm Banneker-Douglass-Tubman Museum

Undead Mile Run – Annapolis, MD

Sat, 25 Oct at 08:00 pm Annapolis, Annapolis, Maryland

Najee in Annapolis

Sun, 09 Nov at 07:30 pm Rams Head On Stage

Pure Prairie League in Annapolis

Fri, 05 Dec at 08:00 pm Rams Head On Stage

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Thu, 04 Dec at 06:30 pm Rams Head On Stage

Keb' Mo' in Annapolis

Fri, 21 Nov at 08:00 pm Maryland Hall

Najee in Annapolis

Sun, 09 Nov at 04:30 pm Rams Head On Stage

Richard Thompson in Annapolis

Sun, 02 Nov at 07:30 pm St. John's College - Francis Scott Key Auditorium

Fall Festival on Maryland Avenue

Sun, 19 Oct at 10:00 am Maryland Ave at State Cir, Annapolis, MD, United States, Maryland 21401

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Thu, 04 Dec at 06:30 pm Rams Head On Stage

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Thu, 04 Dec at 09:30 pm Rams Head On Stage

2025 Shore Party

Sat, 01 Nov at 05:00 pm Safe Harbor Annapolis

Annapolis Halloween Rooftop Party : Haunted Heights

Fri, 31 Oct at 08:00 pm Metropolitan Kitchen & Lounge Free

Dancing Night at Caliente Grill - Bachata Class & Social Dance

Fri, 24 Oct at 08:00 pm Caliente Grill Free

Tall Tall Trees & Christopher Paul Stelling

Fri, 24 Oct at 07:00 pm Rams Head On Stage

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

Sun, 07 Dec at 05:00 pm Latitude 38 Annapolis

Thomas Dolby - The Iconic 80s at Rams Head On Stage

Fri, 24 Oct at 08:00 pm Rams Head On Stage

Atlanta Rhythm Section in Annapolis

Sat, 06 Dec at 08:00 pm Rams Head On Stage

Love Yourselfie with Girl Scouts

Mon, 20 Oct at 06:15 pm Eastport-Annapolis Neck Library - Anne Arundel County Public Library Free

Pressing Strings

Sat, 27 Dec Rams Head On Stage

Matthew Clark: An Evening of Songs and Stories

Sat, 01 Nov at 07:00 pm Downtown Hope USD 10

Richard Thompson

Sat, 01 Nov at 07:00 pm Francis Scott Key Auditorium

A2B Offshore Racing Safety Seminar

Sat, 15 Nov at 09:00 am 317 First Street , Annapolis, MD, United States, Maryland 21403

Crack the Sky at Rams Head On Stage

Fri, 31 Oct at 08:00 pm Rams Head On Stage

Siren's Call

Fri, 24 Oct at 05:00 pm The Westin Annapolis Free

Wishbone Ash: Wishlist Tour

Sat, 08 Nov at 08:00 pm Rams Head On Stage

Navy Midshipmen Tailgate Party

Sat, 25 Oct at 01:30 pm The Westin Annapolis Free

Chris Isaak in Annapolis

Sun, 07 Dec at 08:00 pm Maryland Hall

Intuitive Mandala Paint Night with Christalene ✨

Sat, 01 Nov at 06:00 pm Blush Hair Salon & Head Spa, 2431 Solomons Island Rd #102, Annapolis, MD 21401, USA

Marshall Crenshaw: 40+ Years in Showbiz

Fri, 14 Nov at 08:00 pm Rams Head On Stage

Siren's Call

Fri, 31 Oct at 05:00 pm The Westin Annapolis Free

Come Out and Play with Naleighna Kai and the Tribe

Fri, 31 Oct at 07:00 pm 210 Holiday Ct USD 0 to 109

Nutcracker Tea 2025

Sun, 07 Dec at 10:00 am DoubleTree by Hilton Hotel Annapolis

Eli Lev at Unity by the Bay Church

Fri, 07 Nov at 07:00 pm Unity by the Bay (Maryland)

Macy Gray at Rams Head On Stage

Sun, 02 Nov at 08:30 pm Rams Head On Stage

Natalie Merchant

Sat, 22 Nov at 07:00 pm Maryland Hall For The Creative Arts

Paint Night @ Starbucks [ANNAPOLIS HARBOUR CENTER]

Sun, 26 Oct at 06:00 pm Starbucks USD 40

Rams Head Presents Natalie Merchant w/ Erik Della Penna: Autumn Acoustic Tour - Maryland Hall

Sun, 23 Nov at 07:30 pm Maryland Hall

Los Straitjackets at Rams Head On Stage

Sat, 14 Mar at 08:00 pm Rams Head On Stage

Siren's Call

Fri, 07 Nov at 05:00 pm The Westin Annapolis Free

The Brit Pack: The Ultimate British Music Experience

Sat, 22 Nov at 08:00 pm Rams Head On Stage

Will Hoge

Sat, 15 Nov at 07:00 pm Rams Head On Stage

GA-20 and Black Joe Lewis & The Honeybears

Thu, 23 Oct at 08:00 pm Rams Head On Stage

Tribute Show for John “Jumaane” Noel

Sat, 08 Nov at 08:00 pm Metropolitan Kitchen & Lounge USD 0 to 15

Keb Mo at Maryland Hall for the Creative Arts

Fri, 21 Nov at 08:00 pm Maryland Hall for the Creative Arts

Danah Denice Band at Rams Head On Stage

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

GA20 at Rams Head On Stage

Thu, 23 Oct at 08:00 pm Rams Head On Stage

Siren's Call

Fri, 14 Nov at 05:00 pm The Westin Annapolis Free

Live Dead and Brothers - Grateful Dead and Allman Bros Tribute

Sat, 22 Nov at 07:00 pm Rams Head On Stage

Navy Midshipmen Tailgate Party

Sat, 15 Nov at 10:00 am The Westin Annapolis Free

Collector's Choice 2025

Sun, 19 Oct at 06:00 pm Volvo Cars Annapolis

Ketch Secor

Sun, 02 Nov at 07:00 pm Rams Head On Stage

Maternity Tour

Sat, 08 Nov at 02:30 pm AAMC Clatanoff Pavilion Free

Siren's Call

Fri, 21 Nov at 05:00 pm The Westin Annapolis Free

The Doug Segree Band at 49 West

Mon, 17 Nov at 07:30 pm 49 West St, Annapolis, MD 21401-2420, United States

Will Hoge w/ July Moon

Sun, 16 Nov at 08:00 pm Rams Head On Stage

Tall Tall Trees at Rams Head On Stage

Sat, 25 Oct Rams Head On Stage

Will Hoge at Rams Head On Stage

Sun, 16 Nov at 08:00 pm Rams Head On Stage

Colin Hay in Annapolis

Tue, 11 Nov at 08:00 pm St. John's College - Francis Scott Key Auditorium

Annapolis Spooky Halloween: A Family Ghost Hunt

Thu, 30 Oct at 05:00 pm 40 Francis St USD 13 to 40

Come & Vibe with the Bay Girlz: Pretty in Pink Brunch

Sun, 19 Oct at 10:00 am The Lodge Annapolis Free

Retirement Master Class & Breakfast at The Lodge

Sat, 15 Nov at 09:30 am The Lodge Annapolis Free

Siren's Call

Fri, 28 Nov at 05:00 pm The Westin Annapolis Free

Thomas Dolby

Thu, 23 Oct at 07:00 pm Rams Head On Stage

Haunted Harbour Day 2025

Sat, 25 Oct at 10:00 am 2512 A Solomons Island Road, Annapolis, MD 21401

Motown and More

Fri, 28 Nov at 07:00 pm Rams Head On Stage

The Prisoner Wine Dinner - Chart House Prime

Thu, 06 Nov at 07:00 pm Chart House USD 159

Crack the Sky

Sat, 01 Nov at 08:00 pm Rams Head On Stage

Pure Prairie League at Rams Head On Stage

Fri, 05 Dec at 08:00 pm Rams Head On Stage

Four80East at Rams Head On Stage

Sat, 25 Oct at 08:00 pm Rams Head On Stage

Jeffrey Gaines & Sawyer Fredericks

Sat, 06 Dec at 07:00 pm Rams Head On Stage

Holistic Business Community November Happy Hour!

Wed, 05 Nov at 05:00 pm Center for Transformative Dentistry Free

Sunday Fun Day & Art Walk in Downtown Annapolis

Sat, 01 Nov at 01:00 pm 172 Green St USD 29 to 50

Richard Thompson at Francis Scott Key Auditorium at St. John's College

Sun, 02 Nov at 07:30 pm Francis Scott Key Auditorium at St. John's College

Siren's Call

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

Full Moon Celebration - December

Fri, 05 Dec at 07:30 pm Unitarian Universalist Church of Annapolis

Jay Hurtt VI of Little Bird at Rams Head On Stage

Wed, 17 Dec at 08:00 pm Rams Head On Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

Sun, 02 Nov at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Shakey Graves

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

The Next Chapter: A Community Book Club

Wed, 19 Nov at 06:00 pm Tatte Bakery & Cafe | Annapolis Free

Natalie Merchant at Maryland Hall for the Creative Arts

Sun, 23 Nov Maryland Hall for the Creative Arts

Halloween Spooktacular! - October 19, 2025

Sun, 19 Oct at 03:00 pm St. John's College USD 0 to 28

Tears for Devere: Autumn in Annapolis!

Sun, 09 Nov at 07:00 pm 49 West Coffeehouse, Winebar & Gallery

Siren's Call

Fri, 12 Dec at 05:00 pm The Westin Annapolis Free

Navy Midshipmen vs. Florida Atlantic Owls

Fri, 24 Oct at 07:00 pm Navy Marine Corps Memorial Stadium

Dan Navarro at Rams Head On Stage

Thu, 06 Nov at 08:00 pm Rams Head On Stage

Fall Festival on Maryland Ave

Sun, 19 Oct at 10:00 am Maryland Avenue, Annapolis