Trips & Adventurous Activities in Annapolis

Check out happening trips & adventurous activities events all around Annapolis, MD

Maryland Day Celebration 2026 - filled with fun events!

 Thu, 19 Mar at 10:00 am Across Annapolis & Anne Arundel County, MD, United States, Maryland

Matisyahu

 Tue, 03 Mar at 07:00 pm Rams Head On Stage

John Moreland & Patterson Hood

 Sat, 14 Mar Rams Head On Stage

Graham Nash at Maryland Hall for the Creative Arts

 Tue, 14 Apr at 07:30 pm Maryland Hall for the Creative Arts

Spyro Gyra

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

The High Kings at Rams Head On Stage

 Sun, 08 Mar at 05:00 pm Rams Head On Stage

Graham Parker at Rams Head On Stage

 Sat, 02 May at 08:00 pm Rams Head On Stage

Madeleine Peyroux at Rams Head On Stage

 Mon, 11 May at 08:00 pm Rams Head On Stage

Marcus Miller at Rams Head On Stage

 Sun, 24 May at 05:00 pm Rams Head On Stage

John Moreland and Patterson Hood

 Sun, 15 Mar at 11:00 pm Rams Head On Stage - Annapolis

Joanne Shaw Taylor at Rams Head On Stage

 Sat, 28 Mar at 08:00 pm Rams Head On Stage

Al Di Meola Electric Band

 Fri, 08 May Rams Head On Stage

Premier Lacrosse League - All Star at Navy Marine Corps Memorial Stadium

 Sun, 05 Jul at 02:00 pm Navy Marine Corps Memorial Stadium

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

 Mon, 09 Mar at 08:00 pm Rams Head On Stage

Premier Lacrosse League - All-Star Games

 Sun, 05 Jul at 06:00 pm Navy-Marine Corps Memorial Stadium

Marcus Miller

 Sat, 23 May at 07:00 pm Rams Head On Stage

Uli Jon Roth

 Mon, 27 Apr at 07:00 pm Rams Head On Stage

Colgate Raiders at Navy Midshipmen Mens Lacrosse

 Sat, 28 Mar at 04:00 pm Navy-Marine Corps Memorial Stadium

Madeleine Peyroux

 Sun, 10 May at 07:00 pm Rams Head On Stage

Pablo Cruise at Rams Head On Stage

 Sun, 31 May at 08:00 pm Rams Head On Stage

Tommy Castro & The Painkillers

 Mon, 20 Apr at 12:00 am Rams Head On Stage - Annapolis

Jonathan Butler

 Fri, 17 Apr at 07:00 pm Rams Head On Stage

Annapolis First Sunday Arts Festival

Sun, 03 May at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Karla Bonoff

 Wed, 18 Mar at 07:00 pm Rams Head On Stage

Eddie Money Legacy Band at Rams Head On Stage

 Fri, 17 Apr at 08:00 pm Rams Head On Stage

Sue Foley

 Thu, 12 Mar at 07:00 pm Rams Head On Stage

The High Kings

 Sun, 08 Mar at 09:00 pm Rams Head On Stage - Annapolis

Albert Castiglia

 Sat, 07 Mar at 06:00 pm Rams Head On Stage - Annapolis

Annapolis Restaurant Week

 Sat, 21 Feb at 08:00 am Downtown Annapolis Partnership Free

Reverend Horton Heat at Rams Head On Stage

 Wed, 08 Apr at 08:00 pm Rams Head On Stage

Mike Doughty

 Fri, 10 Apr at 07:00 pm Rams Head On Stage

Navy Midshipmen Lacrosse vs. Bucknell Bison

 Fri, 06 Mar at 07:00 pm Navy Marine Corps Memorial Stadium

Albert Castiglia at Rams Head On Stage

 Sat, 07 Mar at 01:00 pm Rams Head On Stage

Aaron Gillespie at Rams Head On Stage

 Tue, 10 Mar at 08:00 pm Rams Head On Stage

Albert Lee

 Sun, 15 Mar at 07:00 pm Rams Head On Stage

Taj Farrant at Rams Head On Stage

 Wed, 18 Mar at 08:00 pm Rams Head On Stage

Penny and Sparrow

 Wed, 08 Apr at 07:00 pm Rams Head On Stage

Navy Midshipmen Lacrosse vs. Holy Cross Crusaders

 Fri, 03 Apr at 07:00 pm Navy Marine Corps Memorial Stadium

The David Wax Museum at Rams Head On Stage

 Fri, 10 Apr at 08:00 pm Rams Head On Stage

Toast - The Best of Bread at Rams Head On Stage

 Mon, 13 Apr at 08:00 pm Rams Head On Stage

Bucknell Bisons at Navy Midshipmen Mens Lacrosse

 Sat, 07 Mar at 05:00 pm Navy-Marine Corps Memorial Stadium

David Wax Museum & Elizabeth and the Catapult

 Thu, 09 Apr at 07:00 pm Rams Head On Stage

Quinn Sullivan at Rams Head On Stage

 Sat, 21 Mar at 01:00 pm Rams Head On Stage

Duane Betts & Palmetto Motel

 Mon, 20 Apr at 07:00 pm Rams Head On Stage

Femmes of Rock

 Sat, 25 Apr at 12:00 am Rams Head On Stage - Annapolis

Duane Betts at Rams Head On Stage

 Tue, 21 Apr at 08:00 pm Rams Head On Stage

End of the Line - Allman Brothers Tribute

 Sat, 21 Mar at 12:00 am Rams Head On Stage - Annapolis

Joanne Shaw Taylor

 Sun, 29 Mar at 12:00 am Rams Head On Stage - Annapolis

Bill Kirchen at Rams Head On Stage

 Sun, 17 May at 01:00 pm Rams Head On Stage

Burning Witches

 Tue, 31 Mar at 07:00 pm Rams Head On Stage

Pablo Cruise

 Sat, 30 May at 07:00 pm Rams Head On Stage

Stephen Lynch

 Fri, 05 Jun at 07:00 pm Rams Head On Stage

The Psychology of Serial Killers - Annapolis

 Mon, 04 May at 12:00 am Rams Head On Stage - Annapolis

Back To The Garden 1969 at Rams Head On Stage

 Thu, 12 Mar at 08:00 pm Rams Head On Stage

Celtic Cinco de Mayo with La Unica at Rams Head On Stage

 Tue, 05 May at 08:00 pm Rams Head On Stage

Taj Farrant

 Tue, 17 Mar at 07:00 pm Rams Head On Stage

Green River - Tribute to CCR and John Fogerty

 Fri, 06 Mar at 07:00 pm Rams Head On Stage

Parking Quinn Sullivan

 Sat, 21 Mar at 05:00 pm Rams Head On Stage - Annapolis

Parking Jonathan Butler

 Sat, 18 Apr at 10:30 pm Rams Head On Stage - Annapolis

Nao Yoshioka at Rams Head On Stage

 Thu, 28 May at 08:00 pm Rams Head On Stage

Parking Sons of Cream

 Sat, 28 Feb at 01:00 am Rams Head On Stage - Annapolis

Parking The Phil Collins Experience

 Wed, 18 Mar at 12:00 am Rams Head On Stage - Annapolis

Cole Chaney & The Local Honeys

 Mon, 06 Apr at 07:00 pm Rams Head On Stage

A Tale of Two Cities

 Wed, 25 Feb at 07:00 pm Main Stage At Classic Theatre of Maryland

Thunder from Down Under

 Thu, 26 Mar at 07:00 pm Rams Head On Stage

Burning Witches

 Thu, 02 Apr at 12:00 am Rams Head On Stage - Annapolis

Parking Spyro Gyra

 Fri, 06 Mar at 01:00 am Rams Head On Stage - Annapolis

The Good Deale Bluegrass & Eastman String Band

 Sun, 22 Mar at 12:00 am Rams Head On Stage - Annapolis

Sirens of Spring at Rams Head On Stage

 Thu, 07 May at 08:00 pm Rams Head On Stage

Shelby Morgan at Rams Head On Stage

 Thu, 02 Apr Rams Head On Stage

Parking Loyola Maryland Greyhounds at Navy Midshipmen Womens Basketball

 Thu, 05 Mar at 12:00 am Alumni Hall - Navy

Parking Duane Betts & Palmetto Motel

 Wed, 22 Apr at 12:00 am Rams Head On Stage - Annapolis

John Moreland at Rams Head On Stage

 Sun, 15 Mar at 07:00 pm Rams Head On Stage

USNA Alumni Travel showcase

 Fri, 13 Mar at 03:00 pm 301 King George Street, Annapolis, MD, United States, Maryland 21402

Candlelight: Tribute to Taylor Swift

 Fri, 03 Apr at 07:00 pm Maryland Hall For The Creative Arts

Toast - The Ultimate Bread Experience

 Sun, 12 Apr Rams Head On Stage

Wellness With a Little Drama

 Thu, 04 Jun at 06:30 pm 2158 Renard Ct Free

Matisyahu at Rams Head On Stage

 Wed, 04 Mar at 08:00 pm Rams Head On Stage

Know Return at Rams Head On Stage

 Sun, 29 Mar at 08:00 pm Rams Head On Stage

Become a GRIT Architect: Design a Life That Withstands Hard Moments

 Mon, 13 Apr at 06:30 pm 2158 Renard Ct Free

Cherish the Ladies

 Mon, 02 Mar at 07:00 pm Rams Head On Stage

Parking Hollywood Nights

 Fri, 27 Mar at 12:00 am Rams Head On Stage - Annapolis

Quinn Sullivan

 Sat, 21 Mar at 05:00 pm Rams Head On Stage - Annapolis

Parking Albert Lee

 Tue, 17 Mar at 12:00 am Rams Head On Stage - Annapolis

Women, Wine, & Wisdom™ Annapolis -Field Trip to K&B Ace Hardware

 Tue, 18 Aug at 06:00 pm K&B Ace Hardware

USNA Central PA Parents' Club Bus Trip & Campus Tour 2026

 Sat, 21 Mar at 07:00 am United States Naval Academy, Blake Road, Annapolis, MD, USA Free

Annapolis Conspiracy Game: The Outdoor Escape

 Sat, 26 Jul at 03:00 pm 43 Calvert St USD 10 to 30

Annapolis Spring Sailboat Show

 Thu, 23 Apr at 07:00 pm Annapolis City Dock

Colin James at Rams Head On Stage

 Wed, 06 May at 08:00 pm Rams Head On Stage

BBMak at Rams Head On Stage

 Wed, 22 Apr at 08:00 pm Rams Head On Stage

Parking End of the Line - Allman Brothers Tribute

 Sat, 21 Mar at 12:00 am Rams Head On Stage - Annapolis

Puzzling Adventures Scavenger Hunt - Annapolis

 Sat, 22 Feb at 11:00 am Recommended Parking to Begin Adventure USD 38

Colin James Matt Anderson & Terra Lightfoot

 Tue, 05 May at 07:00 pm Rams Head On Stage

Absolute Adele - Tribute to Adele

 Sun, 19 Apr at 05:00 pm Rams Head On Stage - Annapolis

Sons of Cream

 Sat, 28 Feb at 01:00 am Rams Head On Stage - Annapolis

Parking The Good Deale Bluegrass & Eastman String Band

 Sun, 22 Mar at 12:00 am Rams Head On Stage - Annapolis

Amazing Annapolis Scavenger Hunt

 Wed, 14 Jun at 11:00 am Brown Mustache Coffee, LLC USD 25

Join Us for a Homeschool Meet-Up at Quiet Waters Park - Pirate’s Cove

 Fri, 24 Apr at 11:00 am Quiet Waters Park Annapolis, Md

Loyola Maryland Greyhounds at Navy Midshipmen Mens Lacrosse

 Fri, 24 Apr at 11:00 pm Navy-Marine Corps Memorial Stadium

Walking Tour: Lost History of Frederick (Bailey) Douglass in Old Annapolis

 Sat, 15 Feb at 08:15 am Kunta Kinte-Alex Haley Memorial USD 16 to 23