Trips & Adventurous Activities in Annapolis

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

Spyro Gyra

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

Undead Mile Run – Annapolis, MD

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

Tall Tall Trees & Christopher Paul Stelling

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

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

 Fri, 24 Oct 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

Crack the Sky at Rams Head On Stage

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

Macy Gray at Rams Head On Stage

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

Will Hoge

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

Keb Mo at Maryland Hall for the Creative Arts

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

GA20 at Rams Head On Stage

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

Ketch Secor

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

Tall Tall Trees at Rams Head On Stage

 Sat, 25 Oct Rams Head On Stage

Thomas Dolby

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

Motown and More

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

Pure Prairie League at Rams Head On Stage

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

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

Shakey Graves

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

Dan Navarro at Rams Head On Stage

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

Thomas Dolby

 Sat, 25 Oct Rams Head On Stage - Annapolis

Chris Isaak at Maryland Hall for the Creative Arts

 Sun, 07 Dec at 08:00 pm Maryland Hall for the Creative Arts

Richard Thompson

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

Marshall Crenshaw

 Thu, 13 Nov at 07:00 pm Rams Head On Stage

Funny How Marriage Works Date Night Experience

 Sat, 25 Oct at 07:30 pm Church of Severn

The Jerry Douglas Band at Rams Head On Stage

 Wed, 05 Nov at 08:00 pm Rams Head On Stage

Carbon Leaf

 Fri, 12 Dec at 07:00 pm Rams Head On Stage

Pete Correale

 Thu, 06 Nov at 07:00 pm Rams Head On Stage

PARKING: Military Bowl

 Fri, 26 Dec at 07:00 pm Navy Marine Corps Memorial Stadium Parking Lots

Four80East

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

Family Art Nights at ArtFarm

 Fri, 24 Oct at 05:00 pm 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401

Jon McLaughlin at Rams Head On Stage

 Sun, 21 Dec at 07:30 pm Rams Head On Stage

Military Bowl

 Fri, 26 Dec Navy Marine Corps Memorial Stadium

Tab Benoit at Rams Head On Stage

 Sun, 07 Dec Rams Head On Stage

Jarrod Lawson concert at Rams Head On Stage

 Sat, 17 Jan at 08:00 pm Rams Head On Stage

Uli Jon Roth

 Wed, 12 Nov at 07:00 pm Rams Head On Stage

Danny Burns Band

 Sun, 21 Dec at 07:00 pm Rams Head On Stage

The Secret Sisters

 Sun, 26 Oct at 07:00 pm Rams Head On Stage

The Brit Pack at Rams Head On Stage

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

Wishbone Ash

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

Ana Popovic

 Sat, 10 Jan at 07:00 pm Rams Head On Stage

Kashmir - The Led Zeppelin Experience

 Fri, 09 Jan at 07:00 pm Rams Head On Stage

SOFO Summer Drive-In Movies Under the Stars - October 2025

 Fri, 24 Oct at 06:30 pm Bay Ridge Plaza 123 Hillsmere Dr, Annapolis MD 21403

The Carole King & James Taylor Story - Tribute Show

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

Parking - Florida Atlantic Owls at Navy Midshipmen Football

 Sat, 25 Oct Navy-Marine Corps Memorial Stadium

SOD-O Holiday Party

 Sat, 06 Dec at 06:00 pm Acqua al 2 - Annapolis USD 0 to 100

Halloween Ghost Hunt in Annapolis

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

Scenic Rivers Land Trust's Conservation Celebration 2025

 Thu, 23 Oct at 06:00 pm Philip Merrill Environmental Center USD 121 to 135

Atlanta Rhythm Section at Rams Head On Stage

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

A Peter White Christmas at Rams Head On Stage

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

The Martin Sexton Abbey Road Show at Rams Head On Stage

 Fri, 21 Nov at 08:00 pm Rams Head On Stage

Mindi Abair & Vincent Ingala

 Wed, 03 Dec at 07:00 pm Rams Head On Stage

Colin Hay

 Mon, 10 Nov at 07:00 pm Francis Scott Key Auditorium

Paula Poundstone

 Thu, 18 Dec at 07:00 pm Rams Head On Stage

First Sunday Arts Festival

Sun, 02 Nov at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Pure Prairie League

 Thu, 04 Dec at 07:00 pm Rams Head On Stage

Tab Benoit

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

Atlanta Rhythm Section

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

Military Bowl at Navy Marine Corps Memorial Stadium

 Sat, 27 Dec at 11:00 am Navy Marine Corps Memorial Stadium

Emma Nissen

 Sun, 16 Nov Rams Head On Stage

Happy Holidays Drag Brunch

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Carbon Leaf at Rams Head On Stage

 Fri, 12 Dec at 08:30 pm Rams Head On Stage

Walktober!

 Wed, 22 Oct at 05:15 pm Graduate Annapolis

The Art Bar

 Thu, 20 Nov at 06:00 pm 1851 McGuckian Street, Annapolis, MD, United States, Maryland 21401

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

 Thu, 22 Jan at 07:00 pm Rams Head On Stage

The Seldom Scene

 Mon, 29 Dec at 07:00 pm Rams Head On Stage

Satisfaction - The International Rolling Stones Tribute Show

 Sat, 31 Jan at 07:00 pm Rams Head On Stage

Jarrod Lawson

 Fri, 16 Jan at 07:00 pm Rams Head On Stage

Annapolis M**der Mystery: Solve the case!

 Sat, 31 May at 04:00 pm 101 State Cir USD 10 to 30

Danah Denice Band

 Thu, 15 Jan at 07:00 pm Rams Head On Stage

The High Kings at Rams Head On Stage

 Sun, 08 Mar Rams Head On Stage

Annapolis Conspiracy Game: The Outdoor Escape

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

Dar Williams & Seth Glier

 Thu, 05 Feb Rams Head On Stage

Annapolis' Secret Society: Mystery Hunt

 Sat, 26 Jul at 05:00 pm 43 Calvert St USD 10 to 20

PARKING: Navy Midshipmen vs. Florida Atlantic Owls

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

PARKING: Navy Midshipmen vs. South Florida Bulls

 Fri, 14 Nov at 07:00 pm Navy Marine Corps Memorial Stadium Parking Lots

South Florida Bulls at Navy Midshipmen Football

 Sat, 15 Nov at 08:30 am Navy-Marine Corps Memorial Stadium

Speaker: The How of WOW!!! by Karl Gercens, Longwood Gardens Conservatory Manager

 Tue, 04 Nov at 07:00 pm 1223 River Bay Road, Annapolis, MD, United States, Maryland 21409

The Bacon Brothers

 Wed, 21 Jan at 07:00 pm Maryland Hall For The Creative Arts

The Secret Sisters

 Tue, 28 Oct at 12:00 am Rams Head On Stage - Annapolis

AJ Croce - Croce Plays Croce at Rams Head On Stage

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

Philadelphia’s Fairmount Park Historic Homes – Bus Tour with Historic Annapolis

 Thu, 06 Nov at 08:00 am Maryland Hall

Marshall Crenshaw

 Sat, 15 Nov at 01:00 am Rams Head On Stage - Annapolis

Son Little at Rams Head On Stage

 Tue, 02 Dec at 08:00 pm Rams Head On Stage

After Dark Ghost Hunt in Annapolis: Face the Fright!

 Wed, 10 Sep at 06:00 pm 40 Francis St USD 10 to 20

Ghosts of Annapolis: Join the Hunt!

 Fri, 05 Sep at 05:00 pm 40 Francis St USD 10 to 20

Motown and More

 Sun, 30 Nov at 02:30 am Rams Head On Stage - Annapolis

Florida Atlantic Owls at Navy Midshipmen Football

 Sat, 25 Oct at 07:30 am Navy-Marine Corps Memorial Stadium

Candlelight: Coldplay & Imagine Dragons | Annapolis

 Sun, 14 Dec at 06:30 pm Annapolis Waterfront Hotel

Richard Thompson

 Mon, 03 Nov at 12:30 am Frances Scott Key Auditorium

Vienna Teng

 Wed, 19 Nov at 07:00 pm Rams Head On Stage

The Empty Pockets

 Tue, 02 Dec at 07:00 pm Rams Head On Stage

Burning Witches

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

Micky Dolenz at Rams Head On Stage

 Tue, 04 Nov at 08:00 pm Rams Head On Stage

The Secret Sisters at Rams Head On Stage

 Mon, 27 Oct at 08:00 pm Rams Head On Stage

Jim Messina at Rams Head On Stage

 Tue, 25 Nov at 08:00 pm Rams Head On Stage

Bruce in the USA - Bruce Springsteen Tribute

 Sat, 24 Jan at 01:00 am Rams Head On Stage

Keb Mo

 Thu, 20 Nov at 07:00 pm Maryland Hall For The Creative Arts

Colin Hay at Francis Scott Key Auditorium at St. John's College

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

Conspiracy Scavenger Hunt in Annapolis

 Sat, 26 Jul at 10:00 am 43 Calvert St USD 10 to 20

Crack The Sky

 Thu, 30 Oct at 07:00 pm Rams Head On Stage

Acoustic Alchemy

 Tue, 11 Nov at 07:00 pm Rams Head On Stage