Trips & Adventurous Activities in Annapolis

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

Carpool - Tribute to The Cars

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

The Bacon Brothers

 Sat, 30 Aug at 07:00 pm Maryland Hall For The Creative Arts

The Blue Genies - Celebrating The Music of David Bowie

 Fri, 29 Aug at 07:00 pm Rams Head On Stage

Navy Midshipmen vs. UAB Blazers

 Fri, 05 Sep at 07:00 pm Navy Marine Corps Memorial Stadium

10000 Maniacs at Rams Head On Stage

 Sat, 13 Sep at 08:30 pm Rams Head On Stage

Mindi Abair at Rams Head On Stage

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

Joe Pug at Rams Head On Stage

 Sat, 27 Sep at 08:00 pm Rams Head On Stage

Technicolor Motor Home - A Steely Dan Tribute

 Sat, 11 Oct at 07:00 pm Rams Head On Stage

Pets & Pet Inventions with Girl Scouts!!!

 Sun, 17 Aug at 03:30 pm Michael E. Busch Annapolis Library Free

Mike Phillips at Rams Head On Stage

 Thu, 21 Aug at 08:00 pm Rams Head On Stage

Skerryvore

 Sun, 07 Sep at 07:00 pm Rams Head On Stage

Jimmie Vaughan at Rams Head On Stage

 Sat, 16 Aug at 08:00 pm Rams Head On Stage

Adam Ezra Group

 Sat, 16 Aug at 07:00 pm Rams Head On Stage

Shaun Cassidy at Rams Head On Stage

 Sat, 18 Oct at 08:00 pm Rams Head On Stage

Casey Abrams

 Sun, 14 Sep at 07:00 pm Rams Head On Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 31 Aug at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Jonathan Coulton at Rams Head On Stage

 Thu, 04 Sep 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

Tim O Brien at Rams Head On Stage

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

The Weight Band

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

The Australian Bee Gees

 Sat, 04 Oct at 07:00 pm Rams Head On Stage

Winterthur Bus Trip

 Sat, 27 Sep at 10:00 am 1223 River Bay Road, Annapolis, MD, United States, Maryland 21409

The Hot Sardines at Rams Head On Stage

 Thu, 18 Sep Rams Head On Stage

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

 Fri, 22 Aug at 06:00 pm Bay Ridge Plaza 123 Hillsmere Dr, Annapolis MD 21403

Navy Midshipmen vs. Florida Atlantic Owls

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

Steep Canyon Rangers at Maryland Hall for the Creative Arts

 Thu, 11 Sep at 08:00 pm Maryland Hall for the Creative Arts

Dirty Heads

 Thu, 11 Sep at 07:00 pm Calvert Street Stage

Chris Standring at Rams Head On Stage

 Wed, 10 Sep at 08:00 pm Rams Head On Stage

Tuba Skinny at Rams Head On Stage

 Fri, 29 Aug at 08:00 pm Rams Head On Stage

Maysa

 Fri, 19 Sep Rams Head On Stage

The Next Chapter: A Community Book Club

 Wed, 20 Aug at 06:00 pm Tatte Bakery & Cafe | Annapolis Free

Pops in the Park - Quiet Waters Park

 Sun, 31 Aug at 05:30 pm Quiet Waters Park Rd, Annapolis, MD 21403, United States

Four80East

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

Nils at Rams Head On Stage

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

Nils & Jeff Kashiwa

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

Undead Mile Run – Annapolis, MD

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

Navy Midshipmen vs. Virginia Military Keydets

 Fri, 29 Aug at 07:00 pm Navy Marine Corps Memorial Stadium

Annapolis Midnight Mile Vampire Run

 Sat, 11 Oct at 06:00 pm Annapolis, Annapolis, Maryland

Rams Head Presents Al Jardine and The Pet Sounds Band - Annapolis, MD

 Sat, 13 Sep at 08:00 pm Maryland Hall

Danny Burns

 Fri, 29 Aug at 07:00 pm Rams Head On Stage

Scandalous Annapolis

 Sat, 06 Sep at 07:30 pm 188 Main St, Annapolis, MD 21401-2008, United States

10 000 Maniacs

 Fri, 12 Sep Rams Head On Stage

Full Moon Paddle-Back Creek Annapolis

 Sun, 07 Sep at 06:30 pm Ellen O. Moyer Nature Park at Back Creek

Hermans Hermits

 Sat, 27 Sep 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

Michael Yo

 Sat, 20 Sep Rams Head On Stage

Summer Neurodivergent Teen Social Club

 Sun, 17 Aug at 04:45 pm 205 Ridgely Ave, Annapolis, MD, United States, Maryland 21401

Anchors & Artisans @ Annapolis Town Center

 Sun, 24 Aug at 11:00 am Annapolis Town Center

First Sunday Arts Festival

Sun, 07 Sep at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Family Art Nights at ArtFarm

 Fri, 19 Sep at 05:00 pm 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401

PARKING: Navy Midshipmen vs. Rice Owls

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

Michael Yo at Rams Head On Stage

 Sun, 21 Sep Rams Head On Stage

Maysa at Rams Head On Stage

 Sat, 20 Sep Rams Head On Stage

Navy Midshipmen vs. Rice Owls

 Fri, 26 Sep at 07:00 pm Navy Marine Corps Memorial Stadium

Timmie Metz Band

 Thu, 21 Aug at 07:00 pm Rams Head On Stage

The Doo Wop Project (21+)

 Sat, 16 Aug at 12:00 am Rams Head On Stage - Annapolis

Navy Midshipmen vs. Air Force Falcons

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

Greg Hawkes at Rams Head On Stage

 Fri, 03 Oct at 08:00 pm Rams Head On Stage

Dan Navarro at Rams Head On Stage

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

Skipjack Race Watch Party on MILDRED BELLE

 Sun, 14 Sep at 11:00 am Sandy Point State Park USD 13 to 45

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

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

Crack the Sky at Rams Head On Stage

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

Shaun Cassidy

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

The Imaginary Invalid

 Mon, 11 Aug at 07:00 pm Reynolds Tavern

Kids on the Creek

 Sun, 24 Aug at 11:00 am Truxton Park Boat Ramp

The Brit Pack at Rams Head On Stage

 Sat, 22 Nov Rams Head On Stage

Ocean City Rock & Ride

Fri, 12 Sep at 08:00 am Annapolis Mall

Atlanta Rhythm Section at Rams Head On Stage

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

Yasmin Williams at Rams Head On Stage

 Thu, 02 Oct at 08:00 pm Rams Head On Stage

Sunrise Paddle

 Sat, 16 Aug at 06:00 am 655 Americana Dr, Annapolis, MD 21403, United States

Chesapeake Region Accessible Boating (CRAB) Group Sail

 Tue, 19 Aug at 01:30 pm 7040 Bembe Beach Rd, Annapolis, MD 21403-3107, United States

PARKING: Military Bowl

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

Chris Isaak

 Sat, 06 Dec at 07:00 pm Maryland Hall For The Creative Arts

Carbon Leaf at Rams Head On Stage

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

Kashmir - The Led Zeppelin Experience

 Fri, 09 Jan 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

The Martin Sexton Abbey Road Show at Rams Head On Stage

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

The Amish Outlaws

 Thu, 16 Oct at 07:00 pm Rams Head On Stage

The Ocean Blue & Brian Tighe of The Hang Ups

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

2025 Bay Bridge Run 10K

 Sun, 09 Nov at 05:30 am Annapolis, MD

Military Bowl

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

American Aquarium at Rams Head On Stage

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

Chris Isaak at Maryland Hall for the Creative Arts

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

Tab Benoit at Rams Head On Stage

 Sun, 07 Dec Rams Head On Stage

Thomas Dolby

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

Sierra Hull with John Craigie

 Wed, 08 Oct at 12:00 am Rams Head On Stage - Annapolis

Pete Correale

 Thu, 06 Nov Rams Head On Stage

Pure Prairie League

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

Paula Poundstone

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

Tom Sandoval at Rams Head On Stage

 Tue, 30 Sep at 08:00 pm Rams Head On Stage

In the Vane of 80s Ladies at Rams Head On Stage

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

PARKING: Navy Midshipmen vs. South Florida Bulls

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

Sheena Easton at Rams Head On Stage

 Tue, 09 Sep at 08:00 pm Rams Head On Stage

Skerryvore at Rams Head On Stage

 Mon, 08 Sep at 08:00 pm Rams Head On Stage

Ari Hest at Rams Head On Stage

 Wed, 24 Sep at 08:00 pm Rams Head On Stage

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 Ocean Blue at Rams Head On Stage

 Thu, 09 Oct at 08:00 pm Rams Head On Stage

The Hot Sardines

 Wed, 17 Sep at 07:00 pm Rams Head On Stage

Nils

 Sun, 07 Sep at 12:00 am Rams Head On Stage - Annapolis