5k Events and Things to do in Leonardtown, MD
A healthy lineup of 5k events and things to do in Leonardtown, MD awaits runners looking to test their pace or enjoy a community jog. Participants typically gather along waterfront trails and neighborhood paths for morning dashes and charitable fun runs. Getting started usually involves checking local running group schedules or registering for seasonal charity trots.
- Scenic waterfront stretches near Breton Bay offer natural backdrops for local running groups and casual morning jogs.
- Community-focused charity runs often start near historic downtown spaces, blending local history with fitness routines.
- Training meetups regularly assemble along paved multi-use paths, giving participants structured environments to build endurance.

Jack-O-Lantern 5K Fun Run
Tomorrow at 7:00 AM
Joint Base Andrews · 1444 Concord Avenue, Joint Base Andrews, MD, USA

Jack-O-Lantern 5K Fun Run
Tomorrow at 7:00 AM
Joint Base Andrews · 1444 Concord Avenue, Joint Base Andrews, MD, USA
JB Andrews 2026 Turkey Trot 5k
Thu, Nov 19, 7:00 AM
Joint Base Andrews · 1444 Concord Avenue, Joint Base Andrews, MD, USA
JB Andrews 2026 Turkey Trot 5k
Thu, Nov 19, 7:00 AM
Joint Base Andrews · 1444 Concord Avenue, Joint Base Andrews, MD, USA
4th Annual Lake Accotink Park Beaver Boogie 5k Run or Walk
Sat, Nov 28, 9:00 AM
Springfield · 7500 Accotink Park Rd
4th Annual Lake Accotink Park Beaver Boogie 5k Run or Walk
Sat, Nov 28, 9:00 AM
Springfield · 7500 Accotink Park Rd
USMSM Doing Business with Government Agencies Speaker Series Session 5
Wed, Jan 20, 5:00 PM
California · 44219 Airport Rd
USMSM Doing Business with Government Agencies Speaker Series Session 5
Wed, Jan 20, 5:00 PM
California · 44219 Airport Rd
2027 5K RUN/WALK OF HOPE | LaMont Dottin Foundation For Missing Persons
Sat, May 22, 8:00 AM
Oxon Hill · 100 MGM National Ave
2027 5K RUN/WALK OF HOPE | LaMont Dottin Foundation For Missing Persons
Sat, May 22, 8:00 AM
Oxon Hill · 100 MGM National Ave
Henderson Hall Ooh Rah Run Series - Haunted Hill 5K
Friday at 7:30 AM
Arlington · Cpl Terry L. Smith Gym
Henderson Hall Ooh Rah Run Series - Haunted Hill 5K
Friday at 7:30 AM
Arlington · Cpl Terry L. Smith Gym
Saturday Night Live Presented by Piano Keys Lounge & WPGC 95.5
Sat, Nov 7, 9:00 PM + 7 more
Brandywine · Piano Keys Restaurant and Lounge
Saturday Night Live Presented by Piano Keys Lounge & WPGC 95.5
Sat, Nov 7, 9:00 PM + 7 more
Brandywine · Piano Keys Restaurant and Lounge
Ooh Rah Run Series - Joint Base Myer- Henderson Hall Turkey Trot 5K
Fri, Nov 20, 7:00 AM
Arlington · Cpl Terry L. Smith Gym
Ooh Rah Run Series - Joint Base Myer- Henderson Hall Turkey Trot 5K
Fri, Nov 20, 7:00 AM
Arlington · Cpl Terry L. Smith Gym
Frequently asked questions about Leonardtown