11 events in Charles County, Maryland

From big races to Saturday morning group runs—find running, cycling, triathlon, and swimming events and connect with the local endurance sports community.

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Indian Head Rail Trail 5k & 10k [bishopsevents.com] [Register at raceroster.com]
Sun, Mar 08, 2026 at 8:30 AM

Description

Come check out one of our flatter courses that traverses along creeks and through woods along the Indian Head Rail Trail.

5k 10k Run Trail
10390 Theodore Green Boulevard, Charles County, Maryland, 20695, United States
OpenStreetMap Google Maps
Shamrock 5K Run/Walk [runsignup.com]
Sun, Mar 15, 2026 at 8:00 AM

Description

*****Race Packets can be picked up on Saturday 1-3 (3/14/26) and Sunday (3/15/26) beginning at 7am at Ape Hangers Bar & Grill. Parking will begin at Ape Hangers and overfill parking will be directed...

*****Race Packets can be picked up on Saturday 1-3 (3/14/26) and Sunday (3/15/26) beginning at 7am at Ape Hangers Bar & Grill. Parking will begin at Ape Hangers and overfill parking will be directed to the Bel Alton Fire Department field (please do not park in the fire departments lot). The race will begin and end at the fire department, which is a short walk from Ape Hangers. After the race, join us at Ape Hangers for food, awards and entertainment.

This year celebrates our 11th Annual Shamrock 5K Run/Walk Fueled by Coal Road Fitness. The race will begin with Lil' Leprechaun 650-meter run at 8:00 am and will be followed by the 5K Run/Walk through the scenic streets of Bel Alton, MD. Awards will be given for top qualifiers in each age group. Participants will receive a t-shirt if registered by 2/28 and all will receive a post-race buffet ticket at Ape Hangers Bar & Grill. An award will be given for the best St. Patricks' Day costume. The early bird race registration fee is $40 and will increase to $45 on 1/1/2025 and to $50 on 3/1/2026.

The beneficiary of this year's race is Clements Cuties. Clements Cuties is dedicated to raising awareness and supporting local families in their fight against childhood cancers in Southern Maryland.

5k Run Walk
9100 Crain Hwy, Charles County, Maryland, 20611, United States
OpenStreetMap Google Maps
3rd Annual Nik-Kicks Kidney Cancer 5k Walk/Run [runsignup.com]
Sat, Mar 21, 2026 at 8:30 AM

Description

March is Kidney Cancer Awareness Month, and this 5k is my way of shining a light, spreading hope and pushing for a cure. Walk, run, cheer -- EVERY STEP MATTERS!!!

Join me March 21. 2026.

Check in and onsite registration open at 8:30 a.m.

THE EVENT KICKS OFF PROMPTLY AT 9:00 AM

Please rock your orange in support of Kidney Cancer!!!

3 Miles 5k Run Walk
10390 Theodore Green Boulevard, Charles County, Maryland, 20695, United States
OpenStreetMap Google Maps
ERWD 3K Fun Run [raceroster.com]
Sat, Apr 04, 2026 at 8:00 AM

Description

Fun run starts at 8 am. Bib pick up 7-8 am, Awards at 9 am

3k Fun Run Run
Deans Place, Charles County, Maryland, 20622, United States
OpenStreetMap Google Maps

STEVE 5K [runsignup.com]
Sat, Apr 25, 2026 at 12:01 AM

Description

SAVE THE DATE! The 6th Annual STEVE 5K will be held on April 25, 2026

The Center for Abused Persons will be holding its 6h Annual event, "Steps To End Violence Everywhere (STEVE) 5K" on Saturday,...

SAVE THE DATE! The 6th Annual STEVE 5K will be held on April 25, 2026

The Center for Abused Persons will be holding its 6h Annual event, "Steps To End Violence Everywhere (STEVE) 5K" on Saturday, April 25 2026. Come on out to White Plains, MD at the Indian Head Rail Trail to run or walk in support of this cause. Our goal is to raise awareness and funds to put an end to domestic and sexual violence in our communities. All proceeds go to victims of abuse and ending violence.

Pre-registered runners will receive an event t-shirt - must be registered by March 29 to be guaranteed a shirt

Race location:

10400 Theodore Green Blvd

White Plains, MD 20695

Race start time: 10:00 am Check in and race day registration begins at 8:00 am

Parking is available at the race site

Course is an out-and-back paved trail

Donations to CAP may be made through this website or on our website: https://www.centerforabusedpersonscharlescounty.org/, by mailing a check or through payroll deduction via the United Way of Charles County, the Maryland Charity Campaign (agency # 52-1280683) or the Combined Federal Campaign (agency # 55562)

This race is being professionally timed and managed by Blue Cheetah Sports Timing

5k 3.11 Miles Run Trail Walk
10390 Theodore Green Boulevard, Charles County, Maryland, 20695, United States
OpenStreetMap Google Maps
General Smallwood Triathlon [kineticmultisports.com] [Register at runsignup.com]
Sat, Apr 25, 2026 at 8:00 AM

Description

Staged out of beautiful General Smallwood State Park, this triathlon has beautiful, rolling courses and low traffic roads. The swim takes place in the Mattawoman Bay, known across the Nation as a...

Staged out of beautiful General Smallwood State Park, this triathlon has beautiful, rolling courses and low traffic roads. The swim takes place in the Mattawoman Bay, known across the Nation as a prime example of what a fully restored Chesapeake Bay tributary looks like! After a quick run to the transition area, athletes will race along the rolling, freshly paved, low traffic roads of Charles County. Once you’ve laced up your running shoes, you’ll head back to the road for another scenic, rolling course with aid stations every mile. The last mile of the course is amazing as you re-enter the park and cross over Mattowoman Bay just prior to the finish line and your fantastic post race BBQ. Don’t miss out on this early season classic just a short drive from NOVA!

On the fence about registering? Check out our General Smallwood Triathlon Video and sign up today!

For more details please go to: https://kineticmultisports.com/races/smallwood/

Run Swim Triathlon
2750 Sweden Point Rd, Charles County, Maryland, 20658, United States
OpenStreetMap Google Maps
2026 Cal Tri DC - 6.14.26 [runsignup.com]
Sun, Jun 14, 2026 at 8:00 AM

Description

2026 Cal Tri DC - 6.14.26. Combine a trip to the nation's capitol with a race venue just 30 miles south of Washington DC in Maryland's General Smallwood State Park.

18 EVENT OPTIONS. 6 Olympic...

2026 Cal Tri DC - 6.14.26. Combine a trip to the nation's capitol with a race venue just 30 miles south of Washington DC in Maryland's General Smallwood State Park.

18 EVENT OPTIONS. 6 Olympic distance events (Triathlon, RunBikeRun, SwimBike, SwimRun, 1640 Yard Swim & 10K Run), 6 Sprint distance events (Triathlon, RunBikeRun, SwimBike, SwimRun, 400 yard Swim & 5K Run) and 6 Youth Sprint distance events (Triathlon, RunBikeRun, SwimBike, SwimRun, 400 yard Swim & 5K Run). Triathlon = swim + bike + run. Typically, the swim and run distances are standard but the bike distance varies from race to race. Check out the course maps for more detailed information.

TO DO. Smithsonian National Museum of Natural History. National Museum of African American History and Culture. US Capitol.

AIRPORT. Ronald Reagan Washington National (DCA)

AIR TEMPERATURE (AVG). 64 F / 86 F

WATER TEMPERATURE (AVG). 82 F. Wetsuit allowed with no results. Use the 20% CALTRI2025 discount code at blueseventy. Note: Fusion wetsuits not eligible for discount.

Aquabike Cycling Duathlon Run Swim SwimRun Triathlon
Charles County, Maryland, 20658, United States
OpenStreetMap Google Maps
Trick Or Trot Crab Trot 5K [runsignup.com]
Sat, Oct 24, 2026 at 9:00 AM
Description
Invitation

Lace up your sneakers and join us on Saturday, October 25, 2025, for the 3rd Annual Cobb Island Crab Trot 5K Run/Walk!

Bring your family, your friends, your neighbors—and even your...
Invitation

Lace up your sneakers and join us on Saturday, October 25, 2025, for the 3rd Annual Cobb Island Crab Trot 5K Run/Walk!

Bring your family, your friends, your neighbors—and even your neighbors' friends! Everyone is welcome to participate in this fun-filled community event.

The 5K course circles the perimeter of Cobb Island, offering beautiful scenic views of Neale Sound, the Potomac River, and the Wicomico River.

Come dressed in your favorite crab-themed costume or attire—there will be a prize for the best look!

This family-friendly event is open to all ages and fitness levels, whether you're a seasoned runner, a weekend jogger, or just out for a walk.

Rain or shine, the race goes on. Please note: no refunds or deferrals.

Timing

Chip timing is provided by Overland Timing.

Registration

Standard Registration- $40, Register by October 4, 2025, to guarantee your commemorative finisher medal and race day T-shirt! Fee changes to $50 after October 4, 2025.

REGISTRATION INCLUDES, if registered by October 4, 2025:
- Race Bib
- Finisher Medal
- Trick or Trot Crab Trot T-Shirt
- Pre and Post Snacks
Race Packet Pick-up

Friday, October 24, 2025. Cobb Island Citizens Association Hall, 13201 Main Avenue, Cobb Island, MD.

6:00 pm -8:00 pm

Race Day Timeline

Saturday, October 25, 2025, Fisherman’s Field, Cobb Island

7:30am-8:45am: Race Day packet pickup, there is still time to register

8:45am-8:55am: Opening Ceremony

8:55am-9:00am: Group Photo and Prize awarded for Best Crab themed attire or costume

9:00am-10:30am: Trick or Trot Crab Trot 5K Run/Walk

10:00am-10:30am: Winners medals awarded

Recognition

Prize awarded for best crab attire/costume.

Medals awarded to the top male and female finishers in each age category.

Age Categories-
- 11 and under
- 12-19
- 20-29
- 30-39
- 40-49
- 50-59
- 60-69
- 70-79
- 80 and up
Non-Profit

This event is hosted by Cobb Island Citizens Association, a non-profit organization and sponsored by businesses right here in your County. All proceeds go back to the Community of Cobb Island through various opportunities and events. Visit www.mycobbisland.org

Facebook

Like and share our Facebook page: Cobb Island Crab Trot 5K Run/Walk
5k Run Walk
Charles County, Maryland, 20625, United States
OpenStreetMap Google Maps
We Got Your Six Running Festival [runsignup.com]
Sun, Nov 01, 2026 at 9:00 AM

Description

The Grainger Group invites you to join their 4th Annual We Got Your Six Running Festival on the Indian Head Rail Trail in Charles County, MD, benefiting the Tunnel to Towers Foundation.

*This race is capped at 200 participants so register today to claim your spot!

*NEW START TIME OF 8AM FOR 2026

10k 13.1 Miles 26.2 Miles Run Trail
10390 Theodore Green Boulevard, Charles County, Maryland, 20695, United States
OpenStreetMap Google Maps
Indian Head Turkey Trot 5k & 10k [bishopsevents.com] [Register at raceroster.com]
Sat, Nov 14, 2026 at 7:45 AM

Description

Come run one of our flat, scenic courses that traverses along creeks and through woods along the Indian Head Rail Trail.

5k 10k Run Trail
Indian Head Rail Trail, Charles County, Maryland, 20695, United States
OpenStreetMap Google Maps
Y Turkey Trot Charity 5K [runsignup.com]
Thu, Nov 26, 2026 at 8:30 AM

Description

You’re invited to continue your Thanksgiving tradition (or start a new one!) with the Y!

The Trot is a guaranteed way to get a healthy start to your day and do something good for your community. It...

You’re invited to continue your Thanksgiving tradition (or start a new one!) with the Y!

The Trot is a guaranteed way to get a healthy start to your day and do something good for your community. It also makes you feel better about the pie. Trust us.

With six race locations across central Maryland, the Y Turkey Trot Charity 5K is for people of all ages and abilities. Everyone is welcome (including your pup!)

5k Run
State Hwy 6, Charles County, Maryland, 20640, United States
OpenStreetMap Google Maps

Local Clubs & Organizations

Southern Maryland Aquatics Club

[southernmarylandaquatics.com] [usaswimming.org]
USA Swimming Club. 116 members.

Swim

Contact: CoachKyle@southernmarylandaquatics.com
3000 Chicamuxen Rd, Charles County, Maryland, 20640-3404, United States
OpenStreetMap Google Maps
Phone: +1 541-217-1277

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