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9 walking events in Chesapeake, Virginia

From big races to Saturday morning group runs—find walking events and connect with the local endurance sports community.

  • Responders Ruck [runsignup.com]

    Sat, Jan 17, 2026 at 6:30 AM

    Description

    FREE event at Bells Mill Park in Chesapeake, VA! Come on out and enjoy the morning with fellow first responders on the same mission to be the best version of themselves 🔥

    Feel free to bring your...

    FREE event at Bells Mill Park in Chesapeake, VA! Come on out and enjoy the morning with fellow first responders on the same mission to be the best version of themselves 🔥

    Feel free to bring your heavy ruck or just yourself and walk with no ruck! All first responders, family, friends, and support are welcome to come out for an easy ruck at around 3 miles! Each ruck is kicked off with a thought provoking topic so that we start off the day with intentionality. Walking and talking can be a powerful tool of healing, growing, and connecting, and we take advantage of it!

    Registering for this FREE event is an RSVP!

    March 21 Responders Ruck will support the Professional Firefighters of Chesapeake at the 3rd Annual RUCK CANCER

    https://runsignup.com/Race/VA/Chesapeake/NdAnnualRUCKCancer

    3 Miles Run Walk

    Shea Dr, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • Tidewater Striders 2026 Distance Series #2 at the Dismal Swamp Canal Trail [runsignup.com]

    Sun, Feb 08, 2026 at 8:30 AM

    Description

    EVENT OVERVIEW:

    5 Mile, 10 Mile & 15 Mile Sunday, February 8, 2026 8:30AM start for everyone.

    Race Course:

    Distance Series 2 on February 8th is now at the Dismal Canal Trail, 1246 Dismal Canal Trail,...

    EVENT OVERVIEW:

    5 Mile, 10 Mile & 15 Mile Sunday, February 8, 2026 8:30AM start for everyone.

    Race Course:

    Distance Series 2 on February 8th is now at the Dismal Canal Trail, 1246 Dismal Canal Trail, Chesapeake 23322. Those running the 5 miles will go out and back 2.5 miles. Those doing the 10 miles will go out and back 5 miles. Those doing the 15 miles will go out and back 5 miles, cross the timing mats and go out 2.5 miles and turn around. Everyone will start at 8:30 and the finish line will stay open until 12:15.

    After Race Party:

    Will be at Tap It Local, 648 Grassfield Pkwy, #12, Chesapeake 23323. Just 3 1/2 miles from the race venue.

    Race Day Packet Pickup for Distance Series 2 will be at the Start/Finish line. Look for the Striders tent.

    Inclement Weather: The Race Director and the Tidewater Striders reserve the right to cancel or reschedule or adjust distances as needed in the interest of safety or access restrictions to the venue. There are no refunds but we will try and reschedule.

    Grand Prix: The 10 and 15 milers are part of the Tidewater Striders Grand Prix

    If you want to register for Distance Series 3, click here

    https://runsignup.com/tidewaterstridersdistanceseries3

    15 miler for Distance Series 2 only is a Hampton Roads Super Grand Prix

    5 Miles 10 Miles 15 Miles Run Trail Walk

    424 Albemarle Drive, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • Tidewater Striders 2026 Distance Series #3 [tidewaterstriders.com] [Register at runsignup.com]

    Sat, Feb 28, 2026 at 8:30 AM

    Description

    EVENT OVERVIEW:

    10K, 20K & 30K Saturday, February 28, 2026 8:30 AM At Dismal Swamp Canal Trail, 1246 Dismal Canal Trail, Chesapeake. There are no refunds. Everyone will start at 8:30.

    Race Courses:...

    EVENT OVERVIEW:

    10K, 20K & 30K Saturday, February 28, 2026 8:30 AM At Dismal Swamp Canal Trail, 1246 Dismal Canal Trail, Chesapeake. There are no refunds. Everyone will start at 8:30.

    Race Courses:

    Begin and finish at the entrance to the Dismal Swamp Canal Trail. 10K runners and walkers will go out to the 5K turnaround (3.1 miles) and return to the finish line. The 20K and 30K runners and walkers will go out to the 10K turnaround (6.2 miles) and return to the finish line, where the 20K participants will be done, while the 30K participants, after crossing the timing mats will go back out to the 5K turnaround and return to the finish line completing the 30K. Finish line closure is based on a 15 minute per mile and will close at 1:15. Early start, 8:15AM, for 30K walkers/slow runners ONLY may be arranged by contacting jphelanrun@gmail.com.

    After Race Parties:

    After race party is Tap It Local, 648 Grassfield Pkwy, #12, Chesapeake 23323 just 3 1/2 miles from the start/finish line in the Wal-Mart shopping center

    Directions:

    Dismal Swamp Canal Trail:, Trail Start, Old Route 17 and George Washington Hwy, Chesapeake, VA 23323 just off Rt 17. GPS tracking 1246 Dismal Canal Trail, Chesapeake, VA.

    Inclement Weather: The Race Director and the Tidewater Striders reserve the right to cancel or reschedule or adjust distances as needed in the interest of safety or access restrictions to the venue.

    Registration closes at 9:00 PM the Friday before each event. You may pick up your race number starting at 7:15 to 8:20 AM race morning at the start/finish line. Early packet pickup will be at Running Etc., Hilltop Location on Friday, February 27 starting at 4:00 to 6:00.

    Distance Series 3 20k and 30k is a Strider Running Grand Prix.

    The 10k is a walker Grand Prix.

    10k 20k 30k Run Trail Walk

    1246 Dismal Swamp Canal Trail, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • I.A.F.F. Local 2449's - 3rd Annual RUCK Cancer Walk/Run [runsignup.com]

    Sat, Mar 21, 2026 at 9:00 AM

    Description

    The Professional Fire Fighters of Chesapeake, IAFF Local 2449, cordially invite you to our 12th Annual Mustache March Madness and our 3rd Annual RUCK CANCER Walk/Run!

    PLEASE NOTE - the Event Location...

    The Professional Fire Fighters of Chesapeake, IAFF Local 2449, cordially invite you to our 12th Annual Mustache March Madness and our 3rd Annual RUCK CANCER Walk/Run!

    PLEASE NOTE - the Event Location has changed to BELLS MILL PARK in Chesapeake, VA this year!

    RUCK Registration/Packet Pickup – 07:30 (day of only)

    RUCK Start Time – 09:00

    Post-Race Cookout Ends - 13:00

    Entry Fee - $45

    Fee includes:

    • Custom RUCK Cancer Race T-shirt and Post-Ruck Cookout provided by the Kiwanis Club of Chesapeake!

    • You must register by 2/21/2026 to be guaranteed a RUCK Cancer Race T-shirt!

    RUCK Distances:

    Short – 5K

    Long – 10K

    Like a traditional RUCK, we encourage all participants to wear a ruck sack or 35 pound weighted vest. If you do not have your own RUCK, we have 35 CFD SCBA’s available to use. Please click on the link here to reserve an SCBA to use for the day!

    No RUCK/SCBA is necessary to participate though, we encourage participants to support our cause by enjoying fellowship and walking the course as well.

    1st Place Overall Male & Female of the 10K RUCK win a prize! Must be wearing a SCBA, 35-pound Weighted Vest, or 35-pound RUCK Sack

    1st Place Male and Female of the 10K RUCK wearing a 35-pound RUCK Sack win a prize!

    ABOUT THE CAUSE

    In 2014, members of the Chesapeake Fire Department and the Professional Fire Fighters of Chesapeake, Local 2449, began an annual tradition called Mustache March Madness. We sold t-shirts to support local firefighters and their family's battling cancer. Over the last 12 years, we have supported our brothers and sisters by raising money every March and donating funds to those affected throughout the year.

    In 2024, we created the RUCK Cancer Walk/Run as a creative way to exercise and raise funds for these firefighters! In the two years since we started the RUCK, we have had 437 RUCKERS participate and have donated $27,600 to 19 firefighter families across Hampton Roads!

    March 21, 2026 marks our 12th Annual Mustache March Madness and our 3rd annual RUCK Cancer Walk/Run!

    DONATIONS

    Unable to participate, but still want to contribute? Click on the "Donate" tab at the top of our race website to support our members!

    SPONSORS

    Thank you to the organizations and businesses that have sponsored us in building this event through their time, effort, and financial contributions. See their links below to learn more about these organizations committed to supporting Mustache March Madness, RUCK Cancer, and the Professional Fire Fighters of Chesapeake, Local 2449.

    Interesting in becoming a sponsor, email: iaff2449@gmail.com

    10k Run Walk

    424 Albemarle Drive, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps

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