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19 running events in Chesapeake, Virginia

From big races to Saturday morning group runs—find running 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
  • Cookie Classic 2026 [gsccc.org] [Register at runsignup.com]

    Sat, Jan 17, 2026 at 8:00 AM

    Description

    We are back again! Celebrating! our 12th Annual Cookie Classic Run. We welcome participants of ALL Abilities to join us for this run/jog/walk family friendly event as we launch the 2026 cookie season...

    We are back again! Celebrating! our 12th Annual Cookie Classic Run. We welcome participants of ALL Abilities to join us for this run/jog/walk family friendly event as we launch the 2026 cookie season and as runners kick off for their 2026 race season! **

    All distances are out and back, on the flat and fast asphalt at Chesapeake's Dismal Swamp Canal Trail, with Girl Scout Cookies waiting for you at the finish!

    • Participant Categories: 1miler, 5k (3.1miles), 10k (6.2miles) , Do-Si-Don't Show Virtual Run

    • NEW NEW NEW: CONQUERING THE COOKIE - Event Series offering new exploration & fun outdoorsFEATURES:

    • By 10/15/2025: guaranteed choice of FULL-SIZED box of cookies provided ONLY after finishing at finish line **

    • By 11/1/2025: guaranteed choice of T-shirt sizing ** AND name within design on the back of the T-shirt

    • In-person Event Chesapeake, VA: chipped timing AND access to professional photographs (digital images available free of charge) &finisher certificates

    • 1milers: patch finisher gift

    • 5K and 10K (Surprise) finisher gift

    • 5k and 10k Age placed Awards

    • New: Conquering the Cookie Event Series: finisher gift

    • (only available for in person event participation -1 event distance in Chesapeake, 1 event distance in Trouteville)
    • Do-Si-Don't Show Virtual Runners will NOT receive box of cookies however they will receive the finisher gift(s), medal, Tshirt & racebib which will be mailed on 1/16/26 or 1/17/26

    The Cookie Classic Run is a celebration of Girl Scouts, Girl Scout families, and all who support the Girl Scout mission of building girls of courage, confidence and character who make the world a better place!

    **registrations after deadline dates listed above: cookie choice and Tshirt sizing availability is on a first come, first serve basis and until quantities run out. YOU WILL have access to see quantity availability during the registration process.

    ***We kindly acknowledge and inform participants that 4 legged family/friend are not permitted unless they are certified service animals.

    For questions, please contact the race team at [email protected]

    1 Miles 5k 10k Run Virtual

    1246 Dismal Swamp Canal Trail, 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
  • Schock & Shivers 5k and Cold Water Challenge [runsignup.com]

    Sat, Feb 21, 2026 at 9:00 AM

    Description

    It time to get cold! The 2026 the Schock & Shivers 5k and Cold Water Challenge is a Team Chesapeake Law Enforcement United event to fundraise for the Road to Hope. Join us at the Oak Grove Lake Park...

    It time to get cold! The 2026 the Schock & Shivers 5k and Cold Water Challenge is a Team Chesapeake Law Enforcement United event to fundraise for the Road to Hope. Join us at the Oak Grove Lake Park on January 24, 2026, where we will honor Chesapeake officers Tim Schock and Jarrod Shivers, who were killed in the line of duty. This race will warm up your body while running, and give you a chance to cool off at the end - by taking the Cold Water Challenge in the Oak Grove Lake Park. Chesapeake Police and Fire divers will be there for your safety through out event!

    Read about why we do what we do, and get to know Tim and Jarrod: https://www.odmp.org/agency/643-chesapeake-police-department-virginia

    WHO WE ARE

    Team Chesapeake is part of the larger Law Enforcement United, a 501c3 that fundraises annually for the Road to Hope, a 250-mile bike ride to honor the fallen and remember the survivors. We also fundraise for COPS Kids Camp, the Officer Down Memorial Page, and Spirit of Blue. Visit us at www.leunited.org

    5k Run

    Chesapeake, Virginia, 23320, 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 [email protected].

    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: [email protected]

    10k Run Walk

    424 Albemarle Drive, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • 2026 Autism Society Superheroes vs Villains [runsignup.com]

    Sat, Apr 11, 2026 at 8:15 AM

    Description

    Join us for the Superheroes vs Villains 5K taking place in the Great Dismal Swamp, a unique event that combines the beauty of nature with a powerful cause. This race supports our mission to improve...

    Join us for the Superheroes vs Villains 5K taking place in the Great Dismal Swamp, a unique event that combines the beauty of nature with a powerful cause. This race supports our mission to improve the lives of individuals affected by Autism, focusing on maximizing self-sufficiency, independence, and quality of life for those living with Autism. Run, walk, or volunteer to help us create a positive impact and raise awareness for the Autism community. Together, we can make a difference—one step at a time.

    1 Miles 5k Run Walk

    1246 Dismal Swamp Canal Trail, Chesapeake, Virginia, 23323, United States
    OpenStreetMap Google Maps
  • Striders Dismal Swamp 5 Miler and Kid's 1 Mile [runsignup.com]

    Sat, Apr 25, 2026 at 8:00 AM

    Description

    Welcome to the Striders Spring Festival

    Dismal swamp 5 Miler and 1 miler

    COURSE: This is a 2.5-mile out and 2.5-mile back course on the closed 2-lane roadway at the Dismal Swamp Trail Park in...

    Welcome to the Striders Spring Festival

    Dismal swamp 5 Miler and 1 miler

    COURSE: This is a 2.5-mile out and 2.5-mile back course on the closed 2-lane roadway at the Dismal Swamp Trail Park in Chesapeake. One Miler is .5 miles out and back. 1 mile is an up-and-back on the Trail

    PACKET PICKUP: Early Packet Pick will be at Point 2 Running Company, Chesapeake, on Friday, April 24th, from 3-6 pm! Race day pick-up will start at 7 am

    FLUIDS AND FOOD: There will be 1 aid station with water. The aid station location will be at 2.5 miles.

    AMENITIES & POST-RACE: T-Shirts will be provided. Onsite hospitality & refreshments

    TIME LIMITS: 5MILER--- The race starts at 8:00 AM! The finish line will close at 10:30. One mile starts at 9:30 a.m.

    AWARDS: Top 3 overall Males and Females and the top 3 males and females in 10-year age groups will receive awards for the 5-mile race! 1-mile awards top 3 overall males and females and top 3 males and females in the following age 6&under, 7-8 9-10 11-12 13 & up

    REGISTRATION: Registration will be open until, 9PM April 24th 2026.

    STRIDER PLUS/LEGACY RUNNERS: Automatically applied at checkout thru April 24th.

    CLUB MEMBERSHIP DISCOUNTS: A Club membership discount of $5.00 is available up thru April 25th. Discounts are automatically applied on the payment page during registration. You should use the account you used to register for the club to apply for this discount. We will also attempt to match on name/date of birth.

    Paper entry forms are not available.

    This is a Strider Grand Prix & Youth Grand Prix

    1 Miles 5 Miles Run Trail

    1246 Dismal Swamp Canal Trail, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • Tidewater Strider Marathon and Half Marathon Spring Edition [runsignup.com]

    Sun, Apr 26, 2026 at 7:00 AM

    Description

    Welcome to the Tidewater Striders Marathon and Half Marathon Home to one of the Flattest and fastest Marathons in the country and the Fastest in Virginia!!!!

    Website Find my Marathon rates The...

    Welcome to the Tidewater Striders Marathon and Half Marathon Home to one of the Flattest and fastest Marathons in the country and the Fastest in Virginia!!!!

    Website Find my Marathon rates The Tidewater Strider Marathon as the 52nd fastest Marathon in the Country and the Fastest Marathon in Virginia! This marathon ranked 37th in 2025 for BQ percentage in the country https://findmymarathon.com/race-detail.php?zname=Tidewater%20Strider%20Marathon

    In 2021, the Tidewater Strider BQ invitational and the Strider Marathon both ran on the same course and were ranked #2 and #35 in the country for their Boston Qualifying percentages!

    COURSE: This is a Marathon and Half Marathon course on the closed 2-lane roadway at the Dismal Swamp Trail Park in Chesapeake. The full Marathon course will be USATF Certified course and that means its a Boston Qualifying race

    PACKET PICKUP: Early Packet pick-up will be at Point 2 running company in Chesapeake Friday, April 24th from 3-6pm! Race day pick-up will be from 6:15 -7:30 am!

    FLUIDS AND FOOD: There will be 4 aid stations with water for the half Marathon and 9 water stations for the full.

    AMENITIES & POST-RACE: Finishers receive a Medal and Premium Long Sleeve Shirt. Onsite hospitality & refreshments. Post-race party onsite!

    TIME LIMITS: The Full Marathon will start at 7 am and Half Marathon will start at 7:30 AM! The finish line will close at 1:30 PM. Walkers may arrange an early start or self-time after 1:30 PM.

    AWARDS: Top 3 overall Males and Females and top 3 overall Masters Male & Female the top 3 males and females in 10-year age groups will receive awards!

    REGISTRATION: Registration will be open until April 24th, 2026.

    LEGACY RUNNERS/STRIDERS PLUS: Discounts available thru April 25th.

    CLUB MEMBERSHIP DISCOUNTS: A Club membership discount of $5.00 is available up thru April 24th. Discounts are automatically applied on the payment page during registration. You should use the account you used to register for the club to apply for this discount. We will also attempt to match on name/date of birth.

    Paper entry forms are not available.

    ELITE FIELD: Back this year we will have an Elite Entry for this year's Race: to receive a Comp Elite Entry, you had to have run faster than the time listed below in the last 2 years! If you would like to claim the entry, contact Thomas [email protected]! We will also have Prize Money for the top 3 Males & Females in the Marathon & Top Males & Females in the Half! We will also have Nutrition drop tables set up in multiple areas of the course.

    Marathon

    MEN: 2:40

    Women 3:00

    Half Marathon

    Men 1:15

    Women 1:23

    Strider Spring Running Festival Challenge is Back - Run the Dismal Swamp 5 Miler on Saturday and the Half or the Full on Sunday to receive a challenge Medal!

    Snake Challenge- 5 miler & Half Marathon

    Bear Challenge- 5 miler & Full Marathon

    13.1 Miles 26.2 Miles Half Marathon Run Trail Walk

    1246 Dismal Swamp Canal Trail, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • Anchor Scholarship Foundation 5K and FunRun [runsignup.com]

    Sat, May 16, 2026 at 7:00 AM

    Description

    Come out and help support Surface Navy Families but running this flat out and back 5k at Dismal Swamp. This race also supports the Navy Surface Line Week, points will be given to command with the most participants and fastest runner.

    5k Run

    1246 Dismal Swamp Canal Trail, Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps
  • Strider XC Classic [runsignup.com]

    Sat, May 16, 2026 at 7:30 AM

    Description

    REGISTRATION IS NOW OPEN

    This is a Tidewater Strider Grand Prix Race, Tidewater Striders Youth Grand Prix Race, Hampton Roads Super Grand Prix Race.

    The 1st 150 Registered Participants Guaranteed...

    REGISTRATION IS NOW OPEN

    This is a Tidewater Strider Grand Prix Race, Tidewater Striders Youth Grand Prix Race, Hampton Roads Super Grand Prix Race.

    The 1st 150 Registered Participants Guaranteed Shirts.

    COURSE: This is a 5K XC course at Bells Mill Park in Chesapeake. 1.5-mile course for the Kids classic

    FLUIDS AND FOOD: There will be 1 aid station with water and replacement drink.

    AMENITIES & POST-RACE: Awesome T-shirts for the first 150 5K and Kids Race participants and medals for all Finishers. Guaranteed T-shirt sizes until April 24, 2026. There is a NO Shirt option available as well with $3.00 off discount. Runners and walkers are welcome to join us for an afterparty at Bells Mill Park for refreshments, including a variety of lemonade, fruit punch, and a catered Panera lunch box. This is subject to availability and boxes will be available until they run out. One lunch box per participant with their bib. Unfortunately, we cannot accommodate spectators with lunch boxes.

    TIME LIMITS: The Kid's race starts at 7:30.

    The 5K race starts at 8:15 AM.

    The finish line will close at 10 am.

    REGISTRATION: Race day registration is available starting at 6:30 AM until 20 minutes before the start of each race. No Exceptions

    STRIDER PLUS/LEGACY RUNNERS: Your discount will automatically apply at checkout.

    CLUB MEMBERSHIP DISCOUNTS: A Club membership discount of $5.00 is available up thru May 16th. Discounts are automatically applied on the payment page during registration. You should use the account you used to register for the club to apply for this discount. We will also attempt to match on name/date of birth.

    AWARDS:5K Awards will be given to the top 3 Male & Female open and master runners. Age group awards will be 12 &under 13-19- & 10-year age groups until 70&over. Awards for the Strider kids' classic are as follows 6 &under,7-8,9-10, 11-12, 13-17 M&F. Awards will be given out at the end of the 5K race. Walking Awards top 3 Male & Female.

    Competitive Walking Division: If you register in the Competitive walking Division you must walk the entire race to be eligible for awards in this division if run you will be moved to the 5K Run division!

    1.5 Miles 5k Run Walk

    Chesapeake, Virginia, 23322, United States
    OpenStreetMap Google Maps

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