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DEC 5

Chesapeake Rotary Holly Jolly Jog Race and Fun Run presented by the YMCA of South Hampton Roads

Chesapeake, VA
Ever wanted to race your friends, family and neighbors down Battlefield Blvd? Well, the Holly Jolly Jog is back for a 3rd year! A family-friendly, 1 mile fun run and race before the Chesapeake Rotary Christmas Parade will give you the chance to do exactly that. 30 minutes before the start of the Christmas parade, lace up and run, jog, or walk the route - under the lights - and being cheered on by thousands of your Chesapeake friends and family. Add to the festivities with Christmas lights, pjs, ugly sweaters and costumes (no full Santa costumes allowed - there’s only one Santa in the parade). Also, sadly, for safety reasons, no farm animals will be allowed to race this year. The course will be chip-timed and feature an official USTAF measurement. Are you registering your whole family? We have a family registration package where you can register 2 adults and up to 4 children for $75. Click Family Registration after you click the sign-up link above to add additional registrants.
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DEC 6

Tidewater Strider Dismal Swamp 50K / Marathon /Half Marathon/50K Relay

Chesapeake, VA
Welcome to the 7th Annual Dismal Swamp /50K/Marathon/Half Marathon and 50k Relay Marathon will take place on our USATF Certified Course! Ranked the Fastest course in Virginia and 47th Fastest in the US by Findmymarathon.com! Huge BQ opportunity! 50K & Half Marathon courses are also on a Certfied course COURSE: The 50k & Relay Starts at 7:00 am & Marathon/Half Marathon starts at 7:30 am. There is a 9hr limit (4 PM). The course is an out and back 3.88 miles each way for the 50k. There are 4 loops for 50k. The Marathon course is a Certified BQ Course, it's 6.55 up 6.55 back 2 loops for the Marathon & one Loop for the Half Marathon. very fast course! The 50k and Marathon/Half Marathon courses are USATF Certified. FLUIDS AND FOOD: 1 full aid station at start/finish after every loop with food, water, and nutrition drinks! This year, due to the marathon& Half Marathon, there will be water stations set up on the course where the Marathon runners will hit 9 times & Half 4 times during the race. The manned stations will only be set up during the Marathon! We will leave an unmanned water station set up close to the 50k turnaround for the Ultra race when the Marathon is complete. AMENITIES & POST-RACE: Finishers receive a Medal, Hoodie Sweatshirt for 50K, and long-sleeve shirt for Marathon & Half Marathon and Finishers items. All Runners who qualify for Boston will receive a BQ Shirt! New this Year, we will have a Beer Garden from 9 am-2 pm. Those of you who finish after the Beer Garden is closed will be able to redeem your two drinks at Garage Brewery until next weekend. We can only keep the Beer Garden open for a certain amount of time. We will also have Pizza to enjoy! TIME LIMITS: The 50K & 50K Relay Starts at 7 am & Full Marathon & Half Marathon starts at 7:30 AM -- Finish line will close at 4 PM. AWARDS: The top three males and Females overall and the top three males and females in the following Age groups: 39 and under/40-49/50-59 /60 and over will receive awards for the 50K! The top three males and Females overall and the top three males and females in 10-year age groups will also receive awards In the Marathon & Half REGISTRATION: Registration will be open race day up to the Race Start STRIDER PLUS/LEGACY RUNNERS: A Discount will be applied at checkout. CLUB MEMBERSHIP DISCOUNTS: A Club membership discount of $5.00 is available up thru race day. 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. PACKET PICKUP: Pre-race day Packet Pick will be at Running etc VB Saturday, December 5th, from 1-3 p.m., &Race day packet pick up will be at the start line starting at 6:15 am until the Marathon & half Marathon start! 50K RELAY: When registering, please signup your team if you are the 1st member signing up. Other members, please use the same team name. You can have anywhere from 2 to 4 members on your team! ELITE FIELD: 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 Orangerunning@yahoo.com! We will also have Nutrition drop tables set up in multiple areas on the course for the marathon. Marathon MEN: 2:40 Women 3:00 50K Men:3:15 Women: 3:50 Half Marathon Men 1:15 Women 1:22
Half Marathonrelay
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DEC 26

Kwanzaa 5k Run & Walk

Chesapeake, VA
Celebrating Unity, Culture, Community & Wellness Join Harambe Inc. for the Kwanzaa 5K Walk & Run, a community celebration bringing people together through fitness, culture, and the spirit of unity! Held on the first day of Kwanzaa, this family-friendly event celebrates the seven principles of Kwanzaa: Unity, Self-Determination, Collective Work and Responsibility, Cooperative Economics, Purpose, Creativity, and Faith. Whether you're an experienced runner, a casual walker, or participating in your first 5K, everyone is welcome! All registered participants will receive a custom Kwanzaa 5K T-shirt and a commemorative finisher medal! Running for a Cause Proceeds from the Kwanzaa 5K will support the Harambe Creative Futures Scholarship, a program dedicated to making arts education accessible to children and teenagers, regardless of their family's financial circumstances. Through this initiative, Harambe Inc. aims to help young people explore their creativity, develop their talents, and access opportunities in the arts. Event Highlights 5K run and walk for all fitness levelsCustom Kwanzaa 5K T-shirtCustom commemorative finisher medalCelebration of Kwanzaa's seven principlesFamily-friendly atmosphereSupporting arts education for local youth Date: Saturday, December 26, 2026 Location: Oak Grove Lake Park, Chesapeake VA Come run, walk, and celebrate the spirit of Umoja (Unity) while helping create brighter futures for young artists! Organized by Harambe Inc., a federally recognized nonprofit organization.
5K
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JAN 9

Tidewater Striders 2027 Distance Series #1

Chesapeake, VA
Welcome to the Tidewater Striders Distance Series 2027! Prepare for an unforgettable experience with our 3-race challenge bundle, offering a unique opportunity to test your limits across three diverse distances. We introduced the shorter distances last year and the were such a hit that we continued for 2027 making the event even more appealing to runners of all levels. Sign up for any of the three challenges and not only will you be taking part in a fantastic running experience, but you'll also receive a special commemorative medal as a reward for your dedication! Remember, to claim your medal, you must successfully complete all three events within each chosen challenge. For those seeking a challenging yet achievable goal, we present the 10K Challenge. Please note that these distances are not part of the Striders Grand Prix. To participate, you will Run/Walk a 5K for Distance Series 1 at the scenic Dismal Canal Trail. Then, gear up for Distance Series 2 at Fort Monroe with a Run/Walk of 5 Miles. Finally, complete the 10K for Distance Series 3 at the Dismal Canal Trail. For runners aiming for a slightly longer distance, the Half Marathon Challenge is designed for you! Distance Series 2 and 3 are part of the Striders Grand Prix. To participate in this challenge, you will Run/Walk a 10K for Distance Series 1 at the beautiful Dismal Canal Trail. Then, brace yourselves for Distance Series 2 at Fort Monroe with a Run/Walk of 10 miles. Distance Series 3 you will walk/run a 20K For those aiming for our longest distances, our Marathon Challenge is for you. You'll walk or run a 20K (12.4 miles) at the scenic Dismal Swamp Canal, followed by walking or running 15 miles at the beautiful Fort Monroe and culminating with a 30K (18.6) mile walk or run back at the Dismal Swamp Canal. The Fort Monroe 15-miler is also designated as a Hampton Roads Super Grand Prix event. If you would like to sign up for DS2, click here: https://runsignup.com/tidewaterstridersdistanceseries2 If you would like to sign up for DS3, click here: https://runsignup.com/tidewaterstridersdistanceseries3 Exciting news! This years premium is a long sleeve technical shirt that we will be offering at the low price of $10.00. Orders will be placed after Distance Series 1 but will not be available for pickup until Distance Series 3 on February 27. Register before October 10th to enjoy the lowest rates Packet pickup will be the Friday before each event from 4 to 6 PM at Running Etc. Hilltop location and race morning from 7:15 AM to 8:20 AM.
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JAN 16

Cookie Classic Run

Chesapeake, VA
It's our 13th Annual Cookie Classic Run! January 16th, 2027, Saturday 9am 1246 Dismal Swamp Canal Trail This multi-distance family friendly run/walk event is a great way to launch the 2027 cookie season & start runners off on their 2027 running year! All distances are out and back, on flat asphalt at Chesapeake's Dismal Swamp Canal Trail, with Girl Scout Cookies waiting for you at the finish! Whether you're an experienced runner or just starting out, this is the perfect opportunity to challenge yourself, meet new people, and have fun! All abilities welcomed. We can't wait to see you at the starting line! Distance Categories: 1 mile, 5k, 10k Virtual Run – “Do-Si-Don't Show” Challenge – “Conquering The Cookie” Run Perks: Box of Cookies - Register by 10/16/2026 for guaranteed selection of a box of cookies provided after you’ve completed your distance in personRace Shirt - Register by 11/1/2026 for guaranteed T-shirt sizing Chipped timing Photos - Access to professional photographs (digital images available at no fee)Digital Finisher certificatesAll 1 mile runners Receive Commemorative PatchAll 5k & 10k runners Receive Finisher Swag & Medal5k Age Placement Awards10k Age Placement Awards DJ & Warm Up SessionDo-Si-Don't Show Virtual Runners receive the finisher gift(s), medal, T-shirt & race bib delivered by post. (Virtual does not receive a box of cookies.)Conquering the Cookie Event Series: Earn Bling Finisher Gift by completing challenge running events. This is a 2-part in-person only run challenge; Runners complete 1 distance in Chesapeake VA then 1 distance in Troutville VA) Course Support: 5k Water Stations10k Water & Gatorade StationStart/ Finish Porta-potties Keep in Mind: Cookie box choice & T-shirt size are not guaranteed and subject to availability on a first come, first serve basis or until quantities last if not registered by guaranteed deadline dates listed. Quantity updates and availabilities are provided at registration. Please note Pets or Comfort Animals of any kind are not permitted on course unless they are ADA-compliant certified service animals. The Cookie Classic Run is a celebration of Girl Scouts, Girl Scout families, and those who support the Girl Scout mission of building Girls of Courage, Confidence, and Character who make the world a better place! For questions, please contact the Cookie Classic Committee at: cookieclassic5k@gmail.com Sign Up Today and Join the Fun!
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JAN 23

Schock & Shivers 5k and Cold Water Challenge

Chesapeake, VA
It time to get cold! The 2027 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 Oak Grove Park on January 23, 2027, 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 Timothy Schock Memorial Lake. 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
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FEB 27

Tidewater Striders 2027 Distance Series #3

Chesapeake, VA
EVENT OVERVIEW: 10K, 20K & 30K Saturday, February 27, 2027 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:, 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 26 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.
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MAR 6

Knights of Columbus Run for Life 5K

Chesapeake, VA
On March 6, 2027, the Knights of Columbus will host a 5K Race/Walk to benefit the Crisis Pregnancy Center. Proceeds from this fundraiser will help the Center continue providing compassionate support and resources to families before, during, and after pregnancy. Funds raised will also contribute toward the purchase of a new ultrasound machine, an essential tool that enables the Center to offer critical prenatal services and life-affirming care to expectant mothers. Participants in the event will not only enjoy a day of fitness and fellowship but will also help strengthen support for mothers, babies, and families throughout our community.
5K
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