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30 running, walking, fun run, and other events in Williamsburg, Virginia

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

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  • Terrible Twelve [ultrasignup.com]

    Sat, Aug 23, 2025

    Ultra

    Williamsburg, Virginia, United States
    OpenStreetMap Google Maps
  • Jamestown High School Swamp Run 5k [runsignup.com]

    Thu, Jan 01, 2026 at 9:00 AM

    Description

    Jamestown High School Cross Country/Track & Field is hosting the SWAMP RUN 5K on Saturday, March 8th.

    We are just having a simple race! $15.00 for students and $20.00 for adults! No T-shirts or...

    Jamestown High School Cross Country/Track & Field is hosting the SWAMP RUN 5K on Saturday, March 8th.

    We are just having a simple race! $15.00 for students and $20.00 for adults! No T-shirts or Awards - just a 5k on the trail!

    $20.00 on race day

    9:00 am - Jamestown High School Swamp Run - Colonial Runners Grand Prix Event (Proceeds - Jamestown HS XC/Track)

    No Frills Race - No T-shirts and no medals.

    The course is 100% on track, trails, and bridges.

    Jamestown High School Swamp Run 5k

    Date: Saturday, March 8th, 2025

    What: Walk or Run 5K

    Where: Jamestown High School, Williamsburg, VA

    Colonial Road Runners Grand Prix Event

    8:30 am 1-mile fun run on the track

    5k Start Time: 9:00 am

    Course: Jamestown High School Cross Country Course

    Course Map: https://www.scribblemaps.com/maps/view/JHSCC5k/JHSNEWXCCOURSE2022

    • Race Day Registration $20.00 online only – available on race day 7:15-8:30 am

    • Support Jamestown Cross Country and Track

    • Race Bib Pick up 7:15-8:45 am at the track

    • Questions: Email [email protected]

    • CRR Race Coordinator: Rick Platt 757-345-1431, Email: [email protected]

    5k Fun Run Run Trail Walk

    1350 John Tyler Hwy, Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps
  • 47th Colonial Half Marathon and 5K [colonialsportswilliamsburg.com] [Register at runsignup.com]

    Sat, Feb 14, 2026 at 8:30 AM

    Description

    The tradition continues, on February 14th, 2026 in Williamsburg, Virginia.

    Colonial Sports, Inc. invites you to test yourself in this prestigious and historical

    Half Marathon Run. Are you a Bad Ass...

    The tradition continues, on February 14th, 2026 in Williamsburg, Virginia.

    Colonial Sports, Inc. invites you to test yourself in this prestigious and historical

    Half Marathon Run. Are you a Bad Ass Runner or Walker? Prove it! Beat Fortitude Hill!

    5K Runners

    All 5K runners and walkers must be on-site NLT 8 AM. This race will start under one gun at 8:30 AM.

    The Colonial 5K Starts at 8:30 AM near the intersection of Nassau and Francis Streets adjacent to the Dewitt Wallace Art Museum in Colonial Williamsburg, follow Nassau St. to Prince George St. turn left on Prince George St, follow Prince George St. to a sharp right onto Scotland St. follow Scotland St to a right on Nassau St and then left on Prince George St. You’ll enter the historical Colonial Williamsburg, run past the Governor’s mansion and turn left on Nicholson St., then right on Waller St and take a right at the bus stop and enter the path leading past the Capitol Building and onto the Duke of Gloucester St., Run towards the Armory building around the cone on the Duke of Gloucester St. and onto the gravel path leading to Francis St, cross Francis Street and onto S. England St., right on Newport Ave., and right on Nassau and then up Fortitude Hill and to the Finish.

    5K Awards:

    Medals are awarded to the top three men and women overall, top male and female Masters and Grand Masters, top three male and female 14 and under, and then five-year age groups from 15-19 through 80 and over. Top Three Male and Female in the Competitive Walk, Top Male and Female Masters and Grand Masters in the Competitive Walk,

    5K PERKS:

    Swag bag, Long Sleeve race T (Guaranteed T and T size for those signed up by Jan 31st, 2026) , Custom Finisher medal ( Must Finish), Beer and Pizza ticket, Fife and Drum Start line Escort and music/entertainment by DJ Drew.

    Mini Half Runners

    One Wave of Runners and walkers. Mini Half participants start and finish at the start line. This is not an officially timed race.

    The Mini Half will Start at 9:30 AM following the last of the Half Marathon start. See Course Map. Runners Start on Nassau St, cross Francis takes the first right onto Duke of Gloucester St. run to a turn around point at the end of the Duke of Gloucester St. and back to Nassau, left on Nassau, cross Francis, and thru to the Finish.

    All finishing participants will receive a long Sleeve T-Shirt, Finisher’s Medal, and a free entry pass to the “Post Race Celebration” and complimentary beer. You must show ID if you're 21 or older for your complimentary beer.

    Half Marathon Runners

    All Half Marathon runners and walkers must be on-site NLT 8:45 AM. This race starts with one gun at 9:00 AM

    The Colonial Half Marathon Starts at 9:00 AM near the intersection of Nassau and Francis Streets adjacent to the Dewitt Wallace Art Museum in Colonial Williamsburg, follow Nassau St. to Prince George St. turn left on Prince George St, follow Prince George St. to a sharp right onto Scotland St. follow Scotland St to a right on Nassau St and then left on Prince George St. You’ll enter the historical Colonial Williamsburg, run past the Governor’s mansion and turn left on Nicholson St., then right on Waller St and take a right at the bus stop and enter the path leading past the Capitol Building and onto the Duke of Gloucester St., Run towards the Armory building and then turn left to cross Francis St. and onto S. England St., then pick up the traditional course (see map) running out and back on the Carters Grove Country Road. On the last leg to the finish, runners turn left off of S. England onto Newport Ave. then right on Nassau St and up Fortitude Hill, and on to the Finish. The time limit

    for the Half Marathon is 3.5 hours.

    Last opportunity to Register is Race day Feb 14th, 2026 from 7 AM to 9 AM. Location is the registration tent near the start line.

    All finishing participants will receive a long Sleeve Performance T-Shirt (Guaranteed T and T size for those signed up by Jan 31st, 2026) , Finisher’s Medal, and a free entry pass to the “Post Race Celebration” complimentary beer and pizza. You must show ID if you're 21 or older for your complimentary beer.

    Cash Awards Top 3 men and women. 1st Place $300, 2nd place $200, 3rd Place $100.

    Custom Bowl for the Top Male and Female.

    Custom Tiles for the 2nd thru 10th place overall men and women.

    Medals for the Top three men and women in Masters and Grand Masters.

    Medals for the Top 3 in the following Age Group Categories, 16 and Under, 17-19, five years increment age groups 20-24 through 75 and over.

    Both races are a Healthy Hearts! Healthy Mind! event.

    Donations can be made to:

    • Daniel G. and Rosemary B. Stimson Track Endowment at W&M: For 39 years, the Colonial Half Marathon and 5K benefited the Track and Field program at the College of William and Mary. The past success and legacy of this event are due to the guidance and leadership of the College of William and Mary’s Track and Field coaches, in particular, Coach Daniel Stimson. Coach Stimson was the College of William and Mary’s Director of Track and Field as well as the Colonial Half Marathon Race Director for 25 years. Coach Stimson passed away in Oct. of 2017.

    • Heroes on the Water (HOW) Tidewater chapter: HOW is a 501(c)(3) non-profit that provides no cost therapeutic kayak fishing experiences to veterans, first-responders, active-duty military members, and their families. Volunteer-led chapters hold regularly scheduled events that improve the lives of participants while supporting the community. The primary modality is kayak fishing, which has proven cognitive and emotional benefits. The Tidewater chapter of HOW engages with the community through local events to build greater awareness of the need for our first responders, military, and their families to have a space where they can find peace and comradery on the water.

    1.31 Miles 3.1 Miles 5k 13.1 Miles Half Marathon Run Virtual Walk

    326 West Francis St., Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps
  • Blizzard Blast 5k & 10k [bishopsevents.com] [Register at raceroster.com]

    Sat, Feb 21, 2026 at 8:30 AM

    Description

    Come & experience the scenic and relaxing ambience of the forest along the Greenspring Interpretive Trail. The trail loops through a landscape of beaver ponds, wetlands and forests, and it includes sections of wooden boardwalk as well as interpretative signs about the environment, historic events of the early colonists and American Indians and area wildlife.

    5k 10k Run

    1350 John Tyler Hwy, Williamsburg, Virginia, 23186, United States
    OpenStreetMap Google Maps
  • Viking 5K, 10K, & 13.1M at Williamsburg, VA (08) [runsignup.com]

    Sat, Feb 21, 2026 at 8:30 AM

    Description

    Race Information

    The race starts at 8:30 AM.

    Packet pickup starts 30 minutes before the race and ends 10 minutes before the race starts.

    All runners must register on RunSignup.

    No on-site...

    Race Information

    The race starts at 8:30 AM.

    Packet pickup starts 30 minutes before the race and ends 10 minutes before the race starts.

    All runners must register on RunSignup.

    No on-site registration.

    Additional Information

    The start location has changed.

    Park at the Lois Hornsby Middle School.

    5K & 10K (1.56M)

    https://www.mapmyrun.com/routes/view/6645699747

    The course is an out-and-back (3.11M)

    The 5K does the out-and-back one time.

    The 10K does the out-and-back two times.

    Half Marathon Course (1.64M)

    https://www.mapmyrun.com/routes/view/6645699496

    The course is an out-and-back (3.28M).

    The Half Marathon does the out-and-back four times.

    Course Time Limit

    3 hours and 30 minutes.

    Finisher Medals

    https://usroadrunning.com/FinisherMedals.php

    Shirt and Gear Shop

    https://usroadrunning.com/Gear.php

    Best Costume

    https://usroadrunning.com/BestCostume.php

    Series Points

    https://usroadrunning.com/S.php

    Awards

    https://usroadrunning.com/Awards.php

    Frequently Asked Questions and Information

    https://usroadrunning.com/FAQ.php

    US Road Running

    https://usroadrunning.com

    5k 10k 13.1 Miles Run

    Richmond Road, Williamsburg, Virginia, 23188, United States
    OpenStreetMap Google Maps
  • Medal Madness 5K, 10K, & 13.1M at Williamsburg, VA (10) [runsignup.com]

    Sat, Mar 07, 2026 at 8:30 AM

    Description

    Race Information

    The race starts at 8:30 AM.

    Packet pickup starts 30 minutes before the race and ends 10 minutes before the race starts.

    All runners must register on RunSignup.

    No on-site...

    Race Information

    The race starts at 8:30 AM.

    Packet pickup starts 30 minutes before the race and ends 10 minutes before the race starts.

    All runners must register on RunSignup.

    No on-site registration.

    Parking & Start Location Update

    Please park in the Lois Hornsby Middle School parking lot and follow the sidewalk to the middle school bus loop, where the race will begin.

    https://maps.app.goo.gl/MyLJQnNEWbW3inM1A

    5K & 10K Course (1.56M)

    https://www.mapmyrun.com/routes/view/6645699747

    The course is an out-and-back (3.11M)

    The 5K does the out-and-back one time.

    The 10K does the out-and-back two times.

    Half Marathon Course (1.64M)

    https://www.mapmyrun.com/routes/view/6645699496

    The course is an out-and-back (3.28M).

    The Half Marathon does the out-and-back four times.

    Course Time Limit

    3 hours and 30 minutes.

    Finisher Medals

    https://usroadrunning.com/FinisherMedals.php

    Shirt and Gear Shop

    https://usroadrunning.com/Gear.php

    Best Costume

    https://usroadrunning.com/BestCostume.php

    Series Points

    https://usroadrunning.com/S.php

    Awards

    https://usroadrunning.com/Awards.php

    Frequently Asked Questions and Information

    https://usroadrunning.com/FAQ.php

    US Road Running

    https://usroadrunning.com

    5k 10k 13.1 Miles Run Walk

    Richmond Road, Williamsburg, Virginia, 23188, United States
    OpenStreetMap Google Maps
  • Virginia Fire Chiefs Foundation 5k [runsignup.com]

    Sat, Mar 14, 2026 at 6:00 AM

    Description

    A 5k run through the historic Colonial Williamsburg. Starting at Bruton Parish Church and passing by the Historic Capitol and Governor’s Palace, you will loop through the City of Williamsburg’s municipal buildings before looping back to finish back on historic Duke of Gloucester Street.

    1 Miles 3.1 Miles 5k Run Virtual Walk

    201 W. Duke Of Gloucester Street, Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps
  • Medal Madness 5K, 10K, & 13.1M at Williamsburg, VA (12) [runsignup.com]

    Sat, Mar 21, 2026 at 8:30 AM

    Description

    Race Information

    The race starts at 8:30 AM.

    Packet pickup starts 30 minutes before the race and ends 10 minutes before the race starts.

    All runners must register on RunSignup.

    No on-site...

    Race Information

    The race starts at 8:30 AM.

    Packet pickup starts 30 minutes before the race and ends 10 minutes before the race starts.

    All runners must register on RunSignup.

    No on-site registration.

    Parking & Start Location Update

    Please Park in the Lois Hornsby Middle School parking lot and follow the sidewalk to the middle school bus loop, where the race will begin.

    https://maps.app.goo.gl/MyLJQnNEWbW3inM1A

    5K & 10K (1.56M)

    https://www.mapmyrun.com/routes/view/6645699747

    The course is an out-and-back (3.11M)

    The 5K does the out-and-back one time.

    The 10K does the out-and-back two times.

    Half Marathon Course (1.64M)

    https://www.mapmyrun.com/routes/view/6645699496

    The course is an out-and-back (3.28M).

    The Half Marathon does the out-and-back four times.

    Course Time Limit

    3 hours and 30 minutes.

    Finisher Medals

    https://usroadrunning.com/FinisherMedals.php

    Shirt and Gear Shop

    https://usroadrunning.com/Gear.php

    Best Costume

    https://usroadrunning.com/BestCostume.php

    Series Points

    https://usroadrunning.com/S.php

    Awards

    https://usroadrunning.com/Awards.php

    Frequently Asked Questions and Information

    https://usroadrunning.com/FAQ.php

    US Road Running

    https://usroadrunning.com

    5k 10k 13.1 Miles Run Walk

    Richmond Road, Williamsburg, Virginia, 23188, United States
    OpenStreetMap Google Maps
  • Bike the Bridge [runsignup.com] [Register at runsignup.com]

    Sat, Apr 04, 2026 at 8:00 AM

    Description

    Join James City County Parks & Recreation in the sixth annual Bike the Bridge event taking place Saturday, April 4 from 8 a.m. - 1 p.m. The route will start in James City County, cross the...

    Join James City County Parks & Recreation in the sixth annual Bike the Bridge event taking place Saturday, April 4 from 8 a.m. - 1 p.m. The route will start in James City County, cross the Chickahominy River and enter into Charles City County along the Virginia Capital Trail. Routes options include 15, 25 and 50 miles. Parking, rider check-in and lunch will be located at Jamestown Beach Event Park, 2205 Jamestown Rd, Williamsburg, VA 23185. Light refreshments, event t-shirt and lunch are included with rider registration.

    50-Mile Route Check In: 8-9 a.m.

    25-Mile Route Check In: 8:30-9:30 a.m.

    15-Mile Route Check In: 9:30-10 a.m.

    *There are no bike restrictions for this ride, however, please abide by the Virginia Capital Trail rules and regulations which can be found here: www.virginiacapitaltrail.org/trail-rules

    50 Miles Cycling Trail

    2205 Jamestown Rd, Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps
  • 17th Annual Run The D.O.G. St. 5K [runsignup.com]

    Sat, Apr 18, 2026 at 7:00 AM

    Description

    "A Healthy Heart, Healthy Mind Event"

    Colonial Road Runners Grand Prix

    Hampton Roads Super Grand Prix

    USATF Certified 5K Race Palace Green Course certification pending.

    RACE SCHEDULE

    Friday, Apr. 17,...

    "A Healthy Heart, Healthy Mind Event"

    Colonial Road Runners Grand Prix

    Hampton Roads Super Grand Prix

    USATF Certified 5K Race Palace Green Course certification pending.

    RACE SCHEDULE

    Friday, Apr. 17, 2026

    12 PM - 6 PM // Early Packet Pickup and Final Registration

    Colonial Sports

    1303 Jamestown Road #111

    Williamsburg, VA. 23185

    Saturday, Apr. 18, 2026 (RACE DAY)

    NO Race Day Registration!

    • Race Day Packet Pickup at the START LINE 6:30 AM – 7:30 AM

    • Start Line is on Prince George St. between Nassau St. and Henry St. (This year closer to Nassau St.)

    • Two Shilling Mile begins at 7:00 AM at the Finish Line on Duke of Gloucester St.

    • 5K Run/Run Walk/Competitive Walk Begins at 7:30 AM

    START: The race starts on Prince George St. (the Start line is in front of Nassau St.) runs through Williamsburg and Colonial Williamsburg ending on Duke of Gloucester St. Runners will pass the Governor's Palace and the Colonial Capitol building before finishing the final 800 meters on the most famous street in America, the Duke of Gloucester Street.

    Age groups begin at 8 & under, 9-10, 11-12, 13-15, 16-19, then 5 year increments extending to 80 and over.

    FINISH: The Finish is on Duke of Gloucester St. (D.O.G. St.) just before Nassau St.

    AWARDS: Top three overall men and women receive Cash award of $200 1st Place, $100 2nd Place, $50 3rd Place plus a custom medal. Top three finishers in each age group receive a custom medal. 1st Place Male and Female Masters receive a cash award of $50.00. Top three male and female masters (age 40+) receive a custom medal. 1st Place Male and Female walker receive a cash award of $50.00. Top three male and female walkers receive a custom medal. Three Team awards: Fastest Team, Largest Team and Largest Donation. Winning teams receive custom plaque. Two Shilling Mile and 5K finishers receive a custom finisher medal. Tech tee race shirt given to all 5K participants signed up by Wednesday, April 8th, 2026. Custom Race T and T shirt size ordered only guaranteed to those registered by Apr 8th, 2026

    1 Miles 3.1 Miles 5k 3.10686 Miles Run Walk

    Duke Of Gloucester Street, Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps
  • Revolutionary BBQ Brawl 5k & Fun Run [runsignup.com]

    Sun, Apr 26, 2026 at 9:40 AM

    Description

    This will be the final event of the Revolutionary BBQ Brawl held April 24-26th 2026 at Chickahominy Riverfront Park. Come race a NEW local favorite course through the park, along the James, and on...

    This will be the final event of the Revolutionary BBQ Brawl held April 24-26th 2026 at Chickahominy Riverfront Park. Come race a NEW local favorite course through the park, along the James, and on the VCT. There will be both a 1-mile fun run and 5k race. The 5k Race is a Colonial Road Runner Grand Prix event. All proceeds benefit Culturefix. Culturefix strives to improve Greater Williamsburg’s cultural offerings for residents and visitors, by enhancing arts infrastructure; developing and promoting the arts and culture industry; and by creating a wide array of arts and cultural events.

    1 Miles 5k Fun Run Run

    1350 John Tyler Hwy, Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps
  • Hike for Hospice House [runsignup.com]

    Sat, May 02, 2026 at 9:00 AM

    Description

    Since 2013, Hospice House of Williamsburg has raised over $700,000 through its annual Hike for Hospice House. Hospice House of Williamsburg offers care, comfort, and compassion through and beyond end...

    Since 2013, Hospice House of Williamsburg has raised over $700,000 through its annual Hike for Hospice House. Hospice House of Williamsburg offers care, comfort, and compassion through and beyond end of life as well as bereavement support to all free of charge. Funding raised through events like Hike for Hospice House ensures that all service to guests and their loved ones can remain cost-free and that Hospice House can remain a vital and accessible resource to serve the Williamsburg community and beyond.

    At this year's Hike for Hospice House, we celebrate life by walking one mile through Colonial Williamsburg followed by a memorial program, activities for the whole family, and special ways to remember the lives of our loved ones, all raising funds in support of this important community resource. We hope you'll join us as we join together as a community to remember the lives that touched ours.

    Each ticket includes a t-shirt (with preferred size guaranteed only to sign-ups prior to April 20. On the day of the race, we will have extras of all sizes available on a first come, first served basis). Assorted snacks and water bottles will also be provided. Children 12 and under are FREE, and there is a reduced price for middle, high school, and college students age 13-23.

    1 Miles Walk

    326 W Francis Street, Williamsburg, Virginia, 23188, United States
    OpenStreetMap Google Maps
  • Virginia Regional Ballet 5K Run/Walk, 1 Mile Fun Run/Walk [dancevrb.com] [Register at runsignup.com]

    Sat, May 09, 2026 at 8:00 AM

    Description

    Race Day Registration begins at 7:30 am

    Virginia Regional Ballet, Inc., a 501(c)(3) nonprofit organization, and the Colonial Road Runners announce the 9th annual 5K in Williamsburg, on a...

    Race Day Registration begins at 7:30 am

    Virginia Regional Ballet, Inc., a 501(c)(3) nonprofit organization, and the Colonial Road Runners announce the 9th annual 5K in Williamsburg, on a counterclockwise loop of the beautiful tree-lined First Colony neighborhood, 125 Pasbehegh Drive. This is a Colonial Road Runners Grand Prix Event. The purpose of this popular event is to raise funds for a live orchestra for Virginia Regional Ballet’s annual production of The Nutcracker ballet at Ferguson Center for the Arts, Newport News, in December. The family-friendly 5K event begins at 8:00 a.m. with a 1 mile Fun Run/Walk, and at 8:30 a.m. the 5K begins, with awards and refreshments following in the First Colony Pavilion.

    1 Miles 5k Fun Run Run Walk

    Williamsburg, Virginia, 23185, United States
    OpenStreetMap Google Maps

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