10 events in Williamsburg, Virginia

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

• Capital Color Ride [runsignup.com]
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  Sat, Jun 06, 2026 at 9:00 AM

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  Join James City County Parks & Recreation in the Capital Color Ride event. The route will include a 15-mile stretch along the Virginia Capital Trail. Full route and color stop information will be...

  Join James City County Parks & Recreation in the Capital Color Ride event. The route will include a 15-mile stretch along the Virginia Capital Trail. Full route and color stop information will be available closer to the race date, however, starting and ending location will be at Chickahominy Riverfront Park. Light refreshments, t-shirt, and lunch are included in rider registration.

  Three start times are available at 9 a.m., 9:30 a.m. and 10 a.m.to stagger volume of traffic at the color stops along the way--be sure to select a stage during registration.

  *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

  15 Miles Cycling Trail

  1350 John Tyler Hwy, Williamsburg, Virginia, 23185, United States
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• Jamestown Triathlon [kineticmultisports.com] [Register at runsignup.com]
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  Sun, Jun 07, 2026 at 7:00 AM

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  Just minutes from historic Williamsburg, VA and next door to the original Jamestown Settlement, the Jamestown Triathlon is a great mid-season race. The swim takes place at beautiful Jamestown beach...

  Just minutes from historic Williamsburg, VA and next door to the original Jamestown Settlement, the Jamestown Triathlon is a great mid-season race. The swim takes place at beautiful Jamestown beach where you can watch Osprey catch their breakfast or see a pod of dolphins swim along the course. The bike course is flat, fast and parallels the Cap-Cap bike trail along Rt. 5. The run course is simply amazing as it winds through historic farmland and forest on a combination of bike paths and jogging trails. Be sure to stay for the weekend to experience all that the greater Williamsburg area has to offer, including the new Billsburg Brewery, the Jamestown Settlement and so much MORE.

  ***The Jamestown Sprint & Olympic Triathlons are the USA Triathlon Virginia State Championships.

  Qualifying for the Toyota Age Group National Championships. State Championships will qualify the top 35% or top five (5) finishers in an age group (whichever is greater). You may only qualify for Olympic-distance Nationals by placing in the Olympic distance State Championship race or Sprint Nationals by placing in the sprint distance State Championship race.

  High School State Championships Exemption: All high school athletes who finish any of the State High School Championships will automatically qualify for Sprint-distance (pending they are at least age 15 as of December 31, 2025)

  Any state championship that occurs after June 1, 2025 will qualify for BOTH 2025 AND 2026 Toyota Age Group Nationals. The qualification criteria for 2025 Age Group Nationals are subject to change from what it is for 2025. Click here to review the full 2023 qualification criteria for Toyota Age Group Nationals.

  Athletes do not have to be a resident of a state to win that state’s championship. Any age group athlete competing in an age group division is eligible to win any state championship.

  Run Swim Trail Triathlon

  2205 Jamestown Rd, Williamsburg, Virginia, 23185, United States
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• 2026 Cal Tri Williamsburg - 7.19.26 [runsignup.com]
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  Sun, Jul 19, 2026 at 8:00 AM

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  2026 Cal Tri Williamsburg - 7.19.26. Our triathlon returns to the shores of Jamestown Beach Park in historic Williamsburg. Flat and fast featuring the run primarily on the Virginia Capital Trail.

  18...

  2026 Cal Tri Williamsburg - 7.19.26. Our triathlon returns to the shores of Jamestown Beach Park in historic Williamsburg. Flat and fast featuring the run primarily on the Virginia Capital Trail.

  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. Colonial Williamsburg. Historic Jamestowne. Busch Gardens Williamsburg.

  AIRPORT. Newport News/Williamsburg (PHF)

  AIR TEMPERATURE (AVG). 73 F / 89 F

  WATER TEMPERATURE (AVG). 83 F. Use the 20% CALTRI2025 discount code at blueseventy. Note: Fusion wetsuits not eligible for discount.

  Aquabike Cycling Duathlon Run Swim SwimRun Trail Triathlon

  Williamsburg, Virginia, 23185, United States
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• Patriots Triathlon [kineticmultisports.com] [Register at runsignup.com]
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  Sat, Sep 12, 2026 at 7:00 AM

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  The Patriots Triathlon is a great end of season race with Olympic and Sprint options all while being just minutes from historic Williamsburg, VA and the Jamestown Settlement. The swim takes place at...

  The Patriots Triathlon is a great end of season race with Olympic and Sprint options all while being just minutes from historic Williamsburg, VA and the Jamestown Settlement. The swim takes place at beautiful Jamestown beach where you can watch Osprey catch their breakfast or see a pod of dolphins swim along the course. The bike course is flat, fast and parallels the Cap-Cap bike trail along Rt. 5. The run course is simply amazing as it winds through historic farmland and forest on a combination of bike paths and jogging trails. Be sure to stay for the weekend to experience all that the greater Williamsburg area has to offer!

  Not sure if you should register? Well, check out these videos from the Patriots Triathlon HERE, then sign up below!

  For further race details go to https://kineticmultisports.com/races/patriots/.

  Run Swim Trail Triathlon

  2205 Jamestown Rd, Williamsburg, Virginia, 23185, United States
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• 8th Annual Weighted Angels 5k Run & Walk [weightedangels.com] [Register at runsignup.com]
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  Sun, Sep 27, 2026 at 9:00 AM

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  Weighted Angels is a 501(c)3 non-profit organization operating out of the Virginia Peninsula. We provide weighted stuffed animals to grieving families who have experienced stillbirth and infant loss...

  Weighted Angels is a 501(c)3 non-profit organization operating out of the Virginia Peninsula. We provide weighted stuffed animals to grieving families who have experienced stillbirth and infant loss before they leave the hospital. Our mission is to make sure no family leaves the hospital with empty arms.

  Did you know the fastest 5k ever run was completed by Joshua Cheptegei in 12 minutes and 35 seconds? With the current rate of stillbirth being 1 every 16 seconds, that means in just that short time, an average of 47 babies were born silently into this world. The current statistics are alarming and heart breaking. These families need our support now more than ever.

  Join us for the Weighted Angels 5K to raise awareness, walk/run in remembrance and honor of our loved ones, and raise funds to help us better serve the pregnancy, stillbirth, and infant loss families of Virginia. Your support and participation will help bring awareness during October Infant & Pregnancy Loss Awareness Month. Participants can run/walk in person or virtually this year. We would love to have you join us!

  Post your pre and post-race pictures on Facebook and Instagram! Tag @weightedangels #weightedangels5k #weightedangels #nomoreemptyarms

  PACKET PICK-UP

  Day of Race Registration & Packet Pick-Up

  Sunday, September 27, 2026 | 8:00am-9:55am

  Billsburg Brewery

  2054 Jamestown Road

  Williamsburg, VA 23185

  • Day of Race Registration is allowed but the price increases to $45.00 and a T-Shirt and race entry is not guaranteed.

  • There will be a pause in all registrations and packet pick-up from 9:00am-9:15am during our Memorial Service.

  RACE SCHEDULE

  Memorial Service | 9:00am

  1 Mile Zoo Fun Run | 9:30am

  5k Run & Walk | 10:00am

  Award Ceremony | 11:30am

  ENTRY FEES

  5k

  Early Bird 5K In Person through 6/30/2026 | $30

  5K In Person through 07/1/2026-09/20/2026 | $35

  5K Week of In Person through 09/21/2026-09/24/2026 I $40 (No online registration after 09/24/2026)

  Day of Registration for 5k 09/27/2026 I $45

  1 Mile Fun Run

  Early Bird 1 Mile Zoo Fun Run Registration through 06/30/2026 I $15

  1 Mile Zoo Fun Run Registration beginning 07/1/2026-09/20/2026| $20

  1 Mile Zoo Fun Run Week of Registration 09/21/2026-09/24/2026 I $25 (No online registration after 09/24/2026)

  Day of Registration for 1 Mile Zoo Fun Run 09/27/2026 ( no guarantee of fun run bag) I $30

  *ONLINE RACE REGISTRATION WILL CLOSE ON 09/24/2026 at midnight.

  **REGISTRATION MUST BE RECEIVED BY 08/31/2026 FOR A T-SHIRT GUARANTEE.

  COURSE

  Flat and very fast 5K course, starting and finishing on the service road at the beginning of the Virginia Capital Trail, doing a loop within the scenic, shaded Landfall at Jamestown neighborhood, with an out-and-back of Landfall Drive, and returning via Robert Fenton and the service road parallel to Jamestown Road. The one mile fun run is an out-and-back of the service road paralleling Jamestown Road.

  CREATE A TEAM FUNDRAISER

  Create a team to honor the memory and celebrate the lives of a loved one. Have your team fundraise for Weighted Angels through the day of the 5k. The top three fundraising teams will be recognized at the event.

  1 MILE ZOO FUN RUN

  Kids can dress up in their favorite zoo animal attire for this fun race! The run will be an out-and-back 1 mile run.

  AWARDS

  Cash prizes to top three overall men and women. Awards to the top three in five-year age groups (from 14-and-under through 70-and-over), and to the top three men and women in the walk division. Please note that awards are only offered for in-person runners.

  MEMORIAL SERVICE

  Please join us before the race event for a loving service that will recognize the sweet babies that have left us too soon. Submit a name under the registration section to be read aloud during the service.

  HONOR YOUR ANGEL

  Honor your angel by having their name on the back of ALL of the race t-shirts.

  Must be summited by 08/31/2026 to guarantee name is on the race shirts.

  *This event is pet and stroller friendly- all pets must be on a leash and please remember to clean up after them! If your child is riding in a stroller, they don't need a registration unless you want them to get a medal and race bag. Please email if you would like them to receive a kid friendly bag.( regular 5k price applies for the 5k run/walk).

  1 Miles 5k Fun Run Run Trail Virtual Walk

  Williamsburg, Virginia, 23185, United States
  OpenStreetMap Google Maps
• 2026 Grove Trotter 5K/10K Bridge Run at Chickahominy Riverfront Park [runsignup.com]
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  Sat, Oct 10, 2026 at 9:00 AM

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  Stretch your running legs and support Grove Christian Outreach Center at the 5th annual Grove Trotter 5K/10K. The event will be held Saturday, October 11, 2025 taking off from Chickahominy Riverfront...

  Stretch your running legs and support Grove Christian Outreach Center at the 5th annual Grove Trotter 5K/10K. The event will be held Saturday, October 11, 2025 taking off from Chickahominy Riverfront Park. The run will start out going over the Chickahominy River Bridge, out on the Capital Trail and then back in to the park for a full 5K or 10K. The entire run will take place on the well maintained Capital Trail. This is a Colonial Road Runners Grand Prix event, and awards will be given for various age groups.

  The Grove Trotter 5K/10K Bridge Run is a fundraising event to support Grove Christian Outreach Center. The Outreach Center is a 501(c)3 nonprofit organization providing food, clothing and financial assistance for impoverished families in the Grove community located in lower James City County. Please visit our website www.groveoutreach.com to learn more about our mission.

  5k 10k Run Trail

  1350 John Tyler Hwy, Williamsburg, Virginia, 23185, United States
  OpenStreetMap Google Maps
• Bikes & Beers Williamsburg [bikesandbeers.com] [Register at runsignup.com]
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  Sat, Oct 17, 2026 at 8:00 AM

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  Register for Virginia's Premier Bike Ride & Beer Festival 2026! BIKES & BEERS Cycling Event Series is coming to BILLSBURG BREWERY for 4th Annual Bike Ride & Beer Event! Ride a 15, 30, or 45-mile...

  Register for Virginia's Premier Bike Ride & Beer Festival 2026! BIKES & BEERS Cycling Event Series is coming to BILLSBURG BREWERY for 4th Annual Bike Ride & Beer Event! Ride a 15, 30, or 45-mile route through the beautiful area of Williamsburg, Virginia followed by a post-ride Beer Festival! Bikes & Beers WILLIAMSBURG is the Richmond area's premier cycling event departing from BILLSBURG BREWERY and traveling the beautiful roads and trails of Williamsburg, Virginia. All rides feature morning fuel stations, marked routes, GPS turn-by-turn instruction, rest stops, refreshments, ride marshals, and SAG support. Finish back at BILLSBURG BREWERY for a beer festival atmosphere of rewarding craft beers, live music, a charity raffle & much more!

  This is a ride for everyone - All riding levels are welcome!

  WHAT IS BIKES & BEERS:

  • Pick your ride distance and create a team of friends & family (optional)

  • Mark your calendar for a fun day of cycling and craft beer!

  • Pre Ride:

  • Check-in a half hour before your start time

  • We'll provide parking & further ride info in email instructions

  • Enjoy free coffee & fresh pastries

  • Local bike shops offering last-minute tune-ups

  • The Ride:

  • Ride your distance with ride leaders

  • Fully marked routes & GPS turn-by-turn instructions

  • Mechanical support vehicle

  • Rest stops with snacks & refreshments

  • Post Ride:

  • It's time to enjoy (2) complimentary beers on us!

  • Official co-branded Bikes & Beers Pint Glass for every rider

  • Bikes & Beers high-quality neoprene koozies

  • Enjoy the food trucks, live music, games

  • Check out our Bikes & Beers merch tent & snack stand

  • Live raffle with $3,000+ in prizes!

  • Join & Post your photos on our Facebook Page

  • Keep in touch with your newly made cycling friends!

  *Further event information will be communicated in emails after registration and in the days and weeks leading up to event day!

  WHAT YOU'LL GET:

  • Official Bikes & Beers X BILLSBURG BREWERY 2026 Pint Glass

  • (2) BILLSBURG Craft Beers are ON US!

  • High-Quality Neoprene Beer Koozies

  • Raffle Ticket with a Chance to WIN PRIZES!

  • Collectible Bike Plate - Event Photos!

  • Unique Pretzels & Athletic Non-Alcoholic Beer

  • Entry into the Post-Ride Party with LIVE MUSIC, RAFFLE, GAMES, FOOD TRUCKS & MORE!

  NEW TO OUR 2026 EVENTS:

  • PROFESSIONAL PHOTOGRAPHERS - At least (3) photographers will be snapping pics of your Bikes & Beers experience pre-ride, during the ride, and post-ride! We have amazing photo ops!

  • NON-ALCOHOLIC BEER OPTIONS - Still want to ride with us but don't want the alcohol? We now have Athletic Brewing sponsoring all our events! Looks for the blue tent and cooler full of flavorful non-alcoholic brews!

  • COLLECTABLE BIKE PLATES - At check-in, you'll receive a collectible event wristband and bike plate designed just for this event! They look awesome!

  • SPONSOR SNACKS & GIVEAWAYS - Morning coffee, fresh pastries, post-ride pretzel necklaces, recovery protein & much more!

  IT'S A CELEBRATION OF CYCLING AND CRAFT BEER!

  Riders will also receive a free raffle ticket for a chance to win brand new bikes and a ton of other prizes including a private brewery tour and cycling gear!

  Benefitting our charity partners to help improve the cycling conditions in your area. Have fun, and give back!

  15 Miles 30 Miles 45 Miles Cycling Trail

  2205 Jamestown Rd, Williamsburg, Virginia, 23185, United States
  OpenStreetMap Google Maps
• JLHR Jingle Jog 1 Mile Fun Run/Walk & 5k Run/Walk [jlhr.org] [Register at runsignup.com]
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  Sat, Dec 19, 2026 at 9:30 AM

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  Join us for the Annual JLHR Jingle Jog 1 Mile Family Fun Run & 5k Race hosted by the Junior League of Hampton Roads! The event will take place on December 19, 2026, beginning at 9:30 AM with the...

  Join us for the Annual JLHR Jingle Jog 1 Mile Family Fun Run & 5k Race hosted by the Junior League of Hampton Roads! The event will take place on December 19, 2026, beginning at 9:30 AM with the one-mile fun run and followed by the 5K beginning at 10:00 AM. Day of event registration at the race will be priced at $45.00 for the 5k and $25.00 for the 1 Mile Fun Run. The event will begin at Billsburg Brewery in Williamsburg, VA and will be an out-and-back race on the Virginia Capitol Trailhead.

  REGISTRATION WINDOWS

  Registration with guaranteed t-shirt: through 12/4 at 5:00 PM

  Pre-Registration: through 12/16 at midnight

  Day-of-Race Registration: 8:00 AM- 9:30 AM

  SWAG

  Participants of the 5k race will receive a beer ticket (21 and older, only), swag bag, t-shirt, and more! Shirt availability and size selection is only guaranteed for registrations received by 5PM on December 4th. JLHR will make efforts to honor shirt availability and selection after this date if possible.

  RACE PACKET PICK-UP

  Participants will be able to pick up their race packets beginning at 8:00 AM on race day (12/19).

  OUR MISSION

  The Junior League of Hampton Roads, Incorporated (JLHR) is an organization of women whose mission is to advance women’s leadership for meaningful community impact through volunteer action, collaboration, and training. Its purpose is exclusively educational and charitable.

  ABOUT US

  For over 65 years, the JLHR has been training our members to become community leaders through our mission-based programs that better the lives of women and families in the Hampton Roads community. Our all-volunteer leadership and workforce are able to triple the impact of our donors' dollars, which are used to train leaders, contribute to the future success of our community, and make real-time improvements to Hampton Roads.

  1 Miles 5k Fun Run Run Trail Walk

  Williamsburg, Virginia, 23185, United States
  OpenStreetMap Google Maps

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