2026-27 Calendar

2026
APR-JUN

May 16 – Tour de Chesapeake – MOC Club Event

Learn More & Register. Join us for this family-friendly cycling event located in Mathews County, on Virginia’s Middle Peninsula – now in its 27th year. The supported ride is all day on Saturday, but we hope you will make a weekend of it and see all Mathews has to offer. We have lined up a whole assortment of things for you to do on Friday, Saturday and Sunday too!

May 23 – Chick-fil-A 10k/ 5k Running of the Cows, Newport News VA

May 25 – Yorktown Freedom Run 8K, 5k, Yorktown VA

Jun 6 – Boxer Brief 5k & Virtual Run, Richmond VA

Jun 7 – Bright Futures Fun(d) 1M Run, Warsaw VA

Jun 7 – Taskinas Creek Half Marathon, York River State Park, Williamsburg VA

Jun 16 – Trailzilla Fast 5K, Sandy Bottom Nature Park, Hampton VA

Jun 20 – Chesty Puller Memorial Twin Bridge 10k, West Point VA

Jun 27 – Islander Regatta – MOC Club Event

Learn More & Register. Annual 9 mile paddling event for non-motorized craft, circumnavigating one of Virginia’s few inhabited islands: Gwynn’s Island in Mathews County. With its origins as a fun summer challenge for a group of friends, the Islander Regatta is opening its door to more participants. Max 200.

Jun 27 – VA Super Tri – Adult, Kids, Relay Triathon, Midlothian VA

Jun 28 – High Bridge Gravel Bike Time Trial, Richmond VA

Jun 30 – Trailzilla Feel Good 4-Miler, Sandy Bottom Nature Park, Hampton VA

2026
JUL-SEP

Jul 4 – Mathews VA250 1.776m Walk/ Run, Put-In-Creek Park/Pavilion in Historic Mathews County

More Information – FREE local event where you can learn about state and local history THEN enjoy post-event food & music in Mathews Virginia. Sponsored by Mathews VA250 committee & supported by our local Daughters of the American Revolution (DAR) and Sons of the American Revolutions (SAR) chapters and the Mathews Outdoor Club, this FREE event will kick off your Independence Celebration in Mathews style.

Jul 4-25 – Le Tour de Couch Potato® FREE virtual cycling event

Cycle 100 miles in 23 days. A virtual cycling event for novice and experienced riders that coincides with Le Tour de France. Multi-national and free – for 15+ years and going strong.

Jul 4 – Eagle 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA

Jul 4 – Deltaville 5k & Kids Fun Run, Deltaville VA

Jul 11 – Windsor Castle 10-Hour, Smithfield VA

Jul 19 – Cal Tri Olympic, Sprint & Youth Sprint Triathlon, Williamsburg VA

Aug 1 – Ninja 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA

Aug 2 – Guts Gravel Glory (GGG) 50m Bike Race, Chesterfield VA

Aug 15 – Wharf to Wharf (W2W) Swim – MOC Club Event

Learn More & Register. In collaboration with Mathews Land Conservancy, the W2W is a one-mile open water swim in the East River, where you can complete the distance with or without swim aids. Post-swim breakfast under the pavilion at Williams Wharf is provided by Mathews Land Conservancy. W2W is a tribute to the late L. Wayne Hudgins who was a Mathews native, Williams Wharf enthusiast and long-time member of the Mathews Land Conservancy’s board.

Aug 29 – Pints and Paws 5k, Williamsburg VA

Sep 12 – Patriots Triathlon, Williamsburg VA

Sep 20 – Robious Landing Triathlon, Chesterfield VA

Sep 26 – FREE VA Boating Safety Course, Volunteer Rescue Squad Bldg, Mathews VA

Sep 27 – Fiends Frenzy 5k, Busch Gardens, Williamsburg VA

2026
OCT-DEC

Oct 3 – Haunted 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA

Oct 3 – Go Forward Together Bike Ride, Final Gravity Brewing, Richmond VA

Oct 3 – Maplewood Mile 5k – Run for the Trees, Richmond VA

Oct 4 – Pocahontas Trail Festival – 10k & Half Marathon, Chesterfield VA

Oct 10 – Fall Foliage Adventure Race, Jamestown VA

Oct 17 – Mathews Marathon, Half Marathon & Relay – MOC Club Event

Learn More & Register. Celebrating our 6th year in 2026, the “World’s Flattest Race Course” provides options for a full & half marathon, 5-person relay or virtual participation. Included in the cost of the race is a pre-race Carbo Load pasta dinner on Friday, courtesy of Mathews Family YMCA and Mathews Womens Giving Circle. Enjoy the quiet backroads, beaches, zero hills & small town racing in rural tidewater Virginia.

Oct 25 – Regency Mile (formerly Short Pump Mile), Richmond VA

Nov 7 – Gobbler 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA

Nov 14 – Richmond Marathon, Half Marathon & 8k, Richmond VA

Nov 26 – Blue Talon Bistro Turkey Trot, Colonial Williamsburg VA

Nov 26 – Richmond Turkey Trot 5k, Richmond VA

Dec 6 – Christmas Town Dash 8k, Busch Gardens, Williamsburg VA

2027
JAN-MAR

Apr 3 – Gwynn’s Island Raw Bar Run – The Hatchery x MOC Club Event

Learn More & Register. Located at historic Callis Wharf, the Gwynn’s Island 5k Race hugs the island coastline for a stunning out-and-back route, and features the post-race celebration hosted at Oyster Seed Holding. Join us for the unique road race and post-event celebration with Live Music, Drinks and Food featuring The Hatchery food service.