2026 Calendar

2026
JAN-MAR

Jan 3 – New Year 5k, 10k & 13.1M Run, Williamsburg VA

Jan 4 – Snowy Owl 10m Trail Run/Hike, Williamsburg VA

Jan 10 – New Year 5k, 10k Run, Midlothian VA

Jan 17 – Beaverdam Park “Full Hike”, 9m self-guided, Gloucester VA

Jan 17 – Chills In The Mill: Harwoods Half Marathon & 5K, Williamsburg VA

Jan 24 – Schock & Shivers 5k & Cold Water Challenge, Chesapeake VA

Jan 25 – Final Gravity Brewing Frostbite 15k, Lewis Ginter Gardens, Henrico VA

Feb 7 – Viking 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA

Feb 15 – Indian Fields Tavern Half Marathon, Quarter Marathon & 5k, Charles City VA

Feb 21 – Beaverdam Park “Full Hike”, 9m self-guided, Gloucester VA

Feb 27-Mar 1 – One City Marathon Weekend, Newport News VA

Mar 14 – Gloucester Ed Foundation 3k & 8k, Gloucester VA

Mar 14 – Virginia Fire Chiefs Foundation 5k, Williamsburg VA

Mar 21 – Ashland Railroad 5k & 10k Run, Ashland VA

Mar 22 – The Hill Topper 5k, Church Hill, Richmond VA

Mar 28 – RIverwatch on the Piakatank, Gloucester VA

Mar 28-29 – Women’s Trail Festival, Williamsburg VA

Mar 29 – Daffodil Dash 5k, Gloucester VA

2026
APR-JUN

Apr 4 – Sheetz-to-Sheetz Trail Run, King George VA

Apr 12 – Wildstride Race Series: 10k, Half Marathon, Williamsburg VA

Apr 18 – Ukrop’s Monument Ave 10k, Richmond VA

May 2 – Luau 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA

May 8-9 – Cap2Cap Bicycle Ride, Virginia Capital Trail VA

May 9 – Williamsburg Winery 5k/ 10k, Williamsburg VA

May 9 – Down River Rip 4.4M River Swim, Midlothian VA

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

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 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

2026
JUL-SEP

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 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

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