2026-27 Calendar

2026
JUL-SEP

Aug 29 – Pints and Paws 5k, Williamsburg VA

Sep 5 – 9/11 25th Anniversary Memorial Run, Mathews VA

Sep 12 – Patriots Triathlon, Williamsburg VA

Sep 20 – Robious Landing Triathlon, Chesterfield VA

Sep 26 – Guinea Jubilee 5k, Gloucester County 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 10 – Frightening 4 mile Trail Run/Hike, York River Park, Willliamsburg VA

Oct 10 – STAR’s Candy Crawl 5k & Boo Dash, Newport News 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), Jamestown 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

Nov 28 – Irvington’s Friendly Backyard Ultra, Rappahannock Westminster Canterbury, Irvington, VA. For more information or to sign up please email Albert Pollard Jr at pollard.albert@gmail.com

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

2027
JAN-MAR

Jan 3 – Snowy Owl 10m Trail Run/ Hike, York River State Park, Williamsburg VA

Jan 16 – Chills In The Mill: Harwoods Half Marathon & 5K, Yorktown VA

2027
APR-JUN

Apr TBD – 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.

May 15 – 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 28th 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 29 – Chick-fil-A 10/5k, Newport News VA

Jun 26 – 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.

2027
JUL-SEP

Aug 14 – Wharf to Wharf (W2W) Swim – MOC Club Event

Learn More & Register. Continuing the tradition started by Mobjack Rowing (MRA) & Mathews Land Conservancy (MLC), the W2W is a one-mile open water swim in the East River. Participants can complete the distance with or without swim aids, then enjoy a post-swim breakfast provided by Mathews Family YMCA. W2W is a tribute to the late L. Wayne Hudgins and Mimi Ulsaker, who were W2W and Williams Wharf enthusiasts.