Regional Race Calendar
2026
OCT-DEC
Oct 10 – River Ride 2026, Kilmarnock 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. Registration closes 10/10 OR if we reach our Max of 500.
Oct 17 – Beaverdam Park: The Full Hike, Gloucester VA
Oct 17 – Beaverdam Park: Fall Foliage Paddle, Gloucester VA
Oct 24 – Jamestown Half Marathon & 5k, Williamsburg VA
Oct 25 – Regency Mile (formerly Short Pump Mile), Jamestown VA
Oct 31 – River & Bay 5k, VIMS at Gloucester Point VA
Nov 7 – Beaverdam Park: Naturalist Paddle, Gloucester VA
Nov 7 – Gobbler 5k, 10k & Half Marathon, Freedom Park, Williamsburg VA
Nov 14 – Richmond Marathon, Half Marathon & 8k, Richmond VA
Nov 21 – Beaverdam Park: The Full Hike, Gloucester 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.
