Trail Running calendar near Williamsburg 2026-2027

Kick off the New Year with a no frills 5K or 8K along the Capital Trail in Williamsburg. Low cost entry supports CRR scholarship funds and the friendly post race vibe includes coffee and doughnuts.

Run the Snowy Owl 10 mile trail at York River State Park on Jan 4, 2026 to support AWARE, with live owls and scenic technical single track and fast fire roads. All finishers receive a ceramic medal and race winter hat.

Take on the Sandy Bottom 8 hour Training Run at Sandy Bottom Nature Park, with timed or untimed options on a fast, flat 5 km loop through scenic trails. Bring your own hydration and enjoy homemade medals, swag, and a welcoming park vibe.

Run scenic trails at Harwoods Mill Park in Yorktown, VA on January 17, 2026 with a Half Marathon or 5K option. Limited fields, aid stations, and post race shirts make this a chilly January favorite for trail lovers.

Enjoy a fast, scenic half marathon along the flat Dahlgren Railroad Heritage Trail in King George, VA on Jan 31, 2026. Cupless racing with SpeedCup options, aid stations, and a custom finisher medal support the local trail.

Take on the Swammie Shuffle 200, a more than 200 mile self supported coastal ultra starting at Sandbridge with 5.5 days to finish, passing lighthouses and Corolla wild horses. Limited spots and proceeds benefit veterans.

Discover scenic trails around Saint Marys Lake near Leonardtown, MD with 17K, 34K or 50K on one to three laps through Salem Forest. Limited to 100 runners, this intimate event has rugged single track, lake views and on course aid.

Run coast to coast along North Carolina's Outer Banks from Corolla to Hatteras, enjoying fully paved roads and sweeping coastal views. Choose 100 mile, 100K, or a 100 mile relay and celebrate at The Wreck Tiki Bar finish.

Celebrate trail running at the Women's Trail Festival in Freedom Park, Williamsburg on March 28 and 29, 2026. Enjoy races, classes, a T shirt and lunch while supporting local charities and connecting with a welcoming women focused community..

Relaxed 14 mile point to point run along the scenic Dahlgren Railroad Heritage Trail in Virginia with gentle elevation. Quirky aid stations serve pie, s'mores and pretzels and finishers receive practical swag while supporting local charitie..

Run the scenic Long Creek 60K or 30K at First Landing State Park in Virginia Beach through maritime forest, cypress swamp and beach shoreline. The 30K is one loop, the 60K two loops, with aid stations and a reusable SpeedCup.

Run a scenic, flat 5k along the Virginia Capital Trail by the James River at Rocketts Landing in Richmond. Choose in person or virtual entry, enjoy chip timing, a tech race shirt and finisher medal, with live results posted after the race.

Enjoy a no frills, community focused trail half marathon through scenic York River State Park near Williamsburg. Limited to 250 runners, this rolling single track course serves up rugged terrain and a tough final two miles plus a PR coaster..

Pick your challenge on a scenic 3.1 mile loop at Windsor Castle Park with timed 10 hour, 5 hour and 2 hour options plus a one lap 5k and rucking available. Enjoy a low key vibe, a well stocked aid station and a homemade finisher medal.

Run to the Taproom at Creekside Farm Brewery in King George offers 5K and 8K trail runs through a scenic farm along the Rappahannock River. Finish with live music, food trucks and a complimentary beer for participants 21 and over.

Join the Howlin' Coyote Canicross Trail Race in King George VA for a scenic, dog friendly trail run that benefits Friends of Caledon State Park. Enjoy varied terrain, reusable speedCups and the chance to race with your leashed pup.

Take on scenic new trails at Pocahontas State Park with a chip timed half marathon or 10K. Expect runnable singletrack, on course water stations, live results and race day age group awards in a festive park setting.

Run a scenic 50K two loop course at First Landing State Park in Virginia Beach on December 13, 2026, with aid stations and a lively finish. Finishers get a Brooks shirt and medal and can celebrate at a brewery party.