Trail Running calendar near Matoaca 2026-2027

A low key, mostly trail half marathon at York River State Park on June 7, 2026, run in a no frills Hike a Half format. The course includes single track, fire roads and about one mile of pavement, with aid stations and finisher medals.

Fox Trot 5k and 1 Mile at Merrie Mill Farm and Vineyard in Keswick on June 7, 2026 features a cross-country course, post-race cabana for participants, and a raffle with a gift basket valued at least $200.

A single-track trail race behind Zehmer Hall in Charlottesville covering about 3.1 miles, with steep climbs, technical footing, timing and bibs, and prizes for top finishers.

A Backyard Ultra at Loch Lothian in Midlothian, VA where runners repeat a 4.14 mile loop each hour until one remains; the event supports Semper Fi and America's Fund and awards a cash prize plus the Sword of Honor.

A three-race summer trail series at Sandy Bottom Nature Park organized by the Peninsula Track Club, featuring 5K, 4-mile, and 5-mile events plus a full-series entry and awards across age groups and walker categories.

An evening trail event on the High Bridge Trail with 5k, Half Marathon, and 50k courses starting at Camp Paradise; the 50k features multiple aid stations, pacer allowances on the back half, and a course cutoff at Prospect.

A cumulative event pairing Night Train and Freight Train at High Bridge Trail State Park with multiple combined-distance options and a $15 Challenge fee that supports trail maintenance. Finish both distances in the same year to earn a uniqu..

A mud-run fundraiser in King George, VA on June 27, 2026, featuring a 4-mile obstacle course and a 1-mile kids run, organized by the Dahlgren Lions Club with team awards by group size.

Night Owl 9k at Freedom Park in Williamsburg VA is a night trail race over single track, fire road and paved trails with rolling hills and technical sections. Post race activities include pizza, beer and wildlife education.

A manually timed trail event at Windsor Castle Park in Smithfield, VA, run on a 3.1-mile loop with 10 hour, 5 hour, 2 hour and a one-lap 5k formats; aid station and rucking options are available.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

Family friendly 5K mud run at Virginia Motorsports Park in Richmond with obstacles, waist deep mud pits, a pre party and an after party with music and food. Standard and VIP registration options are available.

A half marathon and a 50K on the Dahlgren Railroad Heritage Trail in King George, VA on August 8, 2026. Mostly flat rails to trails courses with time limits, finisher medals, apparel options and postrace food including free MooThru ice crea..

A 12 hour endurance run at Oak Grove Lake Park in Chesapeake, VA, made of repeated laps of a 1.5 mile loop. The unpaved, tree lined course features lake and forest views and is limited to 60 runners.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

A community 5K and 10K at Fifty-Third Winery & Vineyard in Louisa, Virginia that raises funds for Hooves & Paws Animal Rescue. The event offers in-person races and several virtual entry options with medal and shirt choices.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

Trail runs of 10 and 5 miles at Powhatan State Park during the Pawpaw festival, featuring riverside singletrack, open-field views, a water station near mile 5, festival amenities, and park lodging options.

Run the Rock | Rockville is the fourth annual 5K at Luck Stone’s Rockville quarry near Richmond, featuring gravel terrain, quarry views, local food vendors, family activities, swag, and raffles supporting a charitable cause.