Trail Running calendar near Keswick 2026-2027

A night trail event at Prince William Forest Park with a 25+ mile loop run twice to form a 50+ mile race. The course is mainly single track, features staffed aid stations, and has specific crew and pacer rules.

A community 5K and 1 mile Fun Run in Warrenton, VA that raises funds for Fauquier Education Farm, a 501(c)(3) that advances agricultural education and donates its harvest to local food banks.

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.

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.

A roughly 50 km trail ultramarathon on the southern Massanutten range with about 5,700 feet of elevation gain, six aid stations, and a post run gathering at the Route 211 commuter parking lot. Entry is limited to 75 runners.

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.

Locust Shade 5k and 10k on July 25, 2026 uses shaded scenic trails at Locust Shade Park in Triangle VA. Walkers are welcome and virtual entries are available with medal and shirt options.

A summer trail event in Crozet, VA listed as a 30 Miler with about 29.0 miles and 7,610 feet of climbing. The steep gravel out-and-back laps include limited aid, shuttle parking, and rugged summer conditions.

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 memorial trail run in the Jefferson National Forest featuring a roughly 60 km course and a 50 km Party Route option, three aid stations, limited entry, and a largely unmarked route supported by a GPX file and turnsheet.

A 3.1 miles obstacle course through Thomas Jefferson’s Poplar Forest with elite, team, corporate and non-competitive waves. Entry fees support Poplar Forest education and elite competitors must complete all obstacles to qualify for prizes.

A trail race at Bull Run Marina on August 15, 2026 offering 5K and 10K distances plus several virtual entry options. The route follows the Bull Run Occoquan Trail and registration uses tiered fees that include mandatory charges.

A community road event at Leopold's Preserve in Broad Run on August 23, 2026 offering 5 km and 10 km on-course races plus virtual options with medal and shirt choices. The race is part of the Sippin Series with Farm Brewery at Broad Run and..

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 5K and 10K cross country style race at Albemarle CiderWorks on August 30, 2026, with virtual entry options and post-race cider available at the venue.

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 clockwise 71-mile circuit of the orange-blazed Massanutten Trail around Fort Valley, VA, with 13,500 ft of elevation change, scheduled aid stations, strict qualifications and enforced cut-offs; GPX and aid charts are provided.