Trail Running calendar near Keswick 2026-2027

A lakeside trail race at Boar's Head Resort in Charlottesville on July 11, 2026, featuring a 5.2 mile loop with about 745 feet of elevation change. The race is open to runners and walkers and is part of the Summer Trail Running Series.

A roughly 50 km trail run on the Massanutten range with 5,700 feet of climb, six aid stations (two water only), varied terrain and scenic overlooks, finishing with a post-run gathering at the Route 211 commuter lot.

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.

Muddy Dash Richmond on July 25, 2026 at Virginia Motorsports Park is a non-competitive 5K with obstacles, mud pits, and on-site Pre-Party and After-Party festivities. Family-friendly registration options include value and VIP packages.

A July trail event at Locust Shade Park in Triangle, VA offering 5K and 10K distances plus multiple virtual options. The courses run on shaded, scenic trails and walkers are welcome.

A rugged 29.0 mile looped event in Crozet, Virginia on August 1, 2026, featuring five steep gravel laps and about 7,610 ft of elevation gain and loss. Entry is limited to 65 runners with a small fee and a waitlist.

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 6K cross country race beginning and ending at Death Ridge Brewery, using parts of the Verdun Adventure Bound course. The event features varied trails, ponds and bridged streams, race shirts for early registrants, and awards with proceeds..

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.

In-person 5K and 10K races run along the Bull Run Occoquan Trail at Bull Run Marina in Clifton, VA on August 15, 2026; virtual entries are available with different medal and shirt options and fees vary by registration period.

A community running event at Leopold’s Preserve in Broad Run, VA on August 23, 2026 offering 5 km and 10 km races plus virtual options with medal and shirt choices; part of the Sippin Series with the Farm Brewery at Broad Run.

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 5 km and 10 km running event at Albemarle CiderWorks in North Garden, VA on August 30, 2026, with a cross-country course introduced for 2025 and both in-person and virtual entry options including medal and shirt choices.

The 53rd Winery 5K and 10K on September 5, 2026 takes place at Fifty-Third Winery & Vineyard in Louisa, Virginia. The event includes 5K, 10K and virtual options and benefits Hooves & Paws Animal Rescue.

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.

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.

Trail races at Douthat State Park featuring a roughly 13-mile loop used for a 50K, marathon, half marathon, and a six-mile race, with multiple aid stations, loop-based finisher rules, and limited field sizes.

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.

A community running event in Farmville on September 12, 2026 offering in-person and virtual 5K and 10K races plus hand cycle divisions on a flat, crushed gravel out-and-back course along the High Bridge State Park Trail.