Trail Running calendar near Woodstock 2026-2027

A just under 50 km trail run in the southern Massanutten range with about 5,700 ft of elevation change, six aid stations, and a start and finish at the Route 211 parking area. 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.

A vineyard run at 868 Estate Vineyards in Purcellville, VA on July 25, 2026 offering 5k and 10k routes plus virtual entry options and tiered registration fees.

Experience the twisty single track and scenic farm fields of Germantown at this trail running event. Participants can choose between two distances while supporting local non profits in Montgomery County.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in Georgetown for the Christmas in July 5k and Half. Participants can choose between two race distances or join virtually from any location.

A community trail event on July 25, 2026 at Locust Shade Park in Triangle VA offering 5K and 10K races plus virtual entries with medal or shirt options. Walkers are welcome and entry fees vary by registration period.

Trail races at Little Bennett Regional Park on August 1, 2026 feature a 3.7 mile 5K plus and a 6.2 mile 10K on twisty singletrack with hills and streamside sections. Staging is near the Prescott Horse Trailer Area in Clarksburg Maryland.

A small, early August looped event in Crozet, VA featuring five steep gravel laps totaling 29.0 miles and about 7,610 ft of elevation gain, limited entry, basic aid, and shuttle parking.

A race day at Third Winchester Battlefield on August 8, 2026 offering 5K, 10K, and half marathon distances plus virtual options and tiered registration fees; walkers are welcome and courses pass through battlefield scenery.

A remote trail event on routes near the Wild Oak Trail, held on a roughly 60 km course with a 50 km party option. The route has about 8,000 feet of climbing, limited aid stations, minimal course markings, and a restricted field size.

Ridge Reaper 5k & 10k takes place on August 15, 2026 at Bull Run Marina in Clifton, VA, using the Bull Run Occoquan Trail. The event offers 5 km and 10 km in-person races plus several virtual entry options with medals and shirts.

Experience the MCRRC Groovin Woodstock 7K XC at the Woodstock Equestrian Center in Maryland. This low key cross country race offers a scenic 7 km route for club members and non members alike.

A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, offering in-person and virtual options and included in 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.

Trail-style 5K and 10K at Dirt Farm Brewing in Bluemont, VA on August 29, 2026, featuring rugged terrain, steep climbs, and virtual entry options with medals and shirts.

A 5k and 10k cross-country run at Albemarle CiderWorks on August 30, 2026, with virtual participation options. The course is new for 2025 and cider will be available after the event.

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

Experience a cross country race through Nottoway Park followed by a community picnic. This event features a three mile course and a kids fun run to celebrate the end of the summer season.

A road race at Fifty-Third Winery in Louisa, Virginia on September 5, 2026 offering 5K, 10K and several virtual options, with proceeds benefiting Hooves & Paws Animal Rescue.

A 71-mile, orange-blazed circuit on the Massanutten Trail with rugged, rocky terrain, multiple aid stations and two drop bag options, strict qualification and entry limits, and enforced cutoffs.