Trail Running calendar near Woodstock 2026-2027

In person 5K and 10K on July 25, 2026 at 868 Estate Vineyards in Purcellville with virtual entry options and varying registration periods.

Trail running at Button Farm in Germantown, MD over twisty single track with stream crossings, log ramps, and farm fields. Options include a 5K and an about 10K course with aid stations, post race food, and optional medals.

A 5K and half marathon run along the Chesapeake & Ohio Canal path in Georgetown Washington DC on July 25, 2026. Walkers are welcome and virtual entries are available with medal and shirt options.

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 community 5K trail run at Rock Creek Picnic Shelter A in Rockville, part of the PAMOJA Weekend celebrating unity, culture, and wellness. The event is hand timed and includes a participant T-shirt and finisher medal.

Run through the wooded singletrack trails and streams of Little Bennett Regional Park in Maryland. Enjoy a community atmosphere with professional timing, post race breakfast burritos, and distances for different experience levels.

A rugged multi-lap 29.0 mile event near Crozet, VA featuring about 7,610 ft of climb on a steep gravel road. Entry is limited to 65 runners, carries a small fee, and operates with a waitlist.

A relaxed practice run on August 2, 2026 at Fountainhead Regional Park with route options from 6 to 13+ miles. Entry is open but limited to 60 and requires sign up; light refreshments are provided.

A scenic Winchester VA event on August 8 2026 offering 5K, 10K, a half marathon and virtual entry options with medals and shirts available.

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..

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 relaxed practice run at Fountainhead Regional Park offering multiple distances up to 13.1 miles on August 2 and August 15, 2026. Entry is open but limited to 60 participants and runners are responsible for their own medical needs.

A 7K trail race at The Woodstock Equestrian Center in Dickerson, Maryland, presented as part of MCRRC's low key series for members. Non member registration has a $20 fee and runs from February 10, 2026 to August 16, 2026.

A Broad Run event on August 23, 2026 offering 5K and 10K distances plus multiple virtual options, noted as part of a Sippin Series with the local brewery.

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 event at Dirt Farm Brewing in Bluemont VA offering 5K and 10K courses over rugged terrain with virtual entry options on August 29, 2026.

A cross country 5 km and 10 km at Albemarle CiderWorks in North Garden, VA on August 30, 2026, offering in person and virtual entries plus post race cider.

A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.

A 3 mile cross country race through Nottoway Park in Vienna, VA on 08/30/2026 with a kids dash and a club picnic that includes food and drinks. Registration is free for members and $10 for nonmembers.