Trail Running calendar near Middletown 2026-2027

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.

A 5K and 10K run around the grounds of 868 Estate Vineyards in Purcellville, Virginia on July 25, 2026. Virtual entries and tiered registration options are offered, including choices for medals and shirts.

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.

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 in Derwood, MD, on July 26, 2026. Part of the PAMOJA Weekend, the event highlights unity, culture, wellness and community connection.

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 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 road and virtual event on August 8, 2026 at 251 First Woods Drive in Winchester, VA offering 5K, 10K, and half marathon distances with virtual options. Walkers are welcome and registration fees increase closer to the event.

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..

An annual event on August 9, 2026 in Schellsburg offering a 5K run and two 5K walks. The race raises funds for memorial scholarships and features age group awards, race shirts for preregistered entrants and professional timing.

A trail 5K in Gettysburg on August 15, 2026, with a race shirt option for early registrants and an event bottle opener medal. Brewfest options and tours of the Daniel Lady Farm House and Barn are available the same day.

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 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 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 trail run at Dirt Farm Brewing in Bluemont, VA on August 29, 2026, with on-site 5K and 10K courses over rugged, hilly terrain plus several virtual entry options and tiered registration fees.