Trail Running calendar near Middletown 2026-2027

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 on July 25, 2026 at 868 Estate Vineyards in Purcellville, Virginia offering 5 km and 10 km courses plus virtual entry options with varying fee tiers and medal or shirt choices.

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.

Christmas in July 5k & Half in Georgetown, Washington DC on July 25, 2026 features races along the Chesapeake and Ohio Canal path with 5K, half marathon and virtual options; walkers are welcome.

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.

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 out and back run near Crozet, Virginia covering about 29 miles with roughly 7,610 feet of climbing over five steep gravel laps. Limited to 65 runners, informal entry 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..

Races at Third Winchester Battlefield in Winchester VA on August 8, 2026 include 5K, 10K, a half marathon and virtual options with medal or shirt. Walkers are welcome and registration shows tiered pricing.

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 5K run plus two 5K walks on August 9 2026 at Camp Living Water in Schellsburg PA, raising funds for annual scholarships for Bedford High School students and for families facing financial need after the loss of a young person.

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.

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 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 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 trail-style 5K and 10K at Dirt Farm Brewing in Bluemont on August 29, 2026, with rugged terrain, steep sections, and winding paths; virtual entries available with different medal and shirt options.

A trail festival at Furnace Run Park with a 5K loop on mixed surfaces and a planned longer trail. Chip timing, awards by gun time, and proceeds benefit Friends of Shippensburg Community Parks.

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.

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.