Trail Running calendar near Winchester 2026-2027

Scenic Georgetown races on the Chesapeake and Ohio Canal path with 5K, 10K, and a half marathon on July 26, 2026 plus virtual options.

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.

The Summer Burke Lake 5K & 10K will take place in Fairfax Station on Saturday 1 August 2026. You can run between 5 and 10 kilometers.

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.

Trail races of 5K and 3K at Codorus State Park Marina organized by Delone Catholic High School's cross country team; early registration includes a T-shirt and goodie bag and proceeds support several local funds.

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.

Participate in a 5K run or walk at the Somerset Historical Center to support the North Star Cross Country team. Enjoy a dedicated cross country course with awards for various age groups and included event t-shirts.

A low key trail run in Jefferson National Forest on a roughly 60 km loop with three aid stations and a shorter 50 km Party Route option.

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.

Trail event in Elkridge, MD with 25K and 50K options on rolling single track featuring technical sections, river crossings, multiple aid stations with real food, and a post-race pavilion gathering.

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 5K and 10K at Bull Run Marina on August 15, 2026 with on-site and virtual entry options including medal and shirt choices.

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.

Scenic 5K and Half Marathon along the Chesapeake & Ohio Canal in Georgetown with in-person and virtual entry options.

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 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, featuring in-person and virtual options and a new Sippin Series partnership with 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 event at Dirt Farm Brewing in Bluemont VA offering 5K and 10K courses over rugged terrain with virtual entry options on August 29, 2026.