Trail Running calendar near Sykesville 2026-2027

An evening ruck march on September 25, 2026 at Gov. Dick with 8 mile, 4 mile, and junior divisions; weighted rucks are required for prize eligibility and proceeds support The Knights of the Kingdom and Gov. Dick.

An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.

Trail and bike events at Sherando Park on September 26, 2026 offering a 4 mile trail race, a one mile untimed fun run, and a 5.3 mile mountain bike time trial. Proceeds benefit the I'm Just Me Movement.

Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.

A 5K on the Ma & Pa Trail in Baltimore on September 26, 2026 with in-person and virtual options supporting Cancer Warriors Inc.

A *3 mile* Reunion Run at Hereford High School as part of the Bull Run Cross Country invitational. The race is open to all ages and carries a $10 registration fee, with registration listed from August 24 to September 26.

A community 5K and 1 mile kids run in West Grove PA on September 26 2026 supporting Avon Grove High School cross country with a three-loop grass course and race-day refreshments.

Experience a supported long distance run on the hardpacked dirt and gravel of the Torrey C. Brown Trail. This twenty mile event serves as an ideal training opportunity for those preparing for a fall marathon.

In-person 5K and half marathon on the Chesapeake & Ohio Canal in Georgetown on September 27, 2026, with virtual options and walkers welcome.

A 10 miles trail race in Holtwood, PA, over rocky, hilly trails with stream crossings and scenic overlooks. Chip timed, with aid stations, a strict 2.5 hour cutoff to mile 7, and one way bus transport to the campground start.

An annual community 5K run and walk at Agricultural History Farm Park in Derwood, Maryland on September 27, 2026, organized by MD District 15 Democratic Caucus. Offers adult and youth entries plus a free youth option with an accompanying ad..

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.

A community event at Cornwall Elementary with a 5K and a 1 mile fun run on the Lebanon County Rail Trail. The non-timed event includes a free family festival after the runs with food and an outdoor movie, with proceeds to the school PTO.

Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.

A parkside series of races at Burke Lake Park on October 3, 2026 offering 5K, 10K, half marathon and virtual options, with walkers welcome.

A community charity race in Gaithersburg on October 3, 2026, featuring cross-country 10K and 5K, a paved 1-mile accessible fun run, and a kids Trike-A-Thon. Proceeds support Comfort Cases and Covenant Life School and include a post-race bac..

Trail event at Prince William Forest Park with a 6.5 mile figure eight loop, a 30 km option, two aid stations, and an awards ceremony with a post race meal.

A trail 5K at Claude Moore Park in Sterling, VA on October 3, 2026, with in-person and virtual entry options and published registration fees.

A community trail festival in Shippensburg offering a half marathon, 5k, hike, 25 mile bike ride and a free 1 mile fun run for kids, with proceeds supporting the Cumberland Valley Rails to Trails Council.

Join this annual community trail run through the wooded trail network of Potomac Shores. Residents and guests can choose between 5K and 10K courses for a free morning of outdoor activity in Dumfries.