Trail Running calendar near Gainesville 2026-2027

Experience a scenic run through the landscape of Twisted Oak Farm Brewery in White Post. This event features 4k and 8k distances followed by a post race beverage at the brewery.

Experience a scenic cross country trail run through Wilderness Run Vineyards featuring a 5K and 1 Mile distance. Enjoy post race live music and refreshments at the winery to support St. Patrick School.

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

This 41-mile mountain trail race loops through the George Washington National Forest, featuring waterfalls, cliffs, and 8,000 feet of climbing. With a strict field limit and remote course, crews are not permitted. Top finishers earn cash pr..

Experience a scenic trail run through the forests and fields of Rosaryville State Park. Choose from several distances on fast and smooth terrain located just off the Capital Beltway in Maryland.

Experience a timed trail ultra at Little Bennett Regional Park with 5 and 9 hour individual or relay options. Runners navigate a 4.4 mile loop supported by a fully stocked aid station in Clarksburg.

Run along the paved B&A Trail in Maryland at this established event featuring a full and half marathon. Managed by the Annapolis Striders, it offers a well supported experience starting at Severna Park High School.

Choose your challenge at UltraTrax Massanutten with distances ranging from 7 to 28 miles. Hike or ruck through the scenic Shenandoah Valley on a rugged course featuring forested singletrack and panoramic ridgeline views.

Run 7 miles of scenic trails at Cromwell Valley Park. Enjoy rolling hills, single-track paths, and a fast downhill finish. Proceeds support the park and therapeutic programs for veterans.

Experience a fast and flat trail run along the Rappahannock River in Fredericksburg. This 5k course features a smooth lollipop style loop with minimal elevation gain and scenic views starting from the local quarry.

Experience a 50 mile trail run along the scenic Occoquan River in Virginia during the peak of spring. This historic event features forested paths and the largest bluebell stands on the East Coast.

Run a scenic 5k cross-country course at a Virginia vineyard. The event welcomes runners and walkers alike and offers virtual participation options. It takes place in Warrenton on April 4, 2026.

Run a memorable 14-mile point-to-point trail adventure from one Sheetz to another. This untimed event features themed aid stations with unique snacks, supports local charities, and provides useful swag like an insulated travel mug.

Experience a hilly and technical trail race through the scenic property in Bluemont Virginia. Choose between the 5k and 10k distances and enjoy a glass of beer after conquering the technical terrain.

Experience a unique trail run on the private ThorpeWood estate in Maryland. Offering 5K and 10K distances, this club event features marked loops through beautiful natural terrain for FSRC members.

Experience a fast and flat race along the scenic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners are invited to set new personal records at Carderock Park.

Run to Remember is a multi-distance trail event held in Sykesville's Piney Run Park. Runners traverse a scenic 5.25-mile loop past woods, meadows, and a lake. The event honors lost loved ones and supports cancer research.

Join the Sip & Stride 5k and 10k in Louisa Virginia for a chance to earn points in the Sippin’ Series. Choose between in person racing or multiple virtual participation options with medals and shirts.

Enjoy a cross country style 5k run or walk through the scenic Hauser Hill Event Center. Participants receive a finisher medal and a pour of wine in a collectible glass at the finish line.

Run Fest at Panorama Farms offers a day of trail racing and community celebration on April 18, 2026. Choose from a 4-mile trail race, a team relay, or a 1-mile fun run, followed by a festival with live music and local food. It's a chance to..