Trail Running calendar near Anne Arundel County 2026-2027

Experience an iconic spring ultra marathon featuring a fifty kilometer double loop through Susquehanna State Park. Navigate single track trails and stream crossings with over four thousand feet of climbing.

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.

Join The Husky Run 5K on the scenic Ma and Pa Trail in Bel Air. This walk and run event is open to all ages and abilities. Every finisher earns a limited-edition Husky medal.

Experience a unique trail run through the grounds of Genesis Church featuring a fun foam finish. Support healthcare services for the uninsured while enjoying distance options for runners, walkers, and children in York.

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.

The Montchanin Trails 5K is a trail run on March 29, 2026, at Longwood at Granogue in Wilmington, DE. The 5K course features single-track trails, hills, and varied terrain. Registration is limited to 300 participants and includes a t-shirt..

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.

The Trail Demon 10k is a technical trail race on a forest loop at Dirt Farm Brewing in Virginia. Runners receive a finisher medal, a tech shirt, and a post race beer. Proceeds support the Boulder Crest Foundation for veterans and first resp..

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.

A turtle-themed 5K trail run at Hopkins Farm Brewery that supports local wildlife conservation. Participants receive a wooden medal and costume prizes are awarded. The event concludes with a festive after-party featuring live music.

Run a fast and flat course along the C&O Canal Towpath in Maryland's Carderock Recreation Area. Choose from a 5K, 10K, or Half Marathon distance, with walkers welcome. The event also offers a virtual participation option.

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.

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.