Trail Running calendar near Upper Marlboro 2026-2027

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

The Sweet Air Trail Race features an adventurous 8-mile trail course in Gunpowder State Park. Runners will cross water and county lines on a route with rolling hills. Free registration is capped at 100 participants.

A cross country 5k and 10k at 868 Estate Vineyards with chip timing, a virtual option, race awards, and a postrace glass of wine for participants.

Tackle the flowy and fun trails at Schaeffer Farms in Germantown, Maryland. Choose from a 5K or a 10K++ course featuring single-track, stream crossings, and open fields. Enjoy post-race food, optional medals, and a festive atmosphere.

Run a festive half marathon or 5K on the scenic C&O Canal path in Georgetown. The event benefits the Purple Heart Foundation and counts towards year-long running series points. Participants receive a medal, tech shirt, and chip timing.

Run a technical 8K trail through vineyards and along the river at Bohemia Manor Farm. The chip timed event includes a tech shirt and wine glass. Celebrate after with a waterfront party featuring live music and food.

Explore the wooded trails of Little Bennett Regional Park in this trail run. Choose between a beginner-friendly 5K+ or a 10K course featuring single-track paths, hills, and streams. The event includes race swag, post-race food, and a free k..

The MD Heat Trail Race on August 15, 2026, offers 50K and 25K trails with river crossings and valley views. Finish with a celebration featuring craft beer and BBQ.

Run on the flat, scenic dirt trails of Leopold's Preserve in this 5k and 10k event. Participants receive a medal, shirt, and chip timing, with points counting towards several annual series. A virtual race option is also available.

The Inferno 10k is a forest trail race on a looping course behind Dirt Farm Brewing in Bluemont. Runners tackle a route with roots, rocks, and elevation changes. Finishers earn a medal, a tech shirt, and a post race beer.

A trail run in Seven Valleys, PA on September 12, 2026 offering 5K and 10K routes. Registration is expected around July 1, 2026 and a free volunteer registration option is available.

Run through a scenic 1000 acre farm bordering the Rappahannock River followed by live music and craft beer at Creekside Farm Brewery. Enjoy chip timed 5K or 8K trail courses with custom swag and local food trucks.

The Pemberton 24 is a unique 24-hour challenge in Maryland's Pemberton Park. Runners and teams attempt to complete as many hourly 5 km loops as possible, earning points for each one. It's a test of endurance with a supportive camp atmospher..

Trails 4 Tails offers a 40-mile ultra, a 40-mile team relay, and a 25K on a scenic multi-loop course through Codorus State Park. The trail route features varied terrain and changes direction each year. All races finish at a stocked pavilion..

Event Information The River's Edge Endurance Challenge takes place in Brunswick, Maryland. The event is the 8th annual edition and offers three different race distances. Distances 5K (3.1 miles) 3 Hour Endurance Race 6 Hour Endurance Chall..

Event Overview The Conestoga Trail Run is a 10-mile trail race in Holtwood, Pennsylvania. The event uses rocky and hilly trails with numerous small stream crossings. It is described as requiring experience and runners should be aware of pot..

This community 5K run/walk takes place on a wide natural trail at the Agricultural History Farm Park. The event includes a pre-race pep rally, post-race snacks, and awards for top finishers.

Run with your dog at the Howlin' Coyote Canicross Trail Race in King George, Virginia. Choose between a 10K or a 1 mile event on varied terrain. Your entry supports the Friends of Caledon State Park.

The Kettle Cooker Five & Dime is a trail race on the scenic and historic paths of Glenroy Preserve. Choose from four looped distances, all featuring hills, creek crossings, and ample aid station support. The event includes chip timing, a ra..

The Rick O'Donnell Memorial Ultra Challenge offers a 5-mile trail run plus timed 4-hour and 8-hour events. Held at Milkhouse Brewery in Mount Airy, MD, it supports a local running club's scholarship fund.