Trail Running Calendar Maryland 2026-2027

We have found 57 Trailruns in Maryland. Check below where and when you can find the races.

A chip timed 5k at Corteau Vineyards in Mechanicsville, Maryland on June 13, 2026, featuring vineyard scenery, a t-shirt, collapsible wine glass, finisher medal that doubles as a wine stopper, and an on-site wine pour.

A self-timed 4 miles run in Bel Air as part of the Harford County Running Club Dog Days of Summer Series. The course mixes trail and road, is not stroller friendly, and parking is at Prospect Mill Park.

A Juneteenth trail event in Germantown on June 19, 2026 offering 6K and 12K distances plus virtual options, with a hilly course around Button Farm and the Schaeffer Farm Trails and welcome to walkers.

A summer cross-country series with four races, three confirmed at local high schools. Online pre-registration is free and a $5 cash fee is collected on race day.

A rugged out-and-back trail event in Cunningham Falls and Gambrill State Parks on June 20, 2026 offering a 50K and a 25K Half Cat with three aid stations, strict crew and hydration rules, and a recently rerouted section that lengthens the c..

A free night training run in Salisbury, MD offering six hours of repeated 5K loops on marked trails. Space is limited to 50 runners and participants must provide their own hydration and fuel.

Trail races at Seneca Creek State Park on June 27 2026 feature 5K and 10K courses through lakeside singletrack and streams, with aid stations, park parking, post race food, and age category awards.

A 5K trail race at Agricultural History Farm Park in Derwood, Maryland. MCRRC members run free with a 2026 bib and chip while non members pay a set fee and can register online through race start.

July 2026

A themed Forrest Gump fun run at Lakeside Loop in New Town Village, Owings Mills, offering a full 4.4-mile loop or a 1-mile out-and-back option. The event is free and participants are encouraged to wear the red hat, yellow top and red short..

A trail-based running event at Needwood Lake Circle in Maryland on July 11, 2026 offering 5 km, 10 km and virtual entries with medal and shirt options.

A trail race at Gunpowder State Park listed as 7 miles with a route that crosses county lines, features rolling hills, water crossings and occasional mud. Registration is free and donations are accepted on race day.

A 6 hour endurance run at Quiet Waters Park in Annapolis with solo and three person relay options, run on a roughly 4.25 mile shaded loop. The event donates a portion of fees to the Semper Fi Fund.

Trail running at Button Farm in Germantown, MD over twisty single track with stream crossings, log ramps, and farm fields. Options include a 5K and an about 10K course with aid stations, post race food, and optional medals.

August 2026

Trail races at Bohemia Manor Farm Winery featuring *5K* and *8K* courses through vineyards, riverfront and wooded trails, chip timing with live results, finisher wine glass and an on-site after party with music and food.

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.

An 8K cross-country race at Anne Arundel Community College on August 2, 2026, part of the Annapolis Striders Championship and Maryland/DC RRCA Grand Prix Series, with pre-registration fees and race day registration available.

Trail races on mostly single-track woods in Gunpowder Falls State Park, using a roughly 4 mile loop. Participants can run one loop for 4 miles or repeat it for 8 miles; registration is race morning only.

Part of the Harford County Running Club Dog Days of Summer Series, Rigbie Farm 5k is a free, self timed grass and trail loop near Darlington, MD. Parking is at Rigbie Farm and non members may take part in three free runs.

A trail race in the Patapsco Pickall Area near Elkridge, MD offering 25K and 50K courses with single-track, river crossings and 2000+ ft of climbing, staffed aid stations, and a post-race food and beer spread.

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.

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