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Trail Running Calendar near Derwood 2026-2027

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Explore the top trail runs near Derwood for 2026-2027! We've gathered 69 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

December 2026
Trail races at Fountainhead Regional Park on December 6, 2026 offer 4.8 mile and 10.5 mile courses with aid stations, porta-johns, race swag, and a supervised kids program.
Three races on the C&O Canal in Georgetown and Fletcher’s Boathouse: 5K, half marathon and a Boston qualifying full marathon with chip timing and medals.
A VHTRC holiday time 50k out and back on the Bull Run-Occoquan Trail from Hemlock Overlook to Fountainhead, with four aid stations and a GPX file for navigation. Entry includes lodge access, stocked aid stations, and a catered after party for $20.
A 13.1 mile out and back on the C&O Canal Towpath at Carderock Recreation Area with online registration, two water stops, live timing, and post-race refreshments.
A morning 5k and 10k at Burke Lake Park on December 24 with chip timing, finisher medal, technical shirt, a virtual option, and series points.
January 2027
January 17, 2027 race in Georgetown offering a half marathon and 5k on the C&O Canal path with chip timing, medals, shirts, and a virtual option
Chip timed 5K, 10K and half marathon on the C&O Canal towpath with minimal elevation, race series points, medals and technical shirts.
A 15.5 mile winter training run from Fountainhead along the blue blazed BROT to Bull Run Marina with minimal marking and limited water aid.
Trail races of 13.1, 6.55 and 3.1 miles on the Patuxent and Wincopin trails in Columbia, MD; registration includes shirt, medal and knit gloves.
February 2027
Looped trail event at Rockburn Branch Park offering a full 50k (six 5.179 mile loops), relay teams of two to six runners, or single loop options.
Scenic 5k, 10k and half marathon along the Potomac at Great Falls Park with chip timing, finisher medal, technical shirt and a virtual race option.
A 7-mile out-and-back lollipop loop at Fountainhead Regional Park with rolling hills, minimal markings, shared pot-luck aid, and the chance to run multiple laps.
Out-and-back 8k and 16k along the C&O Canal in Great Falls Maryland, chip timed with medals, technical shirts and a virtual participation option.
Trail races at Rockburn Branch Park in Elkridge, MD, with 5 mile, 10 mile, and a two person 10 mile relay; registration runs Oct 30 to Dec 4, 2026.
March 2027
An eight hour timed trail run on a 5.5 mile single track loop at Little Bennett Park in Clarksburg, MD on March 6, 2027.
A 15.5 mile training run on the Bull Run Occoquan Trail covering the northern section of the BRR 50 Miler with rolling terrain, a midway water table, and blue-blazed routing.
Trail 5k & 10k at Paradise Springs on March 6, 2027 with chip timing, a wine finisher reward, and a virtual option.
Trail marathon and 50K at Seneca Creek State Park on single track trails, with on-course choice to stop at the marathon or continue to 50K.
Out and back races at Point of Rocks offering 5K, 10K and half marathon distances with chip timing, finisher medal and a virtual option.
5k and 10k out-and-back races on the C&O canal path near Smoketown Brewery with chip timing, a finisher medal, event shirt, limited water stations, and a virtual option.
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