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Trail Running Calendar near Bluemont 2026-2027

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Explore the top trail runs near Bluemont for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Run or walk 5K, 10K, or a half marathon on scenic routes at Third Winchester Battlefield in Winchester, VA on August 8, 2026.
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.
A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026 with virtual options and a Sippin Series tie to the Farm Brewery.
Challenging 5 km and 10 km routes at Dirt Farm Brewing in Bluemont on August 29, 2026 with rugged terrain and virtual entry options.
September 2026
Cross country at Morven Park with a high school invitational plus an open 5K, featuring food trucks, music and a spectator friendly course.
A 71 miles clockwise circuit of the orange-blazed Massanutten Trail with multiple aid stations, mandatory qualifications, and strict cutoffs on a rocky, high-ascent route.
The Final Countdown Tribute at Amani Brewing in Martinsburg WV uses a 1.33 mile loop where allowed lap time shortens each circuit, eliminating runners until one remains.
A campus 5K run/walk on September 19, 2026 in Middletown, VA, with online registration, set fees, age group awards, and proceeds supporting a scholarship and employee wellness initiatives.
SPEAR 50K is a 50 kilometer trail race on September 19, 2026 at Sherando Park in Stephens City, Virginia. It is part of the Sherando Park Endurance Athletic Runners summer trail series and lists details and registration on RunSignUp and Facebook.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
Trail and bike events at Sherando Park on September 26, 2026 offering a 4 mile trail race, a one mile untimed fun run, and a 5.3 mile mountain bike time trial. Proceeds benefit the I'm Just Me Movement.
Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.
October 2026
A trail 5K at Claude Moore Park in Sterling VA on October 3, 2026, offering in-person and virtual entries with medal and shirt options.
A community trail event on October 11, 2026 at Bretton Woods Recreation Center in Darnestown, MD offering a 5K trail run and a 1 mile walk. The event raises funds and awareness for addiction prevention, education, and support.
Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.
Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.
Trail 5 km and 10 km races plus several virtual entry options at Conway Robinson State Forest on October 25, 2026; walkers are welcome.
Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.
November 2026
A pre Thanksgiving run at Barrel Oak Winery in Delaplane offering 3K and 6K courses, virtual entry options, and walk and leashed pet access.
A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are requested.
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