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Trail Running Calendar near Queen Anne 2026-2027

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Explore the top trail runs near Queen Anne for 2026-2027! We've gathered 7 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
A trail 25K in Queen Anne, MD on Nov 21, 2026 featuring mostly single-track terrain, three aid stations, and awards for the top three men and women.
A community 5K at Killens Pond State Park on November 28, 2026, supporting Milford High School Cross Country with chip timing, awards, and post-race refreshments.
December 2026
Eight hour trail endurance race at Terrapin Nature Park where each 2.8 mile lap fills a participant stocking with surprises and top finishers earn awards.
A 15K trail race at Quiet Waters Park in Annapolis on December 13, 2026, part of the Championship Series with special rates for Striders members and race day registration.
January 2027
Loop-format trail races at Killen's Pond State Park offering 50K, 24-hour and 100-mile options on a mostly dirt 3.1-mile loop with limited facilities and a self-supported format.
Gravel-trail 5K and 10K at Terrapin Nature Park on January 23, 2027, with chip timing, water views, series points, and a post-race drink at Cult Classic Brewing.
May 2027
A chip-timed 5K at Harvest Ridge Winery in Marydel DE with vineyards, a wooded trail, age group awards and a complimentary glass of wine for finishers over 21.
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