Queen Anne
Trail Running Calendar near Queen Anne 2026-2027
Explore the top trail runs near Queen Anne for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
An evening 5K and 1 mile walk on a farm in Lincoln DE featuring horses, Latin music, cultural activities, food and vendors.
25K trail race in Queen Anne, MD on November 21, 2026 with three aid stations, trail food including churros, and awards for the top three men and women.
A community 5k run/walk and a separate competitive walking 5k at Killens Pond State Park on November 28, 2026. The event supports Milford High School Cross Country and features chip timing, awards, shirts, 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
Trail 5K and 10K at Terrapin Nature Park with gravel routes and Chesapeake Bay Bridge views, chip timing, medal and technical shirt, and a post race brewery drink.
May 2027
5K at Harvest Ridge Winery crossing MD and DE through vineyards, wooded trail and country road, with live music, a food truck and complimentary wine and keepsakes.