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Trail Running Calendar near Prince Frederick 2026-2027

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Explore the top trail runs near Prince Frederick for 2026-2027! We've gathered 5 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
19
Sa

Run the Vineyards - Running Hare 5K

Road Race Trail Run 5 km
A chip-timed 5K run/walk at Running Hare Vineyard on September 19, featuring a race shirt (if registered by Aug 31), a drink ticket, finisher medal, and awards by age group.
October 2026
Oct
11
Su

Run the Vineyards - Running Hare 5K

Road Race Trail Run 5 km
A scenic chip timed 5K at Running Hare Vineyard on October 11, 2026 with a complimentary drink for those 21 plus and post-race music and photos.
November 2026
Nov
7
Sa

Jug Bay Run/Walk for Wildlife

Road Race Trail Run 5 km 10 km
Support Patuxent River wildlife conservation by participating in a 10K, 5K, or 3K walk along a flat course through scenic river banks and wildlife sanctuaries.
Nov
14
Sa

Rosaryville Veterans Day Trail Race

Trail Run 20 km 50 km
Experience the natural beauty of Rosaryville State Park at this classic single track trail race featuring 50K and 20K distances through wooded meadows and rolling hills.
April 2027
Apr
10
Sa

Run the Vineyards - Ingleside Vineyards 8K

Trail Run 5 km 8 km
Runs through 50 acres of vineyards at Ingleside Vineyards with 5K and 8K chip timed courses, plus post race wine and live music.
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