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Trail Running Calendar near Milton 2026-2027

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Explore the top trail runs near Milton for 2026-2027! We've gathered 6 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Oct
10
Sa

Century Lions Club Cross Country 5K

Trail Run 5 km
A community cross country 5K at Anthony Pleasant Park on October 10, 2026 with age-group medals and awards presented by the Century Lions Club.
November 2026
Nov
14
Sa

Krul Lake Half Marathon

Trail Run 13 mi
Experience a scenic trail run through the long leaf pines of Blackwater River State Forest. Enjoy a post race BBQ and the opportunity to swim in Krul Lake after completing the half marathon course.
February 2027
Feb
13-14
Sa - Su

Death by 5k Coldwater Creek

Backyard Ultra 5 km 50 km
Test your endurance at Coldwater Creek by completing ten 5k runs over 24 hours. Navigate single track trails and sandy roads while enjoying provided hot meals and on site camping at this unique ultra distance challenge.
Feb
13
Sa

Blackwater Heritage Trailblazer

Trail Run 3 mi 13 km
A community running and walking event on the paved Blackwater Heritage Trail in Milton, FL, offering a 13K race with awards, a 2.7 mile fun run/walk with prizes, para divisions, and a shirt purchase option.
Feb
27
Sa

Punch out Ultra

Backyard Ultra
Test your endurance at a private deer ranch in Molino with 8 hours to complete as many 4.2 mile laps as possible individually or as a team.
September 2027
Sep
4
Sa

Wildcat Ultras

Trail Run 15 mi 50 km ... 100 km 100 mi
Looped ultramarathon in Pensacola with distances from 15 miles to 100 miles on a runnable 2.5 mile grass and dirt course, USATF sanctioned and limited to 250 runners.
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