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Trail Running Calendar near Okaloosa Island 2026-2027

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Explore the top trail runs near Okaloosa Island for 2026-2027! We've gathered 4 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

December 2026
Dec
27
Su

Round The Bay Relay and Ultra

Trail Run 5 km 37 mi
A 36.8 mile relay and ultra around Choctawhatchee Bay near Destin, Florida, divided into six legs with staggered starts and a separate 5K recovery run.
January 2027
Jan
23
Sa

Ellie Biscuit 20 & 10-Mile Trail Trot

Trail Run 10 mi 20 mi
A trail race on January 23, 2027 at Pt. Washington State Forest offering a 10-mile loop or a 20-mile double lap, official race hoodie, course maps, and age-group awards.
February 2027
Feb
20
Sa

In the Woods 50K

Trail Run 50 km
Trail 50K at Point Washington State Forest with three laps or team relays, long sleeve tech shirt and finisher medal; solo runners under 4 hours earn the U4 Club award.
April 2027
Apr
3
Sa

The Savage Loop

Trail Run 10 mi 19 mi ... 35 mi 42 mi
A 42 mile ultramarathon around Choctawatchee Bay in Niceville, FL with 10, 19, 26.2 and 35 mile options and proceeds benefiting Workshop of Wishes.
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