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Trail Running Calendar near Englewood 2026-2027

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Explore the top trail runs near Englewood 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.

October 2026
Oct
17
Sa

Trick or Trot 5K - Englewood

Trail Run Walk 5 km
A Halloween themed trail event in Englewood on October 17, 2026 featuring a 5K run and a 1 mile walk, costume awards, finisher medals, post-race refreshments, and proceeds supporting the Zoomers Scholarship Fund.
November 2026
Nov
7
Sa

Buddy the Bull Stampede

Trail Run 5 km 20 km
Buddy the Bull Stampede in Arcadia FL on 11/07/2026 features a 5K trail run, a 15K mountain bike race and a combined Stampede Challenge, with post-race food, finisher hats, activities for families, and support for Eirene Ranch.
Nov
28
Sa

Trail Hog Half Marathon

Trail Run 5 km 10 km 13 mi
Experience the natural beauty of Carlton Reserve at this Florida trail event. Runners can choose between three distances and enjoy a pre race stretch session with recovery snacks and awards for various age groups.
December 2026
Dec
12
Sa

Sandy Claws Beach Run

Trail Run Walk 5 km
The 50th Annual Sandy Claws Beach Run at Siesta Beach features a chip-timed 5K, a 1-mile fun run and a virtual 5K, with finisher medals, age-group awards, music, food and a holiday costume contest.
January 2027
Jan
23
Sa

Scrub Jay Races

Trail Run 5 km 10 km
Trail and road races at Oscar Scherer State Park include a 5K and a technical 10K plus virtual 5K and 10K options. Registration includes a finisher medal and a race shirt while supplies last.
Jan
30
Sa

Coo-Wah-Chobee 50k

Trail Run 5 km 25 km 50 km
Trail race at Carlton Preserve near Venice FL offering 50k, 25k, 5k and a youth 5k on mixed single and dual track trails.
February 2027
Feb
21
Su

Sasquatch - Venice

Trail Run 5 km 10 km 15 km
Experience a scenic trail race through the Carlton Reserve in Venice with distances ranging from 5k to 15k. Enjoy post race snacks and unique handmade wood awards in a festive community atmosphere.
April 2027
Apr
24
Sa

Gator Wilderness Camp Trail Run

Trail Run Walk 5 km 10 km 15 km
Trail races on the wooded 250 acre grounds of Gator Wilderness Camp School include 5K, 10K and 15K options, a kids dash, and a one day virtual race. Proceeds benefit the school and shirts are guaranteed for early registrants.
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