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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 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

Trail Running Calendar United States
October 2026
Oct
17
Sa

Trick or Trot 5K - Englewood

Trail Run 5 km
A Halloween themed trail event in Englewood offering a 5K run and 1 mile walk on mixed dirt and gravel trails, with shirts, medals, costume awards and scholarship fundraising.
Oct
24
Sa

The Ainger Creek Trailblazer 5K

Trail Run 5 km
Community 5K trail run in Englewood on October 24, 2026 benefiting Dollars for Mammograms and the Englewood YMCA, with a kids fun run, awards, and post-race activities.
November 2026
Nov
7
Sa

Buddy the Bull Stampede

Trail Run 5 km 20 km
An outdoor event in Arcadia FL on November 7 2026 featuring a 5K trail run, a 15K mountain bike race and a combined 20K Stampede Challenge supporting Eirene Ranch.
Nov
22
Su

The Legacy Trail Ultra

Trail Run 60 km
A free 60K ultramarathon on the Legacy Trail in Sarasota, Florida on November 22, 2026, run as an out and back course with limited aid stations.
Nov
28
Sa

Trail Hog Half Marathon

Trail Run 5 km 10 km 13 mi
Trail Hog in Venice FL on November 28, 2026 features a 13.1 miles, 10K, 5K and virtual run with race shirts, refreshments, music and age group awards.
December 2026
Dec
12
Sa

Sandy Claws Beach Run

Trail Run 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
Coo Wah Chobee in Venice FL on January 30 2027 offers a single loop 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
Trail races of 15K, 10K and 5K take place in Venice, FL, with a virtual option; race entry includes a shirt, post-race refreshments, and age group awards.
April 2027
Apr
24
Sa

Gator Wilderness Camp Trail Run

Trail Run 5 km 10 km 15 km
Trail races of 5k, 10k and 15k across 250 acres at Gator Wilderness Camp School in Punta Gorda, with a kids dash, a one-day virtual option, and proceeds supporting the school.
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