Englewood
Trail Running Calendar near Englewood 2026-2027
Explore the top trail runs near Englewood for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail 5K and 1 mile walk at Ann and Chuck Dever Regional Park with costume awards, finisher medals, post race refreshments, and proceeds to a local scholarship fund.
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
A multi-discipline trail event in Arcadia FL with a 5K run, 15K mountain bike race, a combined Stampede Challenge, and post-race food and family activities.
A free 60K out-and-back ultramarathon on the Legacy Trail in Sarasota, FL, with limited aid stations and a 10 hour cutoff on November 22, 2026.
December 2026
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
Family and pet friendly trail 5K at Gator in the Rough in Bokeelia with participant medals, guaranteed tech shirts for early registrants, and proceeds supporting the Kiwanis Club.
February 2027
March 2027
A 12 hour trail endurance event at Celery Fields where runners repeat one mile laps with a 17 minute cutoff in a last runner standing format.
April 2027
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.