Englewood

Trail Running Calendar near Englewood 2026-2027

Explore the top trail runs near Englewood for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026

The Legacy Trail Ultra

Sarasota | 28 mi from Englewood

Trail Run 60 km

Free 60K out and back ultramarathon on the Legacy Trail in Sarasota, FL, organized by the Manasota Track Club with a 10-hour cutoff and limited aid stations.

Free 60K out and back ultramarathon on the Legacy Trail in Sarasota, FL, organized by the Manasota Track Club with a 10-hour cutoff and limited aid stations.

Trail Hog Half Marathon

Venice | 11 mi from Englewood

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.

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

Sandy Claws Beach Run

Sarasota | 28 mi from Englewood

Trail Run 5 km

Siesta Beach hosts a chip-timed 5K, a 1-mile fun run and a virtual 5K with medals, awards, music and a holiday costume contest.

Siesta Beach hosts a chip-timed 5K, a 1-mile fun run and a virtual 5K with medals, awards, music and a holiday costume contest.

January 2027

Scrub Jay Races

Osprey | 18 mi from Englewood

Trail Run 5 km 10 km

Trail and virtual races at Oscar Scherer State Park on January 23, 2027, featuring a 5K, a technical Scramble 10K, finisher medals and post-race refreshments.

Trail and virtual races at Oscar Scherer State Park on January 23, 2027, featuring a 5K, a technical Scramble 10K, finisher medals and post-race refreshments.

Coo-Wah-Chobee 50k

Venice | 11 mi from Englewood

Trail Run 5 km 25 km 50 km

Trail event in Venice FL offering 50k, 25k, 5k and youth 5k on mixed single and dual track trails, organized by RunFluent.

Trail event in Venice FL offering 50k, 25k, 5k and youth 5k on mixed single and dual track trails, organized by RunFluent.

Pine Island Calusa Trail 5K Run

Bokeelia | 21 mi from Englewood

Trail Run 5 km

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.

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

Sasquatch - Venice

Venice | 11 mi from Englewood

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.

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.

March 2027

The Mile - Sarasota

Fruitville | 26 mi from Englewood

Backyard Ultra 50 mi

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.

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

Gator Wilderness Camp Trail Run

Punta Gorda | 19 mi from Englewood

Trail Run 5 km 10 km 15 km

Trail races at Gator Wilderness Camp School in Punta Gorda on April 24, 2027, featuring 5k, 10k, 15k, a kids dash and a one-day virtual event.

Trail races at Gator Wilderness Camp School in Punta Gorda on April 24, 2027, featuring 5k, 10k, 15k, a kids dash and a one-day virtual event.