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Trail Running Calendar near Sarasota 2026-2027

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Explore the top trail runs near Sarasota for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Nov
21
Sa

RUN Manatee - Rye Preserve 5K Run/Walk

Road Race Trail Run 5 km
A community 5K at Rye Preserve in Parrish, FL with mixed terrain, a free kids Fun Run, organized warm ups and yoga, and a portion of fees donated to Foundation for Dreams.
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
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
Jan
17
Su

Fiorelli Wine Run 5K

Trail Run 5 km
Timed 5K run or walk at Fiorelli Winery in Bradenton with a race shirt, medal that doubles as a wine stopper, a wine pour, and online results.
Jan
23
Sa

Scrub Jay Races

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.
Jan
30
Sa

Coo-Wah-Chobee 50k

Trail Run 5 km 25 km 50 km
Trail races in Venice FL on January 30, 2027 offering 50k, 25k, 5k and a youth 5k on mixed single-track and dual-track trails at Carlton Preserve.
February 2027
Feb
6
Sa

Gopherdillo Trail Run

Trail Run 5 km 10 km
A 5K and 10K trail run at Lake Manatee State Park on February 6, 2027, featuring mixed natural terrain, chip timing, on-course wildlife, and post-race awards and finisher items.
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.
March 2027
Mar
13
Sa

The Mile - Sarasota

Backyard Ultra 50 mi
A 12 hour last runner standing race at Celery Fields in Sarasota with repeated 1 mile laps, an adjustable 17 minute cutoff, 150 spots and a $75 entry fee.
Mar
20
Sa

Rainbow Run 5K - Bradenton

Road Race Trail Run 5 km
A community color run at Tom Bennett Park in Bradenton on March 20, 2027, featuring a 5K and a kids run for ages 12 and under.
June 2027
Jun
12
Sa

GCP Flag Day 5K

Trail Run 3 mi
In person 5K at Robinson Preserve on June 12, 2027 with a virtual option; entry includes a shirt, snacks and age group awards.
September 2027
Sep
11
Sa

Bennett Park at Dark

Trail Run 2 mi 4 mi
Nighttime neon runs at Bennett Park in Bradenton with 2 mile and 4 mile cross-country courses, neon lights, DJ, vendor village, and a required headlamp.
October 2027
Oct
16
Sa

Trick or Trot 5K - Englewood

Trail Run 5 km
Annual Trick or Trot in Englewood, Florida features a 5K trail run and a 1 mile Zombie Walk on October 16, 2027, organized by Zoomers Southwest Florida Running and Triathlon Club.
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