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Trail Running Calendar near Osprey 2026-2027

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Explore the top trail runs near Osprey for 2026-2027! We've gathered 11 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 trails, a free family fun run in multiple distances, yoga, vendors, and charity support.
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
A timed 5K at Fiorelli Winery & Vineyard in Bradenton featuring chip timing, a finisher medal that doubles as a wine stopper, and wine pours included with registration.
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
Single loop trail races of 50k, 25k, 5k and a youth 5k at Carlton Preserve in Venice, FL on January 30, 2027, organized by RunFluent.
February 2027
Feb
6
Sa

Gopherdillo Trail Run

Trail Run 5 km 10 km
A trail event at Lake Manatee State Park on February 6, 2027 with 5K and 10K courses through dirt paths, sand and pine corridors. The race features chip timing, finisher medals, post race snacks and age group awards.
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 last runner standing 12 hour endurance run at Celery Fields in Sarasota featuring repeated one mile laps with a 17 minute cutoff and a 150 person field.
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.
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