Trail Running Calendar Florida 2026-2027

Independence Double is a two-day running event in Winter Park, FL on June 27 and 28, 2026, offering 5K, 10K, half marathon, marathon, and 50K distances with single-day and both-days registration options.

A 37 mile point to point road ultra from Port Mayaca to Stuart Beach in Canal Point, Florida with solo and relay options. The race highlights discharge from Lake Okeechobee into the St Lucie River and finishes on the beach.

InHouse Ultra is a last one standing treadmill competition for 33 athletes held inside Run Unlimited and Twenty One Run. Competitors run five miles every hour and must complete each set to stay in the race.

A multi-distance ultramarathon based at the Environmental Learning Center in Vero Beach, Florida, built around eight out and back arms. Distances range from a 5K to 100 mile and finishing all arms within 32 hours earns an Octopus Buckle.

A trail event in Naples, FL on 07/11/2026 with an eight hour time limit to complete as many two mile loops as desired. A fully stocked aid station will operate for the event and parking is on Sabal Palm Road.

A 30K night trail race in Green Swamp West Tract near Dade City, Florida on July 18, 2026, with varied Florida terrain, aid stations every 3 to 5 miles, a post-race potluck and finisher glass options.

Timed 3, 6, 9 and 12 hour events on July 18, 2026 at Cecil Field in Jacksonville, FL. The race uses a flat 1.25 mile paved loop through pine trees and includes a 4 person relay option for the 6 hour.

A multi-distance event at Blue Jacket Memorial Park offering in-person and virtual options, chip-timed 5K/10K/half distances, youth pricing, participant shirts and medals, free photos, and finish-line ice cream.

Multiple loop based races on ancient coastal sand dunes in Jupiter, Florida, from a 13.2 mile half to a 102 mile ultramarathon, with heat and sand making each distance a demanding endurance test.

A cross-country 5K at Vista View Park in Fort Lauderdale on July 28, with separate student (18 and under) and adult (19 and over) races and gender divisions; timed by Pure Gold Timing and held on rolling-hill park terrain.

Flat, shaded trail loop near the river and ocean in Palm Coast, FL. Timed 12 hour and 6 hour events with a fully stocked aid station and experienced race staff.

Summer Sizzler in Tampa on 08/01/2026 features timed 5K 10K and 15K races, untimed 1 mile and kids dash, and a virtual option. The event includes chip timing, shirts and medals, free photos and finish line treats.

A self-supported six hour Fat Ass event at Walsingham Park in Seminole, FL on August 1, 2026. Runners use an approximately 3 mile paved out and back loop and self-record laps on clipboards for official results.

Experience the Withlacoochee Forest after dark in this night trail race featuring 5, 10, and 20 mile distances. Navigate single track trails under the stars with glow stick markers and a post race picnic celebration.

A five hour out and back on Section 4 of the Pioneer Trail in Middleburg, FL with technical single track, switchbacks and creek overlooks. Limited to about 40 participants and cupless with basic aid at the halfway point.

An 8-hour timed ruck at Ross Prairie Trailhead in Dunnellon, FL, featuring repeated laps on a **6.5 mile** loop through pine forests, oak hammocks, dry prairie and sandy berm roads. Self-crewing and nearby campground facilities are availabl..

Wildcat Ultras is a loop based ultramarathon at the Escambia County Equestrian Center in Pensacola, FL on September 5, 2026. Distances include 100 mile, 100K, 50 mile, 50K and 15 mile with chip timing and crew access.

An ultramarathon along the Pinellas Trail covering just over 46 miles in an out and back format between St. Petersburg, Tarpon Springs and Dunedin. Registration closes Sep 2 and a Facebook group is listed for updates.

A two-day cross country festival at Apalachee Regional XC Park in Tallahassee with nighttime collegiate, high school, middle school, and open heats, multiple distances, and team amenities including a coaches’ box and reserved areas.

A 9/11 memorial stair climb at the Seminole Hard Rock Guitar Hotel in Hollywood, Florida on September 11, 2026. Three climb options for firefighters and civilians, raising funds for the Wounded Veterans Relief Fund and Firefighters Benevole..