Trail Running calendar near Live Oak 2026-2027

A timed loop event at Cecil Field in Jacksonville with 3, 6, 9, and 12 hour formats, a flat 1.25 mile paved loop shaded by pine trees, food and a main aid station, and a 4 person relay option for the 6 hour race.

A five hour Fat A$$ event on Section 4 of the Pioneer Trail in Middleburg Florida where participants run an out and back loop of about 2.5 miles as many times as possible. Limited field and cupless format with minimal aid provided.

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.

S.O.S. in Middleburg, FL uses a 2.75 mile Sandridge Trail loop with a 9K plus 3, 6 and 12 hour timeframes and ruck options. It is a cupless event with aid stations, hot food, awards, and proceeds benefiting local recovery nonprofits.

A community fund-raising run and walk in downtown Jacksonville offering 5K, 10K, and a one-mile option on September 26, 2026, with tiered registration fees and participant fundraising features.

An urban 5K adventure race in Tallahassee with at least five on course challenges and finisher medals. A separate untimed fun run under one mile is offered and T shirts are available for an extra $10.

Trail race at San Felasco Hammock Preserve near Alachua offering 25K and 50K loops on single track and double track trails with fields and hills. Net proceeds support Friends of San Felasco and finishers receive a custom medal and glass.

Run a USATF certified 5K cross country course through the historic grounds of Pebble Hill Plantation. This hilly race features varied terrain and supports the preservation of the museum house and estate.

Trail running event in White Springs, Florida offering 50K, 25k and 10k distances with aid stations and cutoffs. Races finish at Stephen Foster Folk Culture Center State Park and benefit the Florida Trail Association.

A backyard ultra at San Felasco Hammock Preserve State Park where runners repeat a 4.167-mile loop every hour until one completes a loop no other does. No on-course aid, limited base camp space, and basic facilities at the start/finish.

A multi-distance trail event in Middleburg FL on a scenic 7.2 mile loop offering 100 mile 50 mile 35 mile 14 mile and 7 mile options. The cupless race features staffed aid stations and a custom buckle for 100 mile finishers.

Trail races on the Pioneer Trail in Jennings State Forest near Middleburg FL, featuring 50K, marathon, 12K and a 7K closer to five miles. Courses use diverse single track with technical sections, aid stations about every 2.5 to 3 miles, and..

Sombrero Ultra Running Festival in Middleburg, Florida is a multi day ultrarunning weekend with timed events from three hours up to 48 hours plus 48 hour team relays. The festival includes a runner village, a single aid station, on site med..

Trail races at Manatee Springs State Park on February 19 and 20, 2027 include 5K, 10K and a half marathon on smooth, shaded trails. Weekend bundle options include a special finisher item and race swag.

The Angry Tortoise 50K will take place in Bryceville on Saturday 20 February 2027. You can run between 25 and 50 kilometers.

Obstacle course and trail races at Diamond D Ranch near downtown Jacksonville, featuring Sprint, Super, trail, and kids distances. The course runs through ranch terrain with mud and natural obstacles and offers spectator and volunteer optio..

A Spartan Trail stop at Diamond D Ranch near Jacksonville with a mostly flat but occasionally technical, muddy course; options include a 10K and a half marathon and the weekend also features Spartan obstacle races.

UltraTrax Suwannee in Live Oak Florida on March 13, 2027 offers one to four 7 mile loops through oak and pine forests, with optional 10, 20, or 35 lb rucking and official finish rewards.

An off-road 5K at Seamark Ranch with 26 obstacles across woods, fields, ponds and mud, plus a 1 mile fun run. The event is a fundraiser for Seamark Ranch and operates rain or shine.

A family obstacle race at Phipps Farm in Tallahassee featuring junior, youth and 5K courses plus food trucks and festival activities. Registration windows, age rules, and participant limits are set by the organizer.