Trail Running Calendar Florida 2026-2027

The Grayt Jackalope 10 and 5 miler features two trail courses starting and finishing at Grayton Beach State Park, with awards for top finishers and age group winners and packet pick up the day before at Fleet Feet Inlet Beach.

Trail Florida is a December team trail relay at Alafia River State Park near Tampa featuring a 126.4-mile course, multiple team formats, on-site camping in Ragnar Village, and weekend activities including a bonfire, music, glamping, and hol..

Multi-distance trail event in Middleburg, FL on Dec 5 to 6, 2026 featuring a scenic 7.2 mile loop, cupless aid stations with hot food, campground campsites, published cutoffs for each distance, and a buckle for 100 mile finishers.

A marked 16.8 mile course preview for the 2027 LH100 at Colt Creek State Park in Lakeland, FL with limited unstaffed water stations, primitive camping available, and a park entry fee.

The Congaree and Penn Spiked Apple 5k will take place in Duval County on Saturday 5 December 2026. You can run 5 kilometers.

Caloosa Fest in Alva, Florida offers a Half Marathon and a 5K held on the Caloosahatchee Regional Park mountain bike trails, featuring single track, grass sections, aid stations, packet pickup options, and on-site vendors.

The 50th Sandy Claws Beach Run at Siesta Beach offers a chip-timed 5K, a 1-mile fun run and a virtual 5K, with finisher medals, age-group awards, music and a holiday costume contest.

A coastal ultramarathon on 12/12/2026 in Pensacola tracing the Gulf shore between Big Lagoon State Park and Fort Morgan. Options include 50 Mile and 50K distances with solo and relay formats.

A trail running event in Lutz, FL on December 12, 2026 with multiple formats including a new 13.1 mile option and a 2-person relay. The course is a 4.45 mile loop of singletrack, doubletrack and grass, and finishers receive a woodal.

Candy Cane Course in Orlando on 12/13/2026 offers 5K, 10K, 15K, a 1 Mile, a Kids Dash and a virtual option. Entries normally include a designer shirt, custom bib and finisher medal, with youth pricing for ages 12 and under.

A two day obstacle course weekend at Skipper Ranch in Sebring Florida on Dec 19-20 2026 offering Sprint 5 km, Super 10 km, Beast 21 km, a kids race, an obstacle workshop and spectator options.

A holiday run in downtown Dunedin on December 19, 2026 featuring 5K 10K and 15K routes on the Pinellas Trail with electronic timing finisher medals shirts and a post race beer option for those 21 and over.

A multi-format event at Lake Wailes Park on December 19, 2026, offering a 4.17 mile loop, 6 hour and 12 hour timed races, and a 12 hour relay for teams up to five, with aid stations, awards, participant shirts, and food at the Runners Villa..

An invitation-only, no-fee 100-mile loop race in Titusville on December 19–20, 2026, run as 29 laps of a 3.46-mile trail loop with varied surfaces and a 32-hour time limit; entries are drawn from a June wait list and the field is capped at..

A looped trail event in Jupiter Ridge Natural Area offering a 50K, a half marathon, and a 30K night race across ancient coastal dunes. Entries are limited to protect the scrub habitat and aid stations are placed so runners are never more th..

A 36.8 mile loop around Choctawhatchee Bay on December 27, 2026, offered as an ultra or as relays for two to six runners. The course passes through Destin, Bluewater Bay, Niceville, Valparaiso, Shalimar and Fort Walton Beach.

Holiday-themed races at Gadsden Park in Tampa on December 27, 2026, with distances from a kids 50 m dash to 15K, plus a virtual option, chip-timing, shirts, medals, photos, and finish-line treats.

A 125 miles out and back ultramarathon on Florida's Ocean to Lake Hiking Trail between Hobe Sound Beach and Lake Okeechobee. No aid stations or crew support; runners use four volunteer managed supply buckets and have 48 hours to finish.

An 18 hour fixed-time urban ultra on January 9, 2027 where runners choose their own route through Miami landmarks. Rankings use GPS-verified miles and selfies at each landmark, with podiums for those who visit all required points and return..

A beach race in Daytona Beach on January 9, 2027 offering 5K and 10K courses on hard-packed sand, chip timing, participant shirts, finisher medals, and a combined 15K Bandshell Challenge for both races.