Trail Running Calendar Florida 2025-2026

The Masaryk Wine Run 5k will take place in Masaryktown on Sunday 25 January 2026. You can run 5 kilometers.

This ain't your Mothers 50k & Trail Marathon is an annual trail running event held in Middleburg, Florida, within the scenic Jennings State Forest near Jacksonville. The race features multiple distances including a 50K, trail marathon, 12K,..

Event overview The Pine Island Calusa Trail 5K Run and Walk takes place on Saturday, January 31, 2026, in Bokeelia, FL. The event is a family- and pet-friendly walk/run partnered with the Florida Museum's Randell Research Center. The course..

Event overview The Coo-Wah-Chobee takes place on January 31, 2026, at Carlton Preserve in Venice, FL. The organizer is RunFluent. This is the second annual running of the event and it uses a single loop course through Carlton Preserve. Race..

Forgotten Florida is a trail race weekend in Christmas, Florida on Jan 31 Feb 1, 2026, featuring 100, 50, 15 and 8 mile options across palm groves and pine flatwoods. Expect single track, abundant wildlife, and classic low country trail sce..

Event details The Mardi Gras Canicross, 10k and 5k Run takes place on Sunday, February 1, 2026, at Celery Feilds in Sarasota, Florida. The event location is listed as 900 Center Rd, Sarasota, FL 34240. The event program includes the followi..

Event overview The AdventHealth Nighthawk Trail Run takes place at Colt Creek State Park in Lakeland, Florida on Saturday, February 7, 2026. The event offers three options: Night Owl 5K (3.1 miles) Coyote 10K (6.2 miles) Nighthawk 15K Chal..

The Wagging Tails on the Trails is an annual running event held at Pepper Park Riverside on Hutchinson Island in Fort Pierce, Florida. Scheduled for February 7, 2026, it features a 5K trail run/walk and a new 9K trail run option supporting..

Gopherdillo Trail Run The Gopherdillo Trail Run takes place on Saturday, February 7, 2026, at Lake Manatee State Park in Bradenton, FL (20007 FL-64, Bradenton, FL 34212). The event includes two distances: 5K 10K Course and logistics Both..

Death at DuPuis is a backyard style ultrarun in scenic DuPuis where runners repeat a four mile loop each hour until only one keeps going. The community event awards a Bronze Ticket, $1,000, and raises funds for local trail conservation.

Event overview The Sombrero Ultra Running Festival (SURF) is the second annual multi-day running festival held at the Clay County Regional Sports Complex, 4790 Victory Lane, Middleburg, FL. The event date is February 13, 2026. Registration..

Event overview Death by 5k Coldwater Creek is a multi-stage running challenge held at Adventures Unlimited Outdoor Center in Milton, Florida. The event requires participants to complete ten 5k races spread across a 24-hour period, with each..

Whispering Pines Trail Event : Inverness, FL (Feb 14, 2026) This is a day-long trail event held at Whispering Pines City Park in Inverness, Florida. The event is free; donations are used to cover park rental, insurance, aid station supplies..

Event overview Skunk Ape’s Revenge takes place on February 14, 2026 at the Green Swamp - West Tract near 13347 Ranch Road, Dade City, FL 33525. The event offers the following distances: 60K 30K 30K Ruck Awards are given to the top four me..

Explore scenic Lake Apopka trails with 30K, 8 Mile, 5K and a virtual trail option. Get a technical shirt, finisher medal and post race food while supporting Friends of the Green Mountain Scenic Byway.

The Sasquatch Run in Venice, Florida, is a vibrant trail running event held at Carlton Reserve. It offers multiple race distances including 15k, 10k, 5k, and a virtual race option, catering to a wide range of runners. Participants enjoy a f..

Event overview The Painted Horse Urban Ultra takes place on February 21, 2026, in Ocala, FL, with a listed location at 1 SE Broadway St. The event is presented as a self-supported urban adventure run rather than a timed race. The route is a..

The Real Florida 5K and 10K is an annual cross-country race held at Wekiwa Springs State Park in Apopka, Florida. Celebrating its 39th edition in 2026, the event features an off-road course through scenic natural surroundings. Participants..

Swamp 10k/30k/50k Trail Race, staged in Palm Coast, Florida by East Coast Trail Racing, offers 50K, 50K Relay, 30K, and 10K on rugged single-track trails. The course is described as beautifully challenging, featuring 2,345 feet of elevation..

In the Woods 30A 50K invites solo runners and two or three person relays to tackle sandy trails, creek crossings and pine forest at Point Washington State Forest. Expect rugged single track, scenic views and a finisher medal.