Trail Running calendar near Greater Carrollwood 2026-2027

A 30K trail race at Green Swamp West Tract near Dade City, FL, featuring varied Florida terrain, aid stations every 3 to 5 miles, a Berm drop bag location, finisher glassware awards, and a post-race potluck.

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.

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 six-hour Fat Ass running event at Walsingham Park in Seminole, FL on August 1, 2026. Runners self record laps on a roughly 3 mile paved out and back loop; the event is self supported and free with voluntary cash donations.

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.

An 8 Hour timed ruck event at Ross Prairie Trailhead near Dunnellon, FL featuring a 6.5 mile loop across berm roads and sandy trails. Combat Racing Events offers rucking divisions with enforced minimum pack weights and on site camping.

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.

Wild Boar Night Run on September 12, 2026 is a half marathon and half marathon ruck in Green Swamp West Tract near Dade City, FL. The out-and-back trail is marked with pink flags, has an aid station at the turnaround, and a post-race potluc..

Trail run at Central Florida Bible Camp in Eustis with a roughly 3.2 mile two loop option and a single loop fun option. Runners can attempt up to ten field day stations such as inflatable obstacles, axe throwing, and cornhole.

Tick Tock Ultra on September 19, 2026 offers timed running formats including 12 hour, 6 hour, and a 12 hour five person relay, organized by Ultra Ultras.

Tick Tock Ultra is a lake-lap timed event at Lake Hollingsworth in Lakeland, FL offering 12-hour and 6-hour individual races plus a 12-hour relay for teams of 3 to 5; portions of entries support the Pheel Good Foundation.

A multi distance running event in Tampa with a half marathon, 10K, 5K, 1 mile, kids dash and virtual option. Features include chip timing, designer shirts and finisher medals, with youth pricing for ages 12 and under.

A community 5K/10K/15K on the Pinellas Trail in downtown Dunedin at HOB Brewing Company on September 27, 2026, with electronic timing, finisher medals and a post-race party including one free draft beer for participants 21 and over. The eve..

A race day at Jay Blanchard Park on 09/27/2026 with distances from a 50 m kid's dash to a 13.1 mile half marathon, chip timing for main races, event shirts and medals, plus volunteer and virtual options.

The John Holmes Trail Run takes place at Croom Park and Withlacoochee State Forest on October 3, 2026, offering 50K, 16 mile and 9 mile options. The field is limited to 250 runners and this is the event's 34th running.

A timed climb of 861 steps to the rooftop of Tampa City Center with official timing to the 39th floor, bailout floors, water stations and on site medics.

Orlando Spartan Weekend at Lake Nona offers multi-format obstacle course races on October 10 and 11, 2026, including Sprint, Super, kids races, an obstacle workshop, and a four hour Hurricane Heat.

A Halloween themed trail event in Englewood on October 17, 2026 featuring a 5K run and a 1 mile walk, costume awards, finisher medals, post-race refreshments, and proceeds supporting the Zoomers Scholarship Fund.

A Halloween themed 5K and 1 Mile Fun Run on October 17 2026 along the Pinellas Trail supporting Club-214 Land & Sea. Proceeds fund veteran services; participants receive finisher medals and costume prizes.

A dog friendly off-road 5K at Rock Springs Run State Reserve in Sorrento, FL on October 24, 2026. Registration includes park admission, a t-shirt and finisher medals for runner and dog, with limited in-person spots.