Trail Running calendar near Greater Carrollwood 2026-2027

A 100 mile point to point urban ultramarathon from Ybor City to St. Petersburg. The self guided endurance tour passes Safety Harbor, Dunedin, Clearwater and Gulfport with staffed aid stations, mandatory navigation gear and timed cutoffs.

Experience the natural beauty of Lakeland at Colt Creek State Park for a trail event featuring distances from 14 miles to a 60 mile ultra. Enjoy a loop based course with handcrafted medals and a post race picnic.

Experience the natural beauty of Carlton Reserve at this Florida trail event. Runners can choose between three distances and enjoy a pre race stretch session with recovery snacks and awards for various age groups.

Trail ultraruns at Lake Louisa State Park in Clermont, FL offering 50K and 25K on a 16.2 mile loop with mostly singletrack, varied terrain and about 700 feet of elevation on the 50K. Four aid stations and professional timing are provided.

Experience a team relay through the shaded pine forests and palm trees of Alafia River State Park. Run together in teams of four or eight and enjoy a festive weekend village with campfires and star lit camping.

Celebrate the holidays at the Candy Cane Course in Orlando featuring distances from a Kids Dash to a 15k. Enjoy chip-timed results, designer shirts, finisher medals, and festive treats at the finish line.

Conquer a variety of obstacle courses at Skipper Ranch including 5K, 10K, and 21K distances. Experience a unique terrain of flat farmland and deep marsh mud in the heart of Florida.

Holiday races in downtown Dunedin at HOB Brewing Company offer 5K, 10K (2 loops) and 15K (3 loops) on a paved, timed course along the Pinellas Trail, with medals, event shirts and a post-race beer for participants over 21.

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 trail event at Colt Creek State Park offering a six-loop **100-mile** race and a single-loop **12.5-mile** 100 furlongs course with staffed aid stations, looped drop bag access, and a rollover credit policy.

A free, donation-supported 12 hour trail event at Whispering Pines City Park with a 5 mile loop, an aid station and a finisher award for 10 miles. Capacity is 185 and there is no waitlist.

A 5K and 10K trail run at Lake Manatee State Park featuring sandy paths, pine corridors, wildlife sightings, chip timing, finisher medal, and post-race refreshments. A lodging partner offers a promo code RUN for event dates.

Experience a scenic trail race through the Carlton Reserve in Venice with distances ranging from 5k to 15k. Enjoy post race snacks and unique handmade wood awards in a festive community atmosphere.

Experience a unique single loop trail run through the Withlacoochee State Forest featuring 33 1/3 mile, half marathon, and 6K distances. Enjoy riverside trails and celebrate your finish with a post race barbecue and handcrafted medals.