Trail Running calendar near Holiday 2026-2027

Hit the Pinellas Trail for a Halloween-themed run supporting veterans. The Camo & Cobwebs event offers a timed 5K and an untimed 1 Mile Fun Run/Walk, both starting and finishing at de Bine Brewing Company. Expect costumes, finisher medals,..

This Halloween trail race offers a spooky evening on the Florida Greenway. Choose from 5k, 10k, or a combined challenge in either run or ruck divisions. Costumes are encouraged, and all finishers get a medal.

An 8K trail race through Weedon Island Preserve on October 24, 2026, featuring natural trails, boardwalks, views of Tampa Bay and professionally timed results; proceeds support Friends of Weedon Island.

Celebrate Halloween with a spooky 5K in Clermont. The evening event features haunted zones, a costume contest, and a live DJ. A virtual 5K option is also available.

Trail run at Lake Louisa State Park on November 7 2026 offering 5K 10K and half marathon across varied trails with aid stations and age group and team awards.

Join this patriotic honor run on the scenic Pinellas Trail to celebrate military veterans. Choose from 10K, 5K, or Kids Dash distances in a stroller friendly environment at Dunedin.

Celebrate Thanksgiving with this family friendly event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip timed results, finisher medals, and festive treats at the finish line.

Savage Race Florida Fall takes place November 14, 2026 in Dade City, Florida, offering two obstacle-course options and rewards for completing multiple courses.

Honor America's veterans at this scenic out and back race along the paved Courtney Campbell Causeway Trail. Choose from multiple timed distances and enjoy panoramic views of Tampa Bay while supporting veteran suicide prevention.

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.

A trail and multi-lap running event in Lutz, FL on December 13, 2025, offering a 4.45 mile race and a seven hour multi-lap 50k option with participant T-shirts and awards.

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.

Sleigh It is a looped event at Lake Wailes Park offering a 5 Mile option plus 6 hour and 12 hour timed formats. The 5 mile loop runs on grass and asphalt with aid stations at each turnaround.

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.