Upcoming trail running races in and near Winter Garden, Florida. Use filters to quickly find races by month or distance.
More races: USA running calendar
Date Race Distance Location hf:tax:distancecategory hf:tax:monthandyear 11/09/2024 The Florida Run at Louisa State Park Half Marathon 10K, 13.1M, 5K Clermont FL 10k 5k half 11-november 07/20/2024 Skunk Ape Night Run 30K Dade City FL half-marathon-to-full-marathon 07-july 11/23/2024 Colt 45 Trail Run 14M, 45K, 45M, 60M Lakeland FL ultra 11-november 03/01/2025 Long Play Trail Run Half Marathon 13.1M, 33.3M, 6K Brooksville FL 10k half ultra 03-march 11/24/2024 Cupcake Race @ Hawthorne Trail 10K, 13.1M, 26.2M, 5K Hawthorne FL 10k 5k half marathon 11-november 08/31/2024 Pinellas Trail Challenge 46M Saint Petersburg FL ultra 08-august 07/13/2024 Vero Beach Octopus Ultra 100K, 100M, 50K, 50M Vero Beach FL ultra 07-july 12/14/2024 The Daytona 100 Ultra 100M, 50K, 50M Jacksonville FL ultra 12-december 02/15/2025 Lost 118 100K, 118M Clewiston FL ultra 02-february