Events in Florida

Upcoming Cycling Events Across Florida

Road | Gravel | MTB | Triathlons | Gran Fondos

Photo by Horrible 100 Cycling Event

Cycling events usually have multiple distances and ride-at-your-own-pace.  Pick an event and distance to challenge yourself to a new level of fitness.
Search through the listing below by date, event, location and type.

DateEventLocationWebsiteType
August 1, 2026River City Summer SlamJacksonville, FLRiver City Summer Slam 2026Road - 22/37/65 miles
August 1, 2026The Springs Hop Gravel GrindMayo, FLThe Springs Hop Gravel Grind croppedGravel - 40/60 miles
August 9, 202640th Annual Cool Sommer Mornings Triathlon #3Clermont, FLCool Summer Series Triathlon 2026 smallRoad - triathlon
August 23,2026Kids TriathlonPalm Harbor, FLKids Triathlon 2026Road - triathlon
September 6, 2026Manatee TriathlonCape Coral, FLManatee Man Triathlon 2026Triathlon - Sprint/International
September 6, 2026Big Red Chair TriathlonSt. Cloud, FLBig Red Chair Triathlon 2026Triathlon - Sprint/International
September 13, 202640th Annual Cool Sommer Mornings Triathlon #3Clermont, FLCool Summer Series Triathlon 2026 smallRoad - triathlon
September 14, 2026Endless Summer Watermelon RideFernandina Beach, FLEndless Summer Watermelon Ride 2 reducedRoad - 11/30/52/73/100 miles
September 19, 2026Tour de TowBartow, FLTour de Tow 2026Road - 17/35/65 miles
October 3-4, 2026Bike MS - Cycle to the ShorePonte Vedra Beach, FLBike MSRoad - 36/59/77/100 miles
October 3, 2026Bob's Ride for Cancer AwarenessIndian Harbour Beach, FLBobs Cancer Awareness Ride croppedRoad - 10/35/60 miles
October 4, 2026Withlacoochee State Trail RideInverness, FLWithalochee State Trail Ride 2026Paved Trail - 24/44/48/62/100 miles
October 3-4, 2026Tally Tango Bikepacking ChallengeTallahassee, FLTally Tango Gravel 2026Gravel - 165/177/277 miles
October 10-11, 2026Cycle Mount DoraMount Dora, FLCycle Mount DoraRoad - 10/30/43/52/73 miles
October 17, 2026Bike 5 CitiesWinter Park, FLBike 5Road - 5/10/30 miles
October 17, 2026Gulf Coast Bike TrekDunedin, FLGulf Coast Bike Trek logoPaved Trail/Road - 10/25/40/62 miles
October 18, 2026YMCA Youth TriathlonLecanto, FLKids Triathlon 2026Triathlon
October 17-18, 2026Great Floridian Multisport FestivalClermont, FLGreat Floridian MultiSport Festival reducedSprint Triathlon, Duathlon
October 18, 2026Women on Wheels (WOW) RideSarasota, FLWOW Event 2026Road - 20/40/62 miles
October 18, 2026Tropical TriathlonLake Worth, FLBill Bone Tropical TriathlonSprint Triathlon, Duathlon
October 24, 2026Fenner RideMilton, FLFenner RideRoad - 18/45/65/100 miles
October 24, 2026Spaghetti 100Miccosukee, FLspaghetti100 2026Road / Gravel options - multiple distances
October 25, 2026Intracoastal Waterway CenturyCocoa, FLIntracoastal Waterway CenturyRoad - 14/28/65/100 miles
November 7, 2026Hearts for Our Hospital ChallengeThe Villages, FLHearts for our HospitalRoad - 10/20/33/63/75 miles
November 7, 2026Buddy the Bull StampedeArcadia, FLBuddy the Bull 2026MTB - 15K race
November 8, 2026Old Florida GravelLake City, FLOldFloridaGravelGravel - 35/70/100 miles
November 7-8, 2026Round Lake Okeechobee Bicycle TourOkeechobee, FLLake Okeechobee Tour Nov 2026Paved Path - 114 miles over two days
November 14, 2026Ride 4 the AnimalsDunedin, FLRide for the AnimalsRoad - 12/31/55 miles
November 14, 2026Horrible 100 Warm Up RidesClermont, FLHorrible 100 2026Road - 34/42/50 Miles
November 15, 2026Horrible 100Clermont, FLHorrible 100 2026Road - 35/70/100 Miles
November 15, 2026CycleFest 2026Lakewood Ranch, FLCycleFest 2026 Sarasota reducedRoad - 20/35/66 Miles
November 22, 2026Iron Joe Turkey RideNaples, FLIron Joe Turkey RideRoad - 5/10/20/40/62 miles
November 22, 2026Gran Fondo SarasotaSarasota, FLGran Fondo SarasotaRoad - 5/33/62/100 miles
December 5, 2026Kids TriathlonVero Beach, FLVero Beach Kids Triathlon 2026Triathlon
January 3, 2027The Spanish Coast to CoastSt. Augustine, FLSpanish Coast to Coast 2027 reducedUltra Gravel Backpacking
January 24, 2027Tour de CapeCape Coral, FLTour de CapeRoad - 15/30/62/100 miles
January 31, 2027Piggy's RevengeVenice, FLPiggys RevengeGravel and Single Track - 10/20/40/60 miles

Here’s a good resource for finding triathlons throughout Florida – Triathlon Calendar

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