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.

Date	Event	Location	Website	Type
July 12, 2026	40th Annual Cool Sommer Mornings Triathlon	Clermont, FL		Road - triathlon
August 1, 2026	River City Summer Slam	Jacksonville, FL		Road - 22/37/65 miles
August 1, 2026	The Springs Hop Gravel Grind	Mayo, FL		Gravel - 40/60 miles
August 9, 2026	40th Annual Cool Sommer Mornings Triathlon #3	Clermont, FL		Road - triathlon
September 13, 2026	40th Annual Cool Sommer Mornings Triathlon #3	Clermont, FL		Road - triathlon
September 14, 2026	Endless Summer Watermelon Ride	Fernandina Beach, FL		Road - 11/30/52/73/100 miles
October 3-4, 2026	Bike MS - Cycle to the Shore	Ponte Vedra Beach, FL		Road - 36/59/77/100 miles
October 3-4, 2026	Tally Tango Bikepacking Challenge	Tallahassee, FL		Gravel - 165/177/277 miles
October 10-11, 2026	Cycle Mount Dora	Mount Dora, FL		Road - 10/30/43/52/73 miles
October 17, 2026	Bike 5 Cities	Winter Park, FL		Road - 5/10/30 miles
October 17, 2026	Gulf Coast Bike Trek	Dunedin, FL		Paved Trail/Road - 10/25/40/62 miles
October 17-18, 2026	Great Floridian Multisport Festival	Clermont, FL		Sprint Triathlon, Duathlon
October 18, 2026	Women on Wheels (WOW) Ride	Sarasota, FL		Road - 20/40/62 miles
October 18, 2026	Tropical Triathlon	Lake Worth, FL		Sprint Triathlon, Duathlon
October 24, 2026	Spaghetti 100	Miccosukee, FL		Road / Gravel options - multiple distances
October 25, 2026	Intracoastal Waterway Century	Cocoa, FL		Road - 14/28/65/100 miles
November 7, 2026	Hearts for Our Hospital Challenge	The Villages, FL		Road - 10/20/33/63/75 miles
November 7-8, 2026	Round Lake Okeechobee Bicycle Tour	Okeechobee, FL		Paved Path - 114 miles over two days