June 2026

June 13	Wheels & Wings - Gravel Grinder
	TBA mile options
	Peace River Riders
	Cecil Webb WMA - Punta Gorda, FL
	https://wheelsandwings.raceroster.com/

June 14	Wheels & Wings Flag Day Ride
	62, 50, 31, 15 mile options
	Peace River Riders
	Punta Gorda, FL
	https://wheelsandwings.raceroster.com/

October 2026

Oct 17	Gulf Coast Bike Trek
	62, 40, 25 mile options
	American Lung Association
	Dunedin, FL
	https://cycleforair.lung.org/gcbt

Past Events
Planning for the future? Most events return annually, so here's some to watch for in the future.

April 2026

Apr 11-16	Florida Bicycle Safari
	Six days of riding in beautiful North Florida
	Florida Freewheelers
	Live Oak, FL
	https://floridabicyclesafari.com/

Apr 19	GFNY Miami 2026
	70.7 (race) 35.5 (ride) mile options
	Gran Fondo NY
	Miami, FL
	https://miami.gfny.com/

Apr 26	22nd Sharky's Ride the Beaches
	63, 35, 15 mile options
	Sharky's On the Pier Team Tony Cancer Foundation Livestrong Foundation Friends of the Legacy Trail
	Venice, FL
	https://raceroster.com/events/2026/114730/22nd-annual-sharkys-ride-the-beaches-event

March 2026

Mar 1	Naples Bike Brunch
	62, 30, 20, 10, 5 mile options
	Naples Pathways Coalition
	Naples, FL
	https://www.bikesignup.com/Race/FL/Naples/NaplesBikeBrunch

Mar 7	Dirty Pecan 2026 - gravel
	40, 60, 80, 100, 150, 200 mile options
	Benefits Jefferson Ctny 4-H
	Monticello, FL
	https://www.dirtypecan.com/

Mar 21	Pedal and Play
	62, 30, 15, 10 mile options
	TEAM Punta Gorda
	Punta Gorda, FL
	https://teampuntagorda.org/pedal-and-play-in-paradise-2/

Mar 22	Tour de Parks
	62, 35, 21 mile options
	Friends of the Legacy Trail
	Venice, FL
	https://friendsofthelegacytrail.org/tour-de-parks-bicycle-ride/

Mar 28	Bike MS Suncoast Challenge
	100, 75, 50, 22 mile options
	The National Multiple Sclerosis Society
	Lakewood Ranch, FL
	https://events.nationalmssociety.org/bike-ms-bradenton-fl-2026

February 2026

 

Feb 14	Ride for Tiny Town
	60, 45, 35, 20 (e-bikes), 10 mile options
	DeSoto Cares Homeless Services
	Arcadia, FL
	https://www.ridefortinytown.com/home

Feb 14-15	Bike Sebring Time Trial
	6hr, 12hr, 24hr options
	Ultracycing Events
	Sebring, FL
	https://www.bikereg.com/2026-bike-sebring

Feb 15	6th Annual Jean Heuschen Memorial Ride
	30, 60, 100 mile options
	Naples Velo
	Naples, FL
	https://www.naplesvelo.com/jh-memorial-ride.html

 

Feb 15	Suwannee Sweetheart Ride
	100, 62, 52, 25 mile options
	Suwannee Bicycle Association
	White Springs, FL
	https://raceroster.com/events/2026/113789/suwannee-sweetheart-ride-2026

Feb 21-22	28th Annual Royal Palm Challenge
	Saturday - 30, 20 mi gravel Sunday - 62, 44, 21mile road options
	Caloosa Riders Bicycle Club
	Fort Myers, FL
	www.royalpalmchallenge.org

January 2026

Jan 17-18	Giro d'Italia Ride Like a Pro
	Race & Fun Ride options
	LJ Cycling & DRC Sports Athletic Event Management
	Miami, FL
	https://giroridelikeapro-usa.com/

Jan 25	Tour de Cape
	100, 60, 30, 15 mile options
	City of Cape Coral
	Cape Coral, FL
	https://www.tourdecape.net/

Jan 25	Piggy's Revenge
	60, 40 MTB, 20, 10 gravel mile options
	SCORR - Sarasota County Off-Road Riders
	Venice, FL
	https://www.bikereg.com/71724

December 2025

 

Dec 6	11th Annual Hilly Hundred
	100, 68, 32 mile options
	Crank Works Bicycles
	Brooksville, FL
	https://raceroster.com/events/2025/108208/hilly-hundred-2025

 

November 2025

Nov 8	10th Annual Hearts for our Hospital Bicycle Challenge
2025	100, 63, 33, 20, 10 mile options
	UF Health Spanish Plaines Hospital Foundation
	The Villages, FL
	https://heartsforourhospital.raceroster.com/

Nov 9	15th Annual Florida Cycle for Life
2025	100, 68, 36, 23 mile options
	Cystic Fibrosis Foundation
	DeLand, FL
	https://fundraise.cff.org/FLCycle15/

Nov 15-16	The 45th Annual Horrible Hundred
2025	100, 70, 35 mile options
	Florida Freewheelers
	Clermont, FL
	https://horrible-hundred.com/

Nov 15	Ride 4 the Animals
	64, 55, 31, 12 mile options
	Suncoast Animal League
	Dunedin, FL
	https://ride4theanimals.raceroster.com/

Nov 22	Tour de Keys
	100, 50 mile options
	Supports charities MARC House & AH Monroe
	Key Largo or Marathon, FL
	https://tourdekeys.donordrive.com/

Nov 23	Gran Fondo Sarasota
	100, 62, 33, 5 mile options
	Team Tony Cancer Foundation
	Sarasota, FL
	https://teamtony.org/gran-fondo-sarasota/

Nov 30	Iron Joe Turkey Ride & Walk
	62, 40, 20,10, 5 mile options
	Naples Pathways Coalition
	Naples, FL
	https://www.bikesignup.com/Race/FL/Naples/IronJoeTurkeyRide