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The 10th Annual BIKE 5 is put on by Bike/Walk Central Florida, BIKE 5 is an annual urban bike tour that traces the "Bike 5 Cities" route, a network of trails, paths, and slow streets connecting cities and neighborhoods across the heart of Central Florida. Now in its 10th year, the event doubles as a…
The 4th Annual Gulf Coast Bike Trek is a fundraising ride hosted by the American Lung Association. The event rolls through historic Dunedin and along the Pinellas Trail, raising money for ALA's lung health research, education, and clean air advocacy. This is a fundraising ride: participants are encouraged to collect donations, not just pay a…
Join women from across the region for the 12th Anniversary WOW Ride, hosted by the Village Idiots Cycling Club of Lakewood Ranch, Bradenton, and Sarasota. Celebrating cycling, community, and America's upcoming 250th birthday, WOW welcomes women of all abilities from first-time event riders to experienced cyclists. Three route options are available: 62-mile Metric Century, 40…
The Fenner Ride is an annual charity cycling event on Saturday, October 24, 2026, starting at 7:30 AM from the Clyde L. Gracey Community Center (5629 Byrom St, Milton, FL). Presented by Big Brothers Big Sisters of Northwest Florida and the West Florida Wheelmen, with all proceeds benefiting BBBS of NW Florida. Four distance options: 18, 44.6,…
41st Annual Spaghetti 100 road and gravel ride hosted by Capital City Cyclists. Five route options starting and finishing at the Miccosukee Community Center, 15011 Cromartie Rd, Miccosukee, FL 32309. Paved routes: Century (101 mi), Metric Century (69 mi), Monticello (32 mi). Gravel/clay routes: Epic Dirt (61 mi), Epicette Dirt (36.5 mi). Routes travel through…
The Intracoastal Waterway Century is hosted by the Spacecoast Freewheelers, a non-profit cycling club. This is a well-supported recreational ride along the scenic Intracoastal Waterway corridor on Florida's east coast. Proceeds benefit local charities. Route Options: Imperial Century — 100 miles Metric Century — 65 miles (100km) Family Fun Rides — 14 or 28 miles…
11th Annual Hearts for Our Hospital Bicycle Challenge is presented by the UF Health Spanish Plaines Hospital Foundation and organized by the Sumter Landing Bicycle Club. This is a fundraiser benefiting UF Health Spanish Plaines…
The inaugural Buddy the Bull Stampede is on Saturday, November 7, 2026 at Eirene Ranch (10531 SW Kissimmee Rd, Arcadia). It's a combo trail run/MTB event with three options: a 5K trail run, a 15K mountain bike race, or…
Old Florida Gravel is a gravel bike/run event at All-Tech Raceway, 1024 SW Howell Rd, Lake City, FL, happening November 7-8, 2026. The vibe is very "backroads Florida" — dirt roads with century-old live oaks…
Ride 4 the Animals is an annual charity cycling event benefiting the Suncoast Animal League. Held at Highlander Park in Dunedin, Florida, the ride offers scenic routes along the Gulf Coast for cyclists of all…
The 46th Annual Horrible Hundred is one of Florida's premier cycling events, challenging riders to conquer the rolling hills of Clermont (some of the state's toughest climbs). Hosted by the Florida Freewheelers, the event offers 35-, 70-,…
CycleFest 2026 celebrates the 50th anniversary of the Sarasota Manatee Bicycle Club's signature cycling event. Riders can choose from 20-, 35-, or 66-mile scenic routes through Sarasota and Manatee counties, with all proceeds benefiting local bicycle-related charities. Registration includes a…
