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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…
Tour de Keys is a unique charity cycling event that takes riders on a breathtaking journey through the Florida Keys. Cyclists can choose either a 100-mile ride from Key Largo or a 50-mile ride from Marathon, both finishing in Key…
Ride and Run with the Stars is an annual charity cycling and running event hosted by the Pinellas County Sheriff’s Office. Now held at Waterfront Park in Safety Harbor, the event raises money for the…
Gran Fondo Sarasota is a charity cycling event that brings riders together to support the Team Tony Cancer Foundation, which provides free peer-to-peer support, resources, and financial assistance for cancer fighters, survivors, caregivers, and their families across…
