FloridaBicycling.com

Endless Summer Watermelon Ride
2026-09-13 07:30 - 16:00 (America/New_York) | Atlantic Recreational Center, Atlantic Avenue, Fernandina Beach, FL, 32034, United States
Presented by the North Florida Bicycle Club and the Major Taylor Cycling Club of North Florida, this is a long-running recreational cycling event now in its 37th year. It’s a non-competitive, supported ride open to cyclists of all levels, taking place on open public roads around Fernandina Beach/Amelia Island.
Route Options Five distances to choose from:

100 miles — Mighty Melon Century
73 miles — Big Melon Metric Century Plus
52 miles — Half Melon Half Century
30 miles — Le Petit Melon
11 miles — Tour de Fort Family Fun Ride

What’s Included Pre-ride snacks, fully stocked rest stops (food, water, Gatorade, and Pickle Juice), route markings, mechanical support, SAG vehicles, and a post-ride lunch. Registered riders also get a commemorative t-shirt and personalized number bib, with an option to have your event packet mailed to you before race day.
Beneficiary A portion of proceeds supports the NFBC’s Pedaling for Safety campaign, which works to reduce cyclist fatalities and injuries along Florida’s First Coast.

Tour de Tow
2026-09-19 07:00 - 14:00 | Front Page Brewing, 190 S Florida Ave, Bartow, FL
The Tour de Tow is a scenic road tour featuring a 17-mile family fun ride and 35-mile and 65-mile road tours. Ride along and experience the tranquil countryside, and settle into some hometown cycling hospitality on the return to Bartow.

Bob's Ride for Cancer Awareness
2026-10-03 07:00 - 14:00 | Bob’s Bicycle Shop, 510 E Eau Gallie Blvd, Indian Harbour Beach
This is the 19th edition of Bob’s Ride for Cancer Awareness. It’s a road ride with 10-, 35- and 60-mile routes. Ride for our Mothers, Fathers, Daughters, Sisters, Aunts, customers and best friends. Ride for people we know and for people we don’t. Rde to raise money to help people in need. For the 19th year, the ride supports breast cancer awareness and treatment with 100% of the ride registration fees going directly to this worthy cause.

Bike MS - Cycle to the Shore
2026-10-03 07:00 - 2026-10-04 17:00 | PGA TOUR Headquarters, 5380 Palm Valley Road, Ponte Vedra Beach, FL, 32082, United States
A two-day fundraising cycling event hosted by the National MS Society, raising money toward a cure for multiple sclerosis. Route options range from 36 to 100 miles and are designed for both new and veteran cyclists.
Riders start at either PGA TOUR Headquarters or Marineland, then make their way south along the A1A to Daytona Beach for a beachside celebration. Day 2 is a return ride back to the respective start lines.
This is a fundraising ride, not a registration-fee event — participants are expected to meet a fundraising minimum (historically $275) to pick up their packet. Support includes rest stops, SAG vehicles, bike mechanics, and medical support along the route.

Tally Tango Bikepacking Challenge
2026-10-03 07:00 - 2026-10-04 23:59 | Weems Road Mini Trailhead, 3430 Weems Road, Tallahassee, FL, 32317, United States
Hosted by Singletrack Samurai, The 12th Tally Tango Bikepacking Challenge 2026 is the premier bikepacking event in the Florida panhandle. Four ultra-endurance self-supported routes depart from the Tallahassee trail network and wind through singletrack, gravel double-track, coastal levees, and forest roads:

Tango Original 165 — 165 miles, bypasses Aucilla
Tango 177 — along the Aucilla River, with access to some of Florida’s only whitewater rapids
Tango 277 — the 177 route extended through Tate’s Hell State Forest (~277 miles)
Tango LiTe — ~230 miles, mostly gravel, avoids 99% of singletrack (not easy)

This is a true self-supported ITT. There is no SAG, no pre-arranged support, riders must carry themselves and resupply from commercial sources only. GPS tracking via Trackleaders is required for those who want their times recorded. Registration (~$76) covers route files, a GPX track, waypoint resource file, and a commemorative patch. Route info is sent August 1.

Withlacoochee State Trail Ride
2026-10-04 07:00 - 16:00 | The Depot, 218 N Apopka Avenue, Inverness, FL, 34450
Join the Friends of the Withlacoochee State Trail for the Annual Preservation Ride! This event brings together cyclists and community members dedicated to protecting and preserving the Withlacoochee State Trail. By riding, you’ll help keep the wheels turning for ongoing trail preservation, ensuring that the trail remains safe, scenic, and accessible for all. Be a part of the movement and help sustain the beauty and vitality of the trail for generations to come.
Century, Metric Century, 48 Mile, and 24 Mile Rides are available.

Cycle Mount Dora
2026-10-10 07:00 - 2026-10-11 15:00 | Gilbert Park, 310 S. Tremain St., Mount Dora, FL, 32757
The 52nd Annual Cycle Mount Dora is a two-day road cycling event on October 10–11, 2026, starting at Gilbert Park (310 S. Tremain St) in Mount Dora. Saturday offers four route options — 10, 34, 52, and 73 miles — including the signature Conquer Sugarloaf Mountain challenge. Sunday has three routes at 10, 30, and 43 miles. Both days start at 7:30 AM.
Registration covers both days and includes a commemorative t-shirt, finisher medal, post-ride lunch each day, fully stocked rest stops, on-course mobile support, and route markings. Packet home delivery is available through September 27. Camping is available nearby at Trimble Park. It’s a rain-or-shine event with no refunds.

10th Annual Bike 5 ride
2026-10-17 07:30 - 14:00 | Mead Botanical Garden, 1500 S Denning Drive, Winter Park, FL, 32789, United States
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 fundraiser for BWCF’s year-round education and advocacy work promoting safer streets, protected bike lanes, and trail connectivity.
This isn’t a traditional timed ride or a charity century. The focus is on showcasing how existing active transportation infrastructure connects communities, with routes designed to highlight trails, neighborhood streets, and main corridors that reflect real-world everyday travel. Shorter, community-oriented routes and longer endurance options are both available.
What’s included with registration:

BIKE 5 t-shirt and wristband
SAG vehicle support and bike mechanics on route
Refreshment stops with food, drinks, and restrooms
Route maps with navigation
Giveaways

Gulf Coast Bike Trek
2026-10-17 07:30 - 15:00 | John R. Lawrence Pioneer Park, 420 Main Street, Dunedin, FL, 34698, United States
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 registration fee.
There ar four route options, all fully supported with rest stops and hydration stations, the majority on trail:

Metric Century — 62 miles, for intermediate to advanced cyclists
40-Mile Ride — scenic Gulf Coast routes, suitable for most cyclists
25-Mile Ride — new for 2026, along the Pinellas Trail
Alpha-1 Foundation 10-Mile Family Ride — leisurely, all ages and abilities welcome

All proceeds support the American Lung Association’s mission to improve lung health and prevent lung disease.

12th Annual Women on Wheels (WOW) Ride — Stars, Stripes & Spokes
2026-10-18 08:00 - 12:00 | Sarasota Farm Bureau, 7289 Palmer Blvd, Sarasota, FL
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 miles, and 20 miles.
Saturday Night Social features Amanda Coker, Guinness World Record holder for the greatest distance cycled in one year (86,573 miles).
Proceeds benefit Selah Freedom, helping survivors of sex trafficking through prevention, outreach, and restoration programs.

Fenner Ride
2026-10-24 07:00 - 16:00 | Clyde L. Gracey Community Center, 5629 Byrom Street, Milton, FL, 32570
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, 64.5, and 100.3 miles, all routed from historic Milton into the Blackwater Forest and back along the Blackwater Heritage State Trail. Fully supported with rest stops, limited sag support, and a post-ride Sonny’s BBQ meal. T-shirts guaranteed for registrations by October 1.

The ride is dedicated to the memory of two cyclists — Dr. Fenner McConnell, killed by a hit-and-run driver in 1998, and Matt Wantz, both former West Florida Wheelmen members.

41st Annual Spaghetti 100
2026-10-24 07:00 - 17:00 | Miccosukee Community Center, 15011 Cromartie Road, Miccosukee, FL, 32309, United States
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 historic Thomasville and Boston, GA and Monticello, FL. Well-stocked rest stops, mechanical/medical/SAG support. Proceeds fund the Kids on Bikes program supporting bicycle safety education in Leon County schools.

Intracoastal Waterway Century
2026-10-25 08:00 - 18:00 | Cocoa Civic Center, 430 Delannoy Avenue, Cocoa, FL, 32922, United States
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

Pricing:

Early registration (through July 26): $60 centuries / $45 family rides
Regular (through Oct 11): $65 / $50
Late (through Oct 24): $70 / $60
Day of (Oct 25): $80 / $65
Group/team discount: 10% off for 4+ riders (online only)
SCFW member discount also available online

What’s Included: Light breakfast before the ride, five fully stocked rest stops, roving SAG with mechanical support, rider insurance, cue sheets and maps, well-marked routes, and a hearty dinner after the ride. T-shirt guaranteed if registered by September 30. Packets can be mailed to registered riders in advance.

Hearts for Our Hospital Bicycle Challenge
2026-11-07 07:30 - 16:00 | Savannah Center, 1545 N Buena Vista Boulevard, The Villages, FL, 32162, United States
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 Hospital — supporting capital equipment purchases and medical scholarships of up to $2,000 per student. Signature sponsor is UnitedHealthcare. Part of the CAAM Events Cycling Series.
Five Route Options (staggered starts, all color-coded):

75 miles — Full Arrest (7:30 AM)
63 miles — Quadruple Bypass Metric Century (7:45 AM)
33 miles — Triple Bypass Half Metric Century (8:00 AM)
20 miles — Double Bypass Quarter Century (8:30 AM)
10 miles — Nitrous Oxide Fun Ride (9:00 AM)

Pricing:

20–75 mile routes: $60 early (through Aug 9) / $65 regular / $70 late / $80 day-of
10-mile fun ride: $25 (all tiers) / $35 day-of

What’s Included: Pre-ride light breakfast, commemorative t-shirt, personalized number bib, fully stocked rest stops, on-course mobile support, route markings, and post-ride lunch. Packet home delivery available through October 25. Custom jerseys and bibs are available to pre-order separately via Primal.

Buddy the Bull Stampede
2026-11-07 08:00 - 13:00 | Eirene Ranch, 10531 SW Kissimmee Rd, Arcadia, Florida, 34269
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 the “Stampede Challenge” doing both back-to-back. Spots are very limited — 150 for the run, 50 for the MTB.

Post-race festivities include breakfast from Rose Cafe & Bakery, Tally Roe coffee, sourdough cookies, Charlie Foxtrot beer, live music, yard games, and a meet-and-greet with the mascot Buddy the Bull. All proceeds benefit Eirene Ranch, which provides Equine Assisted Learning for trauma survivors.

Old Florida Gravel
2026-11-08 07:00 - 17:00 | All-Tech Raceway, 1024 SW Howell Rd, Lake City, FL, 32024
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.

Gravel rides: 35, 70, and 100 mile options ($115–$145)

5K Gravel Run ($30)

Redline Relay — 4-6 person team event ($265)

Kids Events — Strider Sprint (3-6), Rally Ride (6-8), Dirt Drift (9-12) ($20–$25)

The vibe is very “backroads Florida” — dirt roads with century-old live oaks draped in Spanish moss, clear springs near the venue, and roadside fruit stands along the route. Registration is through RunSignup, with additional details on the race’s own site at clashendurance.com.

Ride 4 the Animals
2026-11-14 08:00 - 14:00 | Highlander Park & Aquatic Complex, 1937 Ed Eckert Drive, Dunedin, fl, 34698
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 skill levels, with distance options ranging from a family-friendly 12-mile ride to a challenging 55-mile half-century. Registration includes well-stocked rest stops, on-course support, a post-ride lunch, and a commemorative T-shirt for early registrants. All proceeds help support the rescue, rehabilitation, and adoption efforts of the Suncoast Animal League.

Horrible 100 Ride and Fitness Expo
2026-11-14 10:00 - 2026-11-15 17:00 | Clermont Waterfront Park, 330 3rd St, Clermont, FL, 34711
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-, and 100-mile routes with fully supported rest stops, SAG support, police assistance, and a post-ride lunch. The weekend also features a Cycling & Fitness Expo, making it a favorite destination for cyclists looking to test themselves on Florida’s most famous “mountains.”

The Cycling and Fitness Expo takes place on Saturday, Nov. 14 from 10 a.m. to 5 p.m.

CycleFest 2026
2026-11-15 07:30 - 15:00 | Main Street at Lakewood Ranch, 8100 Lakewood Main St., Lakewood Ranch, FL, 34212
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 light breakfast, fully stocked rest stops, SAG support, a post-ride lunch, and a commemorative event cap. The ride takes place on Sunday, November 15, 2026, starting from Main Street in Lakewood Ranch.

Tour de Keys
2026-11-21 07:00 - 15:00 | Gulfside Village Shopping Cente, 5800 Overseas Hwy., Marathon, Florida, 33050
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 West. The event supports MARC, a nonprofit that empowers adults with developmental disabilities in the Florida Keys, making every mile ridden a meaningful contribution to the community. Participants enjoy fully supported routes, scenic ocean views, rest stops, SAG support, and a festive finish-line celebration in Key West.

Ride and Run with the Stars 2026
2026-11-21 08:00 - 17:00 | Safety Harbor Waterfront Park, 105 Veterans Memorial Ln, Safety Harbor, Florida, 34695
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 Sheriff’s Christmas Sharing Project, which provides food, clothing, toys, books, and other necessities to Pinellas County families in need. The 2026 event is scheduled for November 21. (pinellassheriff.gov)

Routes include 62-, and 10-mile bike rides, a 10k and 5k run and a 1-mile fun run.

Gran Fondo Sarasota
2026-11-22 07:00 - 15:00 | Sarasota Farm Bureau, 7289 Palmer Blvd, Sarasota, FL
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 Florida’s Suncoast. Cyclists can choose from 5-, 33-, 62-, or 100-mile routes, all fully supported with rest stops, SAG support, breakfast, lunch, and an energetic finish-line celebration. Every registration helps fund Team Tony’s mission to ensure that no one faces cancer alone.

Iron Joe Turkey Ride
2026-11-22 07:30 - 14:00 | Eagle Lakes Community Park, 11565 Tamiami Trail E, Naples, FL, 34113
ron Joe Turkey Ride & Walk is a Thanksgiving weekend cycling tradition in Naples that offers a fun, family-friendly ride supporting the Naples Pathways Coalition and its mission to promote safe biking and walking throughout Southwest Florida. Riders can choose from 62-, 40-, 20-, 10-, or 5-mile routes, with a shorter family ride option inside the park, plus walking routes for non-cyclists. The event features breakfast, rest stops, SAG support, a post-ride lunch, music, raffles, and a festive community atmosphere at Eagle Lakes Community Park.

Breakthrough T1 Ride
2026-12-03 08:00 - 2026-12-06 17:00 | Omni Amelia Island Resort, 39 Beach Lagoon Rd, Fernandina Beach, FL, 32034
Breakthrough T1D Ride, Amelia Island 2026 is a multi-day fundraising cycling event hosted by Breakthrough T1D raising money for type 1 diabetes research. The Amelia Island edition takes riders through the natural beauty of Northeast Florida, flat roads canopied with Spanish moss, ocean views, pristine beaches, marshlands, and maritime forests.
Route options go up to 100 miles, making it accessible to cyclists of all levels. The event spans four days and is structured as a destination ride experience with package-based registration covering airfare, lodging, bike shipping, and other perks depending on the package chosen.
This is less a traditional century ride and more a curated multi-day event weekend built around community and fundraising. Riders set personal fundraising goals, earn exclusive swag based on what they raise, and participate alongside a tight-knit T1D community. Coaches and volunteers are also welcome to register in non-riding roles.

Clash Endurance Redline Relay
2026-12-05 13:30 - 17:00 | Daytona International Speedway, 1801 W International Speedway Blvd, Daytona Beach, Florida, 32214
The Redline Relay is a two-hour team cycling race on the iconic oval at Daytona International Speedway. Teams of 3–8 riders compete to complete the most laps, with two riders from each team on the track at a time. Riders make exchanges in their assigned NASCAR pit stall, and each team member must complete at least one lap. Drafting is permitted, making teamwork and strategy a big part of the race.

For 2026, the race is Saturday, December 5 at 1:30 p.m. The event uses road bikes only—no TT bikes or e-bikes—and aerobars are prohibited. Teams are grouped as 3–4, 5–6, or 7–8 riders.

Tour de Cape
2027-01-23 06:30 - 2027-01-24 15:00 | Rotary Park, 5505 Rose Garden Rd., Cape Coral, FL, 33914
The Tour De Cape is one of Southwest Florida’s premier cycling weekends, held annually in Cape Coral. Hosted by the Cape Coral Parks and Recreation Department, the event features a timed 5K run/walk, a kids’ bike ride, and scenic cycling routes of 15, 30, 62, and 100 miles through the city’s northwest and southwest neighborhoods. Riders enjoy fully supported routes with rest stops, SAG vehicles, police support, and post-ride festivities, making it a fun and family-friendly event for cyclists and runners of all ages.

Piggy's Revenge
2027-01-31 07:00 - 16:00 | T Mabry Carlton Jr Reserve, 1800 Mabry Carlton Pkwy, Venice, FL, 34292
Piggy’s Revenge is one of Florida’s premier off-road endurance cycling events, held each winter at the scenic T. Mabry Carlton Reserve in Venice. Hosted by Sarasota County Off Road Riders (SCORR), the event offers challenging 10-, 20-, 40-, and 60-mile mountain bike and gravel routes featuring winding singletrack, rugged terrain, and a fun, festival-like atmosphere complete with well-stocked SAG stops, post-ride food, and refreshments. With a limited field of 350 riders, Piggy’s Revenge has become a favorite for cyclists looking to test their endurance while enjoying some of Florida’s best off-road trails.
