Bike 5 Cities 2021

Pump up your tires and save the date for Bike/Walk Central Florida’s signature 28-mile ride: the 5th Annual Bike 5 Cities. This year’s event returns on October 30, 2021, to kick-off FDOT’s Mobility Week. Riders will once again roll through the cities of Orlando, Winter Park, Maitland, Casselberry, and the town of Eatonville. Bike 5 Cities shows riders of all levels where they can comfortably ride on urban routes and trails in Central Florida.


Bike 5 Cities is an inclusive, 28-mile bike ride to show people of all ages and bicycling abilities where they can comfortably ride in Winter Park, Eatonville, Maitland, Casselberry and Orlando.

THREE Ways to Roll: 1) Small Group Guided or 2) Self-Guided 3) Family-Friendly Ride

Last fall, Bike 5 Cities added COVID-19 safety guidelines, such as setting a registration limit, spreading out the starting locations, staggering the start times, offering guided, small group rides and restricting the self-guided ride spots. Participant feedback showed that riders loved the choice of small group guided or self-guided rides, so Bike 5 Cities will continue that ride format this year as well. Plus, we’ve added a five-mile, family-friendly ride!


For the Guided, Small Group Rides and the Self-Guided Rides, choose from one of the five host city locations. The Family-Friendly Ride will start at Cady Way Pool. 

Mead Garden in Winter Park
Community Park in Maitland
Druid Park in Orlando

Town Hall in Eatonville
Wirz Park in Casselberry

The Guided, Small Group Ride gives small ride groups the chance to bike with an experienced ride leader who personally guides you along the Bike 5 Cities route, helping the group maintain proper social distancing at rest stops, red lights, stop signs, etc. Each small group decides a comfortable pace for the ride.

  • No more than 15 people per small group, plus an experienced ride leader guide.
  • Staggered start times, scheduled in 15 minute increments.
  • Groups registered to begin from one of five designated start locations: Winter Park, Eatonville, Maitland, Casselberry and Orlando.
  • Snacks and bottled water provided at each of the five city stops.

The Self-Guided Ride offered all the benefits and support of the guided, small group ride, but without a ride leader. This option is for those who want to avoid riding in any size group, prefer a faster pace or just want start, stop and rest time flexibility. 

  • Staggered start times between 7:30 – 8:30 a.m. to socially distance.
  • Choice of start location.
  • Route marked with way-finding signs for the 28-miles.
  • Route map accessible via Ride with GPS app or a cue sheet available at start location.
  • Mandatory face covering at the start, all stops, crowded locations, and where not possible to maintain a minimum 6-feet distancing. See COVID-19 Guidelines.
  • Snacks and bottled water provided at each of the five city stops.

NEW THIS YEAR: Family Friendly Guided Ride: 

Bring your family (kids included) to this year’s new Family Ride. Start at the Cady Way Pool and ride down the Cady Way Trail around Lake Baldwin Park. Ride leaders and other support volunteers will help guide families (parents must supervise their kids) for a fun filled experience on our trails! 
–One large group ride with families and kids 
–Leaves the Cady Way Pool at 10:00am and will return back 
–Ride leaders and extra volunteers will take pictures, assist parents and kids and help guide the group down the trail, teaching everyone how to be safe and courteous 
–Only $7.50 per rider 

Sponsorship Opportunities

If your organization is interested in sponsorship opportunities for the 2021 Bike 5 Cities, please contact Emily Hanna at mailto:[email protected]



If you have further questions about this ride, contact us at [email protected]