Save-the-Date: Bike 5 Cities 2021 to Kick Off Mobility Week – Oct. 30

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.

Registration will open soon. To be first in line to register, send us a message to [email protected] if you aren’t already on the email list. Past riders will automatically be added to the pre-registration email. 


Bike 5 Cities is an inclusive, 28-mile slow-paced bike ride to show people of all ages and biking abilities where they can feel most comfortable riding a bike through the neighborhoods in Winter Park, Eatonville, Maitland, Casselberry and Orlando.

Two Ways to Roll: 1) Small Group Guided or 2) Self-Guided

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. 


For the Guided, Small Group Ride, choose from one of the five host city locations. For the Self-Guided Ride, you have a choice of two cities to start the ride: Winter Park and Casselberry.

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 ten 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 was for those who wanted to avoid riding in any size group, prefer a faster pace or just wanted start, stop and rest time flexibility. Self-guided ride was limited to 25 riders.

  • Staggered start times to socially distance
  • Choice of two start locations: Winter Park or Casselberry.
  • Route marked with wayfinding 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.


Sponsorship Opportunities

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








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