Skip to main content

Interested in cycling but not sure where to start? Join us Saturday May 5, 2018 as we explore Central Florida's bike-friendly routes and trails.

This 28-mile guided ride through Orlando, Winter Park, Casselberry, Maitland and Eatonville provides an excellent opportunity to explore Central Florida by bike.

Shorter, family-friendly rides, fun activities, games and refreshments are also provided in each of the host cities.

Riders are encouraged to set their own pace and distance.

Presented by 

Florida Department of Transportation's  
"Alert Today Alive Tomorrow" initiative 

Event t-shirts only for the first 300 registrants for the 5-Cities Ride or until each size is depleted.

T-shirts will not be shipped to those that do not pick them up at registration.

Bike 5 Cities Route SOLD OUT!  Thank You!

Bike 1 City Registration Still Open!

We are still accepting Donations!
Click Here to Donate!

Registration fees

Bike 1 City - Registration Free | Donations Welcome Closed

Select from Orlando, Winter Park, Casselberry, Maitland & Eatonville

  1. Free
    Mar 8 - May 5

Route Options

Bike 5 Cities

8:00 am

Start Location
Mead Botanical Gardens
1500 S. Denning Dr, Winter Park, FL

Begins in Mead Garden in Winter Park and rolls thru Orlando with stops to rest in Orlando, Winter Park, Casselberry, Maitland and Eatonville before returning to Mead Garden for a total distance of 28 miles. 

Distance:  28 miles
See route here. 


City Events

8:30 am

Start Location 
Lake Druid Park, 899 Coy Drive, Orlando, FL

Come and enjoy Orlando’s Urban Mountain bike park with a pump track, junior pump track and single-track trail.  The park also features a fenced dog run and community garden.   

Distance: Your choice!  All onsite at the park!


9:00 am

Start Location
Cady Way Pool Trailhead, 2525 Cady Way, Winter Park, FL

Ride the Cady Way trail together toward Baldwin Park. The route is an out and back on the trail so you can choose your own distance. 

Distance: 5.5 miles
See Route here


10:00 am

Start Location
Wirz Park, 806 Mark David Blvd, Casselberry, FL

Ride the Casselberry Greenway Trail – The ride is an out and back on the trail so you can choose your own distance.

Distance: 5.9 miles
See Route here  

10:30 am

Start Location
Maitland Community Park, 1400 Mayo Ave, Maitland, FL

Ride thru the Dommerich Neighborhood with a police escort – 5 miles total but easy to head back on your own. 

Distance: 4.3 miles
See Route Here

11:00 am

Start Location
Town Hall, 307 E. Kennedy Blvd, Eatonville, FL

Ride around the Town of Eatonville with a police escort in one of central Florida’s most comfortable communities to ride a bicycle.

Distance: 2.5 miles
See Route Here

Register Early!


Want to Volunteer?

Want to Volunteer? 
Text or Email Lisa Portelli, BWCF Board Member, 407-961-9225‬‬ or 

We need Ride Leaders to roll ahead of the group,
Ride Marshalls to coach and guide the paceline and day-of-event volunteers.

Weather Cancellation Policies

This is a Rain or Shine event.  No refunds or transfers.

The safety of our participants and volunteers is our most important concern and if any of the threatening weather conditions are present the day of the event (tornado warning, tornado watch, thunderstorm, heavy rain or a hurricane decides to visit), the event may be delayed or canceled. 

When weather conditions or other physical conditions present a danger to participants, such conditions fall under the label “acts of mother nature,” it will not result in refunding of any event entry fees or future event credits, since funds were already spent in preparation for your event day.

Event Schedule

  • May 5 8:00 AM EDT - Bike 5 Cities - Start at Mead Garden

  • May 5 8:30 AM EDT - Bike Orlando Pit Stop

  • May 5 9:00 AM EDT - Bike Winter Park Family-Friendly Ride

  • May 5 10:00 AM EDT - Bike Casselberry Family-Friendly Ride

  • May 5 10:30 AM EDT - Bike Maitland Family-Friendly Ride

  • May 5 11:00 AM EDT - Bike Eatonville Family-Friendly Ride

  • May 5 12:00 PM EDT - Event Day Ends in Mead Garden

Contact Information

Event Location

Mead Botanical Garden, South Denning Drive, Winter Park, FL, USA

Click here to view map