Bike 5 Cities Event

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Discover Comfortable Riding Routes on ‘Bike 5 Cities’

Bike/Walk Central Florida encourages Central Floridians to ride bikes, but we also realize that everyone may not be aware of comfortable riding routes. That’s why we’re teaming up with Healthy Central Florida on May 6 for “Bike 5 Cities,” a guided family-friendly ride-along on scenic bike trails and slow-speed residential streets. This free bike event exposes riders of all ages to paved routes and trails in Winter Park, Orlando, Casselberry, Maitland and Eatonville, allowing them to ride as far as they want and at their own pace. Ride the entire 28-mile loop or join the fun at one of four neighborhood riding sites that will offer activities for children, and snacks and refreshments for all participants. First 100 participants to register will receive a free t-shirt!

Aid stations will be located along the route, and Ride Ambassadors will provide assistance while acting as escorts. Bike helmets are mandatory.

The 28-mile Bike 5 Cities ride is FULL! Don’t worry – you can still be a part of Bike 5 Cities at any of our individual city events. Each free city event will feature rides along shorter segments of the same trails and roads that the 28-mile ride will cover, plus there will be food, refreshments, entertainment, and giveaways! Choose the event closest to you, or venture out to an area that you’ve been wanting to explore.

REGISTER for a City Event & Ride HERE!

Mead Botanical Garden, 1500 S. Denning Dr, Winter Park
Bike Ride Start Time: 8:00 a.m.

Bike 5 Cities 28-Mile Group Ride begins at 8:00 a.m. in Mead Garden in Winter Park and rolls through Orlando with stops to rest in Winter Park, Casselberry, Maitland and Eatonville before returning to Mead Garden for a total distance of 28 miles. Mechanical support, food and drinks provided.

Registration is FULL!
View the Bike 5 Cities 28-mile loop here.

Got kids or just prefer a shorter ride? There will be fun, family-friendly rides and events in Winter Park, Casselberry, Maitland and Eatonville. The rides are designed for all ages, children through older adults (not suitable for tricycles). Helmets are mandatory.

Choose the event and ride closest to you:


Cady Way Pool/Trailhead, 2525 Cady Way, Winter Park
Event runs from 8:00 a.m. to noon, with the Group Bike Ride starting at 9:00 a.m.

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

Register for the Bike Winter Park ride here.
View the Bike Winter Park route here.


Wirz Park, 806 Mark David Blvd, Casselberry
Event runs from 9:00 a.m. to noon, with the Group Bike Ride Start Time: 9:45 a.m.

Ride the Casselberry Greenway Trail – the route is an out-and-back so you can choose your own distance.

Register for the Bike Casselberry ride here.
View the Bike Casselberry route here.


Maitland Community Park, 1400 Mayo Ave, Maitland
Event runs from 10:00 a.m. to 12:30 p.m., with the Group Bike Ride starting at 11:00 a.m.

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

Register for the Bike Maitland ride here.
View the Bike Maitland route here.


Life Center Church, 63 E. Kennedy Blvd, Eatonville
Event runs from 9:00 a.m. to 1:00 p.m., with the Group Bike Ride starting at 11:00 a.m.

Ride around Eatonville with a police escort in one of Central Florida’s most comfortable community to ride a bicycle.

Register for the Bike Eatonville ride here.
View the Bike Eatonville route here.

Have questions? We have answers here.

View the event flyer here.


Interested in volunteering? Text or email Lisa Portelli, BWCF Board Member at 407.963.1213 or lportelli@wphf.org