Bike 5 Cities Event


Back by Popular Demand

Bike 5 Cities is a bike ride unlike any other. What started out simply as an idea to create a bike-friendly map through the heart of five-connected urban cities and show people where they can ride comfortably, turned out to be a valuable advocacy tool in the movement to push for more bike-friendly infrastructure.

The Bike 5 Cities route map now serves as a tool to heighten awareness towards places that need safer connections, while celebrating the comfortable places to ride whether you’re only eight or pushing eighty.

The cities hosting ride pit stops along the 28-mile route pull out the welcome mat for the Bike 5 Cities riders – with greetings from local elected officials, restorative refreshments, and mini-rides for residents in and around the neighborhoods.

Last year’s inaugural ride was purposefully planned to be small and immediately maxed out at 250-plus riders.

The 2018 ride will increase its capacity in the hope of including everyone who wants to join.

Check out the 2017 event photos


WhatThe second annual Bike 5 Cities Ride is a 28-mile regional bike-ride on trails, roads with bike lanes, and slow speed residential roads for the purpose of getting people of all ages and abilities to ride at their own pace & their own way. Bike 5 Cities also offers family-friendly bike rides in Orlando, Winter Park, Maitland, Casselberry and Eatonville. See details below.

Who:  Last year, more than 250 people signed up for the ride in less than two weeks. Participants are people seeking to learn where they can comfortably ride their bikes with families and friends and looking for new places to explore.

When and where: Saturday, May 5, 2018 – Starting place is Mead Garden in Winter Park. Roll out time is 8 a.m. in the comfort of an escorted group.

Regional bike ride route:  The full route is 28-miles. Maps are also available online at http://bikewalkcentralflorida.org/2017/05/08/bike-5-cities-maps/

Register by April 30 for a Bike 5 Cities t-shirt for 28-mile loop riders. Aid stations will be located at each City, and Ride Ambassadors will escort you along the route. Bike helmets are mandatory.


28-Mile Ride Thru Five Cities 

Mead Botanical Garden, 1500 S. Denning Dr, Winter Park
Bike Ride Start Time: 8:00 a.m.  See Bike 5 Cities 28-mile loop

Saturday, May 5, 2018: Bike 5 Cities 28-Mile Group ride starts at 8:00 a.m. in Winter Park’s Mead Garden. We’ll roll through the five cities to refuel, rest and be recognized by local elected officials, friendly neighbors and fun friends in Orlando, Winter Park, Casselberry, Maitland and Eatonville – before returning to Mead Garden between 11:30 and noon. Total distance of 28 miles. Mechanical support, food and drinks provided. Recommended minimum $15 donation.

Register by April 30th for Bike 5 Cities 


Bike 1 City

For Those Who Prefer a Shorter Ride 

Got small kids or just prefer a shorter ride? There will be fun, family-friendly rides and events hosted by the cities of Orlando, Winter Park, Casselberry, Maitland and town of Eatonville. This way you can welcome the riders, enjoy refreshments while exploring the comfortable, easy bike paths around your neighborhood. Your city staff or local police will take you on mini-bike rides or share the best places to ride.

Please note these mini-rides are not suitable for tricycles or for children younger than 6. Helmets are mandatory.


 Lake Druid Park, 899 Coy Dr., Orlando

8:30 a.m. – Come and enjoy Orlando’s Lake Druid urban mountain bike park with a pump track, junior pump track and single-track trail. Elected officials and city staff will welcome the Bike 5 Cities riders at their first PIT stop event with refreshments and some mountain bike demonstrations.  Don’t forget Lake Druid Park also features a fenced dog run and community garden too. No registration necessary. 


Cady Way Pool/Trailhead, 2525 Cady Way, Winter Park

9:00 a.m. – Ride the Cady Way trail together toward Baldwin Park. The route is an out-and-back on the trail with a loop around Lake Baldwin so you can choose your own distance. Total distance 5.5 miles. See route here. Event runs from 9 a.m. to noon.

Register for the Bike Winter Park ride HERE.


Wirz Park, 806 Mark David Blvd., Casselberry

10:00 a.m. – Ride a family-friendly route partially along the Casselberry Greenway Trail and a brand new connection to Carriage Hill Drive and the back to Wirz Park via Zinnia and Wilshire. Total distance 5.9 miles. See the route here. Event from 9 a.m. – noon. More information here.

Register for the Bike Casselberry ride HERE


Maitland Community Park, 1400 Mayo Ave., Maitland

10:30 a.m. – Ride through the Dommerich neighborhood with a police escort – 5 miles total but easy to head back on your own. See route here. Event runs from 10:30 a.m. – noon. More information here.

Register for the Bike Maitland ride HERE


Eatonville Town Hall, 307 E. Kennedy Blvd., Eatonville

11:00 a.m. – Ride around the Town of Eatonville with a police escort in one of Central Florida’s most comfortable community to ride a bicycle. Route info to come. Event runs from 10 a.m. to 1 p.m.

Register for the Bike Eatonville ride HERE.


Have questions? We have answers hereInterested in volunteering? Text or email Lisa Portelli, BWCF Board Member at 407-961-9225‬ or lisa@bikewalkcf.org We need Ride Leaders to roll ahead of the group, Ride Marshalls to coach and guide the paceline and day-of-event volunteers.



Have questions, then email Barbara@bikewalkcf.org or call the BWCF office at 407-636-5606