Bike 5 Cities to ride through Maitland and Winter Park

The Bike 5 Cities event will have hundreds of cyclists riding 28 miles across five cities.

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  • | 9:44 p.m. April 24, 2019
  • Winter Park - Maitland Observer
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Winter Park resident Lisa Portelli has always been an avid bicyclist. Even at a young age, she would bike as far as 28 miles or more.

On her many bike rides, Portelli — a self-described bike commuter, road cyclist and  triathlete who lives on a bike — has seen the many back roads, trails and secret nooks and crannies that fill up the Central Florida region and the many cities within.

Three years ago, Portelli decided others in the Central Florida area should be encouraged to cycle and see the same sights that she has.

“People always ask me, ‘Where do you ride?’” Portelli said. “We need to show people there are bike-friendly roads and trails in this community and show where they are.”

On Saturday, May 4, hundreds of bikers will gather at Mead Botanical Garden in Winter Park for the start of the third annual Bike 5 Cities event put together by Bike/Walk Central Florida. The event will have bicyclists starting in Winter Park and traveling to Orlando, Casselberry, Maitland and Eatonville before returning to Winter Park. 

“It’s for riders of all ability levels,” said Katie Clarke, event manager for Bike 5 Cities. “If you’re less comfortable, jump on for the group ride, there will be experienced cyclists in the group. Twenty-eight miles on a bike is not as long as it (sounds), especially if you’re stopping and taking water breaks and getting snacks and getting on the road again. 

Take A Ride

Bike 5 Cities can serve as a leisurely ride through many of Central Florida’s cities — but the staff at Bike/Walk Central Florida hope it can be a wake-up call to the many ways to get around the area, as well. 

“It was initially launched because Bike/Walk Central Florida wants to encourage people to get out on their bikes,” Clarke said. “We want them to ride not just for recreation but for transportation purposes. Maybe when you’re going to dinner or running an errand. We realized there was need for people to know what routes to take so they wouldn’t have to take high-speed roads. It’s a fun bike ride, but it’s also to raise awareness. Cities are fully invested, which we love.”

Portelli, Bike/Walk Central Florida’s co-founder, recalls sitting down three years ago, taking out a map of the Central Florida area and drawing a route between the five cities. She said the important thing for her in the moment was to find a route that could link between the five municipalities on bike-friendly roads. The surprising thing was that she finished designing the route in an hour. 

“I sat down, and it was in my head,” Portelli said. “I thought, ‘I know I can do this,’ and started at Mead Garden, because I knew the Orlando Urban trail and the Cady Way trail, and I knew where the Casselberry connectors were. I know the roads that I ride on … I put it all together, and there it was.”

The starting point at Mead Botanical Garden will have between 200 and 250 riders, with the rest being able to leave from starting points at their own cities in case they want to bike faster or at a more relaxed pace, Clarke said. Those multiple starting points also allow for more riders to join the event. The first registered riders at Mead Botanical Garden receive a free T-shirt.

Each city sets up its own rest stop with water and healthy snacks. City mayors have issued declarations from the rest stops in years past, Clarke said. The organization has had conference calls with representatives from each city’s local government.

Maitland Parks and Recreation Director Jay Conn said Bike/Walk Central Florida supplies much of the fruit and refreshments; his staff merely sets up the station for arriving bicyclists.

“We have water and snacks for the riders,” Conn said. “We have a Parks staffer at the table there as the riders come through. … The (cyclists) are riding together, and four of them signed up to leave from Maitland.”

The first year started with 50 or 60 riders signing up beforehand but eventually grew to 200 riders. The second year had about 300 riders. Staff expects this year to have around 300 riders, as well, but hopes to see the number grow even higher by May 4.

“Get a helmet and go to a trail — that’s my first advice,” Portelli said. “You still have to watch the crossings, but I really steer people toward our network of trails.”

Helmets are required for the Bike 5 Cities event. 


If You Go: Bike/Walk Central Florida’s Third Annual Bike 5 Cities

WHEN: Starts 8 a.m. 

Saturday, May 4

WHERE: Mead Botanical 

Garden, 1300 S Denning Drive, Winter Park

COST: Minimum $15 donation. Registration deadline is April 30. Helmets are mandatory, and aid stations will be provided.


CONTACT: (407) 636-5606



Winter Park





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