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‘Bike 5 Cities’ – Frequently Asked Questions

Frequently Asked Questions


Q: What does it cost to participate?

A: Zip! It’s free, but please register so we can plan to accommodate everyone.

Q: Can I register on the day of the ride?

A: We won’t turn anyone away, but you’ll miss out on a few perks that you would get from registering beforehand (free t-shirts!). Plus it helps us to have enough refreshments for all


About Bike 5 Cities 

Q:Why is it called Bike 5 Cities, when I only see 4 family events?

A: It’s really not because we can’t count. The riders of the 28-mile route will pedal through five cities: Winter Park, Orlando, Maitland, Casselberry and Eatonville. Four of those cities will host family events and shorter rides.

Q: What are Ride Ambassadors?

A:Experienced cyclists who escort riders throughout the rides, provide assistance and have fun along the way. Laughing at their jokes is encouraged, but not required.

Q:How do I get my FREE t-shirt?

A: The first 100 people to register for the Bike 5 Cities 28-mile ride will receive a t-shirt. Pick up your shirt at the event table at the start of the ride.


Bike 5 Cities – 28-mile ride support

Q: Should I bring my own water and snacks?

A: You can, but water and refreshments will be provided at each city’s stop along the route. If you’d like to share your mother’s famous cookies, please bring enough for everyone.

Q: What if I don’t want to ride the entire 28-mile loop?

A: It’s up to you how far you ride. Route maps will be provided. We suggest riding from a specific, family-friendly site if you want to do a shorter ride. However, if you plan to do the entire 28-mile ride and bonk along the way Peloton Cyclist Club will provide a “broom wagon” to pick up riders who need assistance getting back to their car.

Q: What happens if I am injured on the route? What if I get a flat tire on the ride, or my bike malfunctions?

A: We aim for a safe ride for all. The ride is supported along the entire route by Peloton Cyclist Club and Ride Ambassadors, and we will provide assistance as fast as possible.

Mechanics will be available to offer assistance. If you get a flat or your bike has a boo boo, we’ll help you repair it. If we can’t do a quick repair, we’ll have a “broom wagon” to pick up you and your bicycle.

Q: Can I ride at my own pace?

A: Of course! The Bike 5 Cities 28-mile ride is planned at a slower, cruising speed (3 ½ hours to finish 28-miles with breaks). If you want to ride a shorter distance or take it even slower, we recommend the family-friendly rides. Maps will be available for the entire route and for the individual city routes if you prefer to go it alone. Click here for the 28-mile route map.

Q: Is the route well-marked?

A: The routes will not be marked, mainly because we don’t want to spray paint these nice bike trails. Ride Ambassadors will accompany the riders, and these are no-drop rides, meaning no one gets left behind. If you don’t have GPS, you can print the route maps from our web page. A SAG phone will ring to our mechanic if you need support during the 28-mile loop.


About Bike Winter Park, Bike Maitland, Bike Casselberry and Bike Eatonville

Q: Can you tell me about the events at each city?

A: Winter Park, Casselberry, Maitland and Eatonville will each host their own family-friendly, fun rides and events as part of Bike 5 Cities. The shorter bike rides will roll out after the 28-mile group ride goes through each city. The event activities and approximate distance for each unique city ride varies by location (see below).


Bike Winter Park Event & Ride

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

Event: 8:00 am – noon , Bike Ride Starts 9:00 am

Ride distance: 5.5 miles (out-and-back can be shortened)

Bike Winter Park Route Map

Winter Park activities: The city of Winter Park will have family-friendly activities for all with free refreshments, bicycle safety information and helmet giveaways.


Bike Casselberry Event & Ride

Wirz Park, 806 Mark David Blvd., Casselberry

Event: 9:00 am – noon , Bike Ride Starts: 9:45 am

Ride distance: 3.7 miles (out-and-back can be shortened)

Bike Casselberry Route Map

Casselberry activities: In conjunction with Bike 5 Cites, the city of Casselberry will host a bike rodeo with bike skills training, giveaways of bike helmets, locks and accessories, a chance to win a free bike, refreshments including free smoothies to everyone riding to the event. For more information on Casselberry specific activities, click here.


Bike Maitland Event & Ride

Maitland Community Park, 1400 Mayo Ave., Maitland

Event: 10:00 am – 12:30 pm, Bike Ride Starts: 11:00 am

Ride distance: 4.3 miles (police-escorted on neighborhood roads)

Bike Maitland Route Map

Maitland activities: The city of Maitland will host a celebration of bicycling in the community. There will be a stilt walker, DJ, face painter, unicycle juggler, and a bounce house. Tower 47 will make an appearance as well as first response vehicles the Maitland Fire Rescue Department and Maitland Police Department for a touch-a-truck event. The Maitland Police Department will host a helmet giveaway as well as Midland Fire Department will give away bicycle accessories. Food and fun will be in abundance. For more information on specific Maitland activities click here.


Bike Eatonville Event & Ride

Life Center Church, 63 E. Kennedy Blvd. Eatonville

Event: 9:00 am – 1:00 pm  Bike Ride Starts: 11:00 am

Ride distance 2.5 miles (police-escorted on neighborhood roads)

Bike Eatonville Route Map

Eatonville activities: In conjunction with Bike 5 Cites, the city of Eatonville will host “I’ll Be Right Bike” Bicycle Education & Pedestrian Safety Community Event. Activities include a Bike Rodeo, rides, food and bicycle giveaways. For more information, call 407-623-8913.



Q: Can I volunteer?

A: Absolutely! You’ll have a blast and be our new BFF! Contact Lisa Portelli at 407-963-1213 or lportelli@wphf.org

Q: What will volunteers do?

A: Volunteers are needed at the start, along the route at the city locations and at the finsh. Tasks might include handing out t-shirts, water or refreshments; helping with set-up or clean-up, showing people where to go.


The Nitty Gritty 

Q: What if it rains?

A: You’ll get wet if the rain comes after the event has started. But if the weather calls for thunderstorms, heavy rain, or raining cats and dogs, we will cancel the event.

Q: What kind of bikes are allowed on the “Bike 5 Cities” ride?

A: Any kind that can be ridden on paved surfaces. But no children’s tricycles please. Children under six or those who can’t ride a bicycle can still participate in other family-friendly activities at the individual city sites. Children bike trailers and seats are allowed.

Q: Do I have to wear a helmet?

A: Helmets are mandatory. If you don’t have and can’t afford a helmet, please contact Bike Walk Central Florida at 407-636-5606 or Barbara@bikewalkcf.org, and we’ll try to help you out.

Q: Can I bring my dog?

A: Sorry, no pets are allowed. Rover can nap or eat your shoes while you’re gone.


About the organizers

Q: Who is Bike/Walk Central Florida?

A: Bike/Walk Central Florida is a non-profit advocacy group that promotes walkable and bikeable communities through raising public awareness and advocating for safe, active transportation, and recreation. For more information, check out our home page www.bikewalkcentralflorida.org.

Q: Who is Healthy Central Florida?

A: HCF is a community-based partnership established to transform our community into the healthiest in the nation. Its aim is to get people moving more, eating healthier, feeling better and enjoying a more vibrant, energized life. For more information, check out our web site www.healthycentralflorida.org/.

Q: Who is Peloton Cyclist Club?

A: PCC is a local cycling club that provides fully supported rides for its membership. PCC also produces and supports local cycling events and multi day cycling trips throughout Florida  www.pelotoncyclistclub.com/

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