30-mile “Bike 5 Cities”

Our signature ride! Go self-guided at your own pace or join a guided group (fast, moderate, or leisurely pace).

⏱Takes about 3–5 hours depending on your pace and breaks
🔁 Loop ride — starts and ends at the same location. Final route to be shared late summer.

• Choose your starting locations:
  • Orlando - Colonialtown Neighborhood Center
  • Winter Park - Mead Botanical Garden
  • Eatonville - Denton Johnson Community Center
  • Maitland - Maitland Community Park
  • Casselberry - Wirz Park
• Select your Ride Type:
  • Self-guided: Want the freedom to set your own pace, take breaks when you choose, and explore the route on your terms? Use Ride with GPS for turn-by-turn navigation, follow the bright arrows and signage to keep you on track, and stop at any host city for water, snacks, and restrooms.
  • Fast Pace Group: Regularly ride 30+ miles and comfortable cruising at 15+ mph? This fast-paced group is for you. Expect minimal stops.
  • Moderate Pace Group: Ridden this distance before and want a steady challenge? This group balances a moderate pace with rest breaks along the way.
  • Leisurely Pace Group: New to 30 miles or just in it for a chill ride? You’re in the right place. Relaxed pace with plenty of rest stops.

10-mile “Bike 5 Main Streets”

A relaxed guided group ride through Orlando’s Main Street Districts using the trails, baths, and bike lanes of the Orlando Urban Trail, Livingston St, Maguire Blvd, Bumby Ave, and Corinne Drive's pop-up bike lane. Perfect for newer urban cyclists. Choose to start at Winter Park or Orlando for this chill 10-mile ride.

⏱About 2 hours with 2 short stops
🔁 Loop ride — starts and ends at the same location. Final route to be shared late summer.

• Choose your starting location:
  • Orlando - Colonialtown Neighborhood Center
  • Winter Park - Mead Botanical Garden
• Ride Type:
  • Leisurely guided group ride

Bike 5 Cities is a 30-mile regional bike-ride that advances equity through better transportation options; improves safety by teaching people of all abilities and ages how to use routes safely; enhances local economies by bringing bike “traffic” to businesses; and builds public support for connecting bike routes throughout Central Florida.

The newly named, BIKE 5 event is unique and offers several ride options this year! For the original Bike 5 Cities, 30-mile ride you can choose to ride in a Guided Group ride or the Self-guided, ride on your own option. Each Guided Group will have an experienced ride leader and a sweep in the back. These Guided groups will leave in waves (A, B, or C) based on participants chosen level/speed. For the Self-guided, ride on your own option, you may start in any of the 5 host city locations any time between 7:30-9:00am. This option is for those who want to participate and prefer avoiding riding in any size group. It’s also good for riders who want a faster pace or just prefer start, stop, and rest time flexibility.

Not quite ready for a 30-mile adventure? Each year, we have some shorter distance options. This year we’ve added a 10-mile ride, Bike 5 Main Streets. Come experience the joys of riding a bike!

Every step, pedal, and roll counts toward saving lives. By sponsoring Bike/Walk Central Florida, you are directly supporting programs and initiatives that make our streets safer for everyone—children walking to school, families enjoying a bike ride, and individuals navigating their communities with confidence. Your sponsorship fuels critical work that saves lives, empowers communities, and creates safer, active, and more connected neighborhoods.

When you partner with Bike/Walk Central Florida, your brand becomes a visible champion of our mission, connecting with thousands of community members while aligning with a purpose that resonates: ensuring everyone has the right to move safely.

Learn More About Sponsorship!Become a BIKE 5 Sponsor!

Want to volunteer?

BIKE 5 will need plenty of volunteers leading up to and during the event! We need people to help organize registration materials, help mark the course, put up signage, event day check in, pass out shirts to riders, help direct riders to their group, let folks know where to start, or to be ride leaders or sweeps.

Be a ride leader!

Are you an experienced cyclist familiar with riding on Central Florida roads? Do you enjoy sharing your love of bicycling with others? Bike 5 needs you to help guide riders along the route for a worry-free ride. As a Ride Leader, you will help riders in the group maintain a safe and enjoyable pace.

Each Guided group will be accompanied by a volunteer Ride Leader and Sweep (that could be you!). Ride Leaders will preview the course with before October 1st to ensure they are familiar with the course. We are looking for support for all of our BIKE 5 rides (30-mile, 10-mile, various paces).

For volunteer inquiries, please contact us at Bike5Cities@bikewalkcf.org

Need a bike?

Bike rentals are available at Mead Garden through Unlimited Biking. Rentals must be booked separately from event registration. Be sure to select Winter Park / Mead Garden as your start location if you plan to rent a bike!

Reserve your bike here »