Bike 5 Cities
Bike 5 Cities — 30-Mile Ride
Our signature experience. Five cities. One ride. All levels welcome.
Why Ride?
The 30-mile Bike 5 Cities ride is Central Florida’s friendliest group ride for people of all experience levels. Whether you’re riding to push your distance, soak up the scenery, or enjoy a social, supported group ride — this route is designed to take you through trails, safe neighborhood streets, and city connections that showcase what a bike-friendly region looks like.
Choose a guided pace group or ride solo — either way, you’ll experience five welcoming host cities and see how connected our communities really are by bike.
Quick Facts
Start Locations (Choose your starting city when you register. Each city also serves as a rest stop with water, light snacks, and restrooms along the way)
- Orlando – Colonialtown Neighborhood Center
- Winter Park – Mead Garden
- Eatonville – Denton Johnson Community Center
- Maitland – Maitland Community Park
- Casselberry – Wirz Park
Time
- Check-In: 7:00 AM
- Rides departs starting at 7:30 AM
Ride Length
- 30 miles (final route announced in late summer)
- Allow 3-5 hours, depending on your pace and number of stops
Ride Types
- Guided Group Ride
- Join a group led by Ride Leaders and Sweeps — no one gets left behind. You’ll ride with folks at a similar pace and stop in each host city along the way. Just choose your pace when you register:
- Fast Pace: Regularly ride 30+ miles? Comfortable at 15+ mph? This fast-paced group is for you. Expect minimal stops.
- Moderate Pace: You’ve ridden this distance before and want a steady challenge. Expect a balance of a moderate pace with rest breaks along the way
- Leisurely Pace: 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.
- Join a group led by Ride Leaders and Sweeps — no one gets left behind. You’ll ride with folks at a similar pace and stop in each host city along the way. Just choose your pace when you register:
- Self-Guided
- Prefer to skip the group and ride at your own pace? The self-guided option gives you flexibility to start anytime between 7:30–9:00 am. You’ll still enjoy the same route and rest stops — just on your terms.
- Follow the Ride with GPS app with turn-by-turn directions
- Printed cue sheets and route signs available
- Bright arrows and wayfinding signs on the route to keep you on track
- Prefer to skip the group and ride at your own pace? The self-guided option gives you flexibility to start anytime between 7:30–9:00 am. You’ll still enjoy the same route and rest stops — just on your terms.
Need a Bike?
Bike rentals are available at Mead Garden through our partners at Unlimited Biking. Rentals must be booked separately from your event registration — and you’ll need to select Winter Park (Mead Garden) as your start location during registration to access your rental on ride day.
Ready to Ride?
Spots fill quickly — especially for guided groups!