West Orange Trail: 10-Mile Private Bike Tour Exploring Downtown Winter Garden and Oakland
5 Ratings
Winter Garden
Embark on a 10-mile private bike tour of the West Orange Trail, exploring downtown Winter Garden and Oakland. Discover the beauty of nature, charming towns, and enjoy a fun scavenger hunt along the way!
Duration: 3 hours
Cancellation: 1 day learn more
  • Winter Garden Heritage Museum - Passing by this historical museum, where you will find a scavenger hunt trail clue and perform a trail task nearby.
  • Downtown Winter Garden - We’ll pass through the historical downtown of Winter Garden.
  • West Orange Trail - Stopping by the Butterfly Garden, where you will find several scavenger hunt trail clues and perform a trail task.
  • 747 Machete Trail - We’ll stop by this amazing nature preserve, answering some scavenger hunt trail clues and performing a trail task (pic) of a specific feature.
  • West Orange Trail Bikes and Blades - This is Killarney Station, where we will turnaround and head back to our starting point, Winter Garden Station.
  • West Orange Trail - Stopping at this feature of the trail to review and answer a scavenger hunt trail clue and perform a trail task (selfie) at this location.
  • Oakland - We’ll pass through the downtown area of the Town of Oakland, answering several scavenger hunt trail clues.
What's Included
  • Bottled Water
  • Complimentary use of Bike Phone Mount
  • Interactive Scavenger Hunt (for mobile)
What's Not Included
  • Bicycle (bring your own OR rent bike $10/hr from WheelWorks)
  • Helmet (bring your own)
  • Refillable Water Bottle (bring your own)
Additional Information

We cordially invite you to join us for a 10-mile bicycle tour of the West Orange Trail (WOT), where you’ll have the opportunity to experience its natural splendor and significance to the local populace. This trip enables you to see the enchanting downtown areas of Winter Garden and Oakland, enjoy diverse natural wonders such as the Butterfly Garden and Oakland Nature Preserve, and appreciate the refreshing shade offered by copious trees along the route. A thrilling, interactive scavenger hunt (compatible with mobile devices) will be a part of the tour. Remember to bring your mobile device, a cycling helmet, and a refillable water container. You can bring your own bicycle(s) or rent some at our assembly point. The West Orange Trail eagerly awaits your visit!

455 E Plant St
East Plant Street
Meet at Winter Garden Station. Bring your own bike or rent bike from WheelWorks. Look for me, Chris—your tour guide, at the stairs, parking lot side of station. Up to 4 complimentary phone mounts provided for use. A waiver for each participant must be signed before tour begins.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(5 Ratings)
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Dec 28, 2023
Pedaling in the Florida Sunshine - I really enjoyed the guided tour and scavenger hunt Chris led. We explored downtown Winter Garden and historic Oakland, too. Pedaling in the shady bike path was fun, as was looking for scavenger hunt answers and learning about Florida’s history. Chris provides the phone mounts, and bikes can be easily rented at Winter Garden Station if needed. This is a nice expedition, especially if you are visiting the area and want to see the “real” Florida.
Review provided by Viator
Dec 27, 2023
Pedal your way through Florida’s history! - If you are interested in seeing some of the “real” Florida, I highly recommend you take this bike tour/scavenger hunt with Chris in historic Winter Garden on the West Orange Trail. Relax and enjoy learning about bass fishing tournaments and the citrus industry as you pedal along this tree canopied trail. Chris is a friendly and knowledgeable guide, and if you’re lucky, you’ll see a peacock or two as well, like we did!
Review provided by Tripadvisor
Dec 27, 2023
West Orange Trail from a new perspective - This was a fun interactive bike tour of the West Orange Trail suitable for all ages-- and is perfect for the leisurely rider as myself! It's a private booking, so you maintain your own comfortable pace for your group. Expect to spend about 2.5 hours if you take your time to enjoy the nature as we did. The trail is flat, wide, and shaded with a gorgeous canopy of trees. I love the vibrant atmosphere sharing the trail with other cyclists, walkers, and runners. There's plenty of photo/ selfie opportunities and stops along the way. I went with a group of friends. We brought our own bikes, but you can also rent them at the meeting station. Chris is a great tour guide and an avid cyclist herself. At the beginning of the tour, she provides each cyclist with a bike phone mount for the scavenger hunt, and water. I'd suggest getting to the meeting point about 15 min ahead of the start time so she can fit the phone mount to your bike. She also offered a small snack and electrolytes for our water, but it was a cool day during our tour, so we didn't need that extra electrolyte boost. Even though we are already frequent users of the WOT, Chris's tour offered fun trivia about the town and points of interest along the trail that we've never noticed or overlooked before. The scavenger hunt had us exploring the trail from a fresh perspective. Highly recommend this bike tour, whether you're a first time visitor, or a resident of the area alike! Get out and enjoy nature!
Review provided by Tripadvisor
Dec 27, 2023
Ride and Seek. Discover and enjoy! - Chris was very nice and knowledgeable. Thought I knew the trail but saw things I had not seen b4. Fun activity! Try it out!
Review provided by Tripadvisor
Dec 7, 2023
West Orange Trail scavenger hunt bike tour - A great bike tour of the West Orange Trail! My tour guide Chris was personable and welcoming and the mobile scavenger hunt was great fun! The trail itself was beautiful, along with the weather! Chris was very accomodating by providing water and even a phone holder! Great experience
Review provided by Viator
Select Date and Tickets
up to 4 guests
1 Adult
July 2024