Updated March 2018
Stretching from Winter Garden to Apopka, the West Orange Trail is a 22-mile long paved rail-trail. Bike, walk, run or skate your way through this itinerary to discover some of the best sights, sips, and bites along the trail.
START: Killarney Station/West Orange Trail Bikes & Blades
Located 20 minutes from Orlando, Killarney Station is the best place to begin your biking adventure. Besides serving as a trailhead for the beginning of the West Orange Trail, Killarney Station is one of only two stations offering bike rentals.
After parking your car, head inside to pick up your wheels from West Orange Trail Bikes and Blades. (Or bring your own!) Bike rentals are $7/hour or $30/day for comfort bikes and $11/hour or $50/day for road bikes. Make sure to bring a bike lock, as they are not provided. The rental shop is open from 9am-5pm on weekdays, and 7:30am-5pm on weekends.
Once you’ve picked up your bikes, head left on the paved trail towards Winter Garden. If you accidentally go in the wrong direction, you’ll see a sign alerting you that you’re about to leave the West Orange Trail.
As you coast along the 14-foot wide trail dotted with greenery and oak trees, your first point of interest, which doubles as a prime photo spot, will be the restored railroad bridge.
STOP 1: Oakland Nature Preserve
Continue riding until you reach the Oakland Nature Preserve on your left. There’s a covered station where you can lock up your bikes and enter the park, which is open year-round and free to the public.
Inside, you’ll find six well-marked hiking trails (all under 1-mile each), a 0.6-mile long boardwalk (wheelchair accessible), and an education center with a museum, restrooms, brochures/maps, a turtle exhibit, and more. The 128-acre park includes diverse ecosystems including uplands and forest wetlands.
The boardwalk is the main draw of the park, weaving through three unique ecosystems before delivering you to the scenic shores of Lake Apopka. If you’re lucky, you may spot alligators and other wildlife along the way.
STOP 2: Town of Oakland
Passing through the tiny town of Oakland, once a bustling railroad community established in the 1800s, is one of the most peaceful stretches of the trail. Thanks to the signs alerting you that you’ve entered a quiet zone, you’ll hear little else than birds chirping and leaves rustling in the wind. You’ll know you’ve arrived in the center of town when you reach a small roundabout on the trail.
If you feel like stretching your legs, park your bikes and take a stroll around the historic Town Hall, bubbling fountain, and picturesque water tower. There are also several benches for stopping to share a snack.
STOP 3: Oakland Park
Love having picnics in the park? Then pack some goodies to share and make a stop at Oakland Park. Huge oak trees dot the shore of a small lake where you’ll find a picnic table for hosting your feast. There’s a bike rack if you’d like to lock up your bikes and stay awhile.
STOP 4: Butterfly Garden at Tildenville Outpost
One of my favorite aspects of the West Orange Trail is its natural beauty. The old oak trees, wildlife, flowers, and scenic stopping points are a welcome respite from the city. If you aren’t paying attention, you can easily pass right by one such scenic stopping point: the tiny butterfly garden off the trail to your right. While it’s hidden in plain sight, the garden still has a subtle secret garden feel.
Part of the Tildenville Outpost, the garden is small but packed with unique flowers. Wander through slowly and see how many butterflies you can spot during your visit.
You won’t find any bike racks here, but the garden is so small you won’t need one.
STOP 5: Plant Street Market/Downtown Winter Garden
My favorite West Orange Trail date is a 4.5-mile bike ride followed by a pizza from Michael’s Ali Coal-Fired Pizza and beer from Crooked Can Brewery at Plant Street Market. The trail leads you straight to the market where there are multiple bike racks, a huge outdoor patio, and about a dozen food and artisan vendors selling everything from BBQ to cold pressed juice and made to order donuts. Did I mention there’s also a craft brewery?
True, pizza and beer will cancel out any calories you’ve burned, but it’s totally worth it. After working up an appetite cruising along the trail, Plant Street Market is an ideal place to refuel. My boyfriend and I typically spend a few leisurely hours here, especially if the weather is nice. Just make sure you give yourself ample time to ride back and return your bikes before the rental shop closes down for the day.
While you’re here, it’s also worth taking a stroll through downtown Winter Garden. Stop for a coffee at Axum Coffee, conduct a mini pub crawl, or just take in the local sights. You can even join a food tour with Winter Garden Food Tours on select days. The center of town is just several minutes from Plant Street Market on foot.
Here are a few activities to check out during your visit:
- Bartender Basics at Market to Table: Wednesdays and Thursdays at 5pm (sit at the bar for cocktails and learn to make some new drinks! Stop in or call ahead for reservations (407) 395-9871)
- Flip Flop Lunch food tour: Thursdays and Fridays at 11:30am
- Fridays on the Plaza: live music from 7-9pm
- Winter Garden Farmers Market: Saturdays from 9am-2pm
- Live music at Crooked Can: Saturdays and Sundays from 1-4pm
- Brunch and Brewery food tour: Sundays at 11am and 2pm
STOP 6: Central Florida Railroad Museum
If you decide to walk through Winter Garden, it’s worth stopping into the Central Florida Railroad Museum. Sections of the West Orange Trail were once a railway, so visiting the museum will help you better understand the history of railroads in the area. Opt for a guided tour from one of the volunteers for the best experience.
The museum is open daily from 1-5pm. Entry is free, although there is a donation box if you’d like to contribute.
KNOW BEFORE YOU GO
There are multiple service stations located between Killarney Station (start point) and Plant Street Market (end point) where you can use the restroom, get a drink of water, or just take a breather.
Biking at a leisurely pace directly from West Orange Bikes & Blades to Plant Street Market (4.5 miles) will take about 45 minutes. Factor in more time if you plan on stopping anywhere along the way.
The West Orange Trail is open from sunrise to sunset. If you’re renting bikes for the day, make sure you return before 5pm when the rental shop closes.
West Orange Trail Bikes and Blades
Winter Garden, FL
About the Author/Photographer:
Stephanie Patterson is the managing editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at www.spattersonphotography.com and www.traveltasteclick.com.
All images by Stephanie Patterson unless otherwise noted