Eat, Drink and Explore the West Orange Trail

by Stephanie Patterson

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.

West Orange Trail Date Itinerary #1

START: Killarney Station/West Orange Trail Bikes & Blades

Location: 17914 FL-438, Winter Garden, FL 34787

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. Parking is free here and there are public restrooms.

After parking your car, head inside to pick up your wheels from West Orange Trail Bikes and Blades. Or bring your own, of course. Bike rentals start at $11/hour or $45/day, with options for comfort bikes, road bikes and e-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. This iconic steel-truss trestle allows bikers to safely cross over the turnpike.

STOP 1: Oakland Nature Preserve

Location: 747 Machete Trail, Oakland, FL 34760

Continue riding to reach the Oakland Nature Preserve on your left side. 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, snakes, bobcats, birds and other wildlife along the way.

Oakland Nature Preserve is a hidden gem so expect to make this a re-occurring date destination for future visits.

Oakland Nature Preserve located along the West Orange Trail — Oakland Nature Preserve at sunset. Image credit: Oakland Nature Preserve

STOP 2: Town of Oakland

Location: 220 N. Tubb St., Oakland, FL 34760

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: The Healthy West Orange Arts & Heritage Center

Location: 126 Petris Avenue, Oakland, FL 34760

The Healthy West Orange Arts & Heritage Center is a delightful stop where you can browse rotating art and history exhibits, explore Oakland's rich heritage, join wellness and cultural programs, stroll through the herb garden, and relax along the West Orange Trail with an ice cream or snack from the on-site Oakland General concession. This is your chance to snag a smidge of air conditioning while exploring the West Orange Trail.

STOP 4: Speer Park

Location: 331 N. Tubb St., Oakland, FL 34760

It's worth venturing just off the Trail to stop at Speer Park, where towering oak trees, a charming gazebo, pickleball courts, and plenty of green space create the perfect spot to relax or enjoy a picnic. Keep your eyes peeled while you're there as you'll likely spot one of Oakland's famous wild peacocks strutting through the park, adding a colorful touch to an already picture-perfect visit.

If you prefer not to venture off, know that there are plenty of locales along the trail that make for sweet picnic spots. As you continue riding from Oakland to Winter Garden, you'll pass another Trailside Pavilion on the West Orange Trail.

STOP 5: Butterfly Garden at Tildenville Outpost

Location: 1064 Tildenville School Rd., Winter Garden, FL 34787

One of the best 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. It's a short romantic stroll to keep your heart aflutter with your date!

You won’t find any bike racks here, but the garden is so small you won’t need one.

STOP 6: Plant Street Market & Downtown Winter Garden

Location: 426 W. Plant St., Winter Garden, FL 34787

As you enter Historic Winter Garden, there are tons of places to stop along Plant Street. Definitely spend some time at Plant Street Market, which is anchored by Crooked Can Brewery. 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. So yeah, after working up an appetite cruising along the trail, Plant Street Market is an ideal place to refuel.

Fun fact: Beer has actually been praised as a decent post-exercise recovery drink! Cheers to that.

Plant Street Market Winter Garden — Plant Street Market | Image credit: Stephanie Patterson

While you’re here, it’s also worth taking a stroll through Downtown Winter Garden. Stop for a coffee at Axum Coffee or an espresso at Rosallie, conduct a mini pub crawl, or just take in the local sights. 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:

Fridays on the Plaza: live music from 7 p.m.-9 p.m.
Winter Garden Farmers Market: Saturdays from 8 a.m.-1 p.m.
Live music at Crooked Can: Select weekends outdoors

STOP 7: Central Florida Railroad Museum

Location: 101 S. Boyd St., Winter Garden, FL 34787

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. Museum entry is free, although there is a donation box if you’d like to contribute.

***That seven-stop itinerary will properly be more than enough. However, the West Orange Trail is lengthy and you could do much more.***

West Orange Trail Date Itinerary #2

START: Winter Garden Station / Winter Garden Trail Park

Location: 455 East Plant St., Winter Garden, FL 34787

Once you've mastered the Killarney Station to Plant Street Market route, try a new one! If you need to rent wheels, begin at Winter Garden Station where you can rent comfort bikes from Winter Garden Wheel Works. As you continue on the West Orange Trail, you'll pass the Winter Garden Library, followed by a downhill section where you may just pick up an unexpected speed while biking.

STOP 1: Chapin Station

Location: 501 Crown Point Cross Rd., Winter Garden, FL 34787

Take a pit-stop at Chapin Station. This trail outpost and park in one features two awesome playgrounds, a paved walkway through a peaceful garden, and restroom facilities. After departing Chapin Station, the following stretch of the West Orange Trail is truly peaceful, with much less hustle-and-bustle and more more shade coverage.

STOP 2: Wood Bridge on West Orange Trail

Location: 1688 E Crown Point Rd, Ocoee, FL 34761

Whether you physically stop or not, do take note of the charm of this bridge crossing. After gliding for a while on the smooth pavement, the gentle bumps of the wood bridge is a nice change of pace.

STOP 3: The Backyard & Downtown Ocoee

Location: 2214 West Rd., Ocoee, FL 34761

Take a break from the trail to discover Ocoee's growing local scene. Just a short ride from the West Orange Trail, you'll find The Backyard, a lively outdoor gathering spot where food trucks, lawn games, live entertainment, and a self-pour beverage wall create the perfect place to refuel after a ride.

After departing here, you'll pass Orlando Memorial Garden.

STOP 4: Chua Bao An Buddhist Temple

Location: 5788 N Apopka Vineland Rd., Orlando, FL 32818

For an unexpected sight, marvel at the Chua Bao An Buddhist Temple, located near the Apopka Vineland Outpost. This structure makes for a peaceful pause amongst gorgeous gardens and statues.

Find the Chua Bao An Buddhist Temple along the West Orange Trail at Apopka Vineland Station.

STOP 5: Clarcona Horse Park

Location: 3535 Damon Rd., Apopka, FL 32703

As you're exploring the northern end of the West Orange Trail, don't miss the spur leading to Clarcona Horse Park. This unique trail stop is the only equestrian outpost along the West Orange Trail, where you'll find horse arenas, shaded picnic areas, parking, restrooms, and even RV and tent camping for equestrian visitors.

A parallel equestrian trail also runs alongside portions of the paved path, so it's not unusual to spot horseback riders sharing the scenic corridor, a fun reminder that this trail isn't just for bikes and walkers.

Most couples will probably end exploration here. Otherwise, Apopka Station is about another 13 miles.

KNOW BEFORE YOU GO

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

Location: 17914 FL-438, Winter Garden, FL
Phone number: (407) 877-0600

Hours:
Monday-Friday: 9 a.m.-5 p.m.
Saturday-Sunday: 7:30 a.m.-5 p.m.
www.orlandobikerental.com

Winter Garden Wheel Works

Location: 455 East Plant St., Winter Garden, FL 34787
Phone number: (407) 877-7433

Hours:
Tuesday – Sunday: 10 a.m.-5 p.m.
www.wgwheelworks.com

TRAIL MAP

Florida food and travel photographer and writer Stephanie Patterson

About the Author/Photographer:
Stephanie Patterson is 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.

Updated by Nancy DeVault (June 2026)