Experience the West Orange Trail Like A Local
Your Local Guide to the West Orange Trail in Winter Garden, Oakland, Ocoee, and Apopka, Florida
Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty
The West Orange Trail has gained popularity over the years with both visitors and local trail enthusiasts, and most people in Central Florida have heard of it, but knowing of a trail and really knowing the trail are two very different things. This local guide to the West Orange Trail in Winter Garden, Oakland, Ocoee, and Apopka highlights hidden gems, food stops, and can’t-miss experiences along one of Central Florida’s most popular trails. If you're not familiar, here's a quick overview:
Quick Facts about the West Orange Trail
- The West Orange Trail is located in Orange County, Florida, west of Orlando.
- The West Orange Trail is 22.32 miles long and runs from Oakland, Winter Garden, Ocoee, and ends in Apopka.
- The trail surface is paved and 14 feet wide.
- The West Orange Trail is a multi-use trail and permits bicycles, mobility devices, pedestrians, skates, skateboards, horses, and electric bikes (some restrictions apply).
- There are 10 stations and outposts along the length of The West Orange trail, which include amenities like restrooms, picnic tables, parking, playgrounds, and more.
- The trail is open daily from sunrise to sunset.
- Leashed pets are permitted.
9 Top Stops On the West Orange Trail
1 | Oakland Nature Preserve (Oakland, Florida)
A hamlet of a downtown, and as its name alludes to the many towering Oaks, Oakland is a true trail town with the West Orange Trail being a focal point running directly through its town center. Home to our 1st hidden gem: The Oakland Nature Preserve. This 128-acre preserve features 3.5 miles of nature trails, including an exercise loop and a bird blind. A boardwalk leads visitors above wetlands that lead to Lake Apopka. A covered pavilion provides a shaded stop to enjoy views of the water before heading back. There is no fee to enter, but donations are accepted.
>> Pro Tip: Don't miss the Oakland Nature Preserve events. They offer tours, kids' activities, birding walks, and so much more. Right now, Firefly Nights is happening on select dates in March and April, where the preserve stays open later in the evening to explore the boardwalk to find fireflies.
2 | Oakland Arts & Heritage Center (Oakland, Florida)
The 2nd hidden gem on our guide is the Healthy West Orange Arts & Heritage Center in the Town of Oakland. Located in the heart of downtown, the center is known for celebrating local art and for its Annual Heritage Day event held in January. Don't miss grabbing a scoop of ice cream or a hot dog at Oakley's Trailside Treats. Be sure to head to the Farmers Market held on the 2nd & 4th Thursday of the month from 9am - 2pm. You'll find everything from produce to locally made food and handicrafts.
>> Pro Tip: Locals know to head to Yoga on the Porch at the Center on Mondays at 6:30pm. (You don't need a reservation, and while there is no set fee, donations are accepted.)
3 | Butterfly Garden at Tildenville Outpost (Winter Garden, Florida)
Another hidden gem along the West Orange Trail is our #3 spot to add to your must-visit list. The Tildenville School Road Outpost is home to the Butterfly Garden. Explore the garden, a pollinator habitat created with native plants to attract butterflies, hummingbirds, and bees. While keeping your eye out for butterflies, you'll see some cheeky artwork pop up, including painted rocks and fairy houses.
>> Pro Tip: There is public parking available next to the Garden, so even if you're not coming from the trail, you have an easy place to stop and enjoy the garden.
4 | Plant Street Market (Winter Garden, Florida)
Local favorite #4 Spot, located in downtown Winter Garden, Plant Street Market is one of the most popular food stops along the West Orange Trail to get some food and refreshments. Here, you'll find several food and drink stalls, including the new Jam Hot Chicken, known for its bold "Jam" heat level. Outside patio seating is perfect to grab a local brew at Crooked Can Brewing, and for a tasty snack, check out Nosh Popcorn or Sir Benji's Donuts for a sweet treat. You really can't go wrong with any of the stalls here, so feel free to mix and match for sharing.
>> Pro Tip: If you try out Jam Hot Chicken (and we recommend you do), heed this advice: If you're a typical mild-to-medium wing heat level when you go out for wings, start with the mild (and thank us later). For those brave souls with mouths of steel, have at the "Jam" hot level; just be sure to get a cold beverage to wash it down.
5 | Rosallie Le French Cafe (Winter Garden, Florida)
Stop #5 is a well-deserved sweet treat after a day on the trail. If drooling over a display of flaky croissants, fruity glazed tarts, and fluffy quiche feels is what you call a perfect Sunday morning, then Rosallie Cafe may be for you. Don't let the display case cloud your judgment because their full menu of brunch all-day delights, lunch bites, and coffees are not to be missed. Located on Plant Street, near the Centennial Plaza, this local favorite has an outdoor patio and indoor seating.
>> Pro Tip: Take your goodies to go, then head over to Centennial Plaza and grab a bench or a swing next to the fountain for the best small town vibes while you enjoy your treat.
6 | Central Florida Railroad Museum (Winter Garden, Florida)
All aboard on stop #6 at the Central Florida Railroad Museum in downtown Winter Garden. Located on S. Boyd Street between W Joiner & Tremaine Street, this museum is only 1 block from the West Orange Trail. Explore exhibits with train artifacts, including maps, signage, and more. Currently on display is a large collection of dining car china, including pieces from multiple railroads across the country, such as the Florida East Coast Railway & Atlantic Coast Line Railroad, dating back to the 1920s.
>> Pro Tip: The Railroad Museum is closed on Sundays and Mondays, so plan accordingly. Also, the museum has free admission (donations are appreciated).
7 | The Backyard (Ocoee, Florida)
Heading north into Ocoee is The Backyard, an outdoor dining experience that is located just off the West Orange Trail and West Road, just west of the 429. Multiple food vendors have come together to offer delicious foods ranging from pizza and tacos to barbecue, sushi, and more! In addition to the food options, the self-pour taps feature 24 options, including beer, wine, and more, with some local selections. With a covered patio and outdoor seating, fire pits, and yard games, there are plenty of reasons to stick around and hang out.
>> Pro Tip: Order ahead online to have your food ready for you when you arrive off the trail and don't miss the hosted events, including live music.
8 | The Nauti Lobstah (Apopka, Florida)
History and good food collide in our #8 gem located in downtown Apopka. The Nauti Lobstah, right off the West Orange Trail at S. Forest Avenue & W. Orange Blossom Trail, is housed in the historic train depot from the late 1920s, which was used to transport oil barrels. Part of the charm of this restaurant is catching a glimpse of the toy train set that runs along the main dining room. Known for their large selection of tasty seafood, including the lobster rolls (our personal favorite), and the famous 2-foot lobster roll, complete with 2lbs of Maine lobster, is not to be missed!
>> Pro Tip: Don't miss walking around the restaurant. This original structure has plenty of history to explore throughout.
9 | Kit Land Nelson Park (Apopka, Florida)
Last, but certainly not least, is the Kit Land Nelson Park. Located near the Nauti Lobstah at E. 1st Street and N Park Ave, this park is a great place to relax at the north end of the trail. This 5-acre park features a central gazebo, shaded picnic areas, a splash pad (to cool off after a long bike ride), playground, and racquetball courts. Next to the park is the Apopka Station, the northern-most station along the West Orange Trail, which offers parking, a playground, and restrooms.
>> Pro Tip: Check the City of Apopka's website for updates and seasonal hours of operation for the Splash Pad.
Looking to Live Along the West Orange Trail?
Living near the West Orange Trail means having coffee shops, local events, and miles of outdoor space woven into everyday life.
For those who crave being on the trail and living in one of the trail towns in west Orange County, working with a local expert to find the right location for your family's needs is important. Jeffrey Funk, Team Leader of The Funk Collection team, is a local Southwest Orlando resident of over 25 years. Having lived in the area and being a biker himself, understands the love of the trail.
Curious what it looks like to live near the West Orange Trail or which communities might be the right fit?
Connect with The Funk Collection team, your Southwest Orlando experts, to start your home search today. Connect at 407-930-9829.
Looking for more insight on neighborhoods near the trail? Explore our guide to communities along the West Orange Trail.
West Orange Trail FAQs
How long is the West Orange Trail?
The West Orange Trail is approximately 22 miles long and connects Oakland, Winter Garden, Ocoee, and Apopka in Central Florida.
Where can parking be found along the West Orange Trail?
Parking is available at multiple trailheads and outposts, including Oakland, Winter Garden Station, Tildenville Outpost, and Apopka Station.
What are the best stops on the West Orange Trail?
Popular stops include Plant Street Market, Oakland Nature Preserve, The Backyard in Ocoee, and downtown Winter Garden.
Is the West Orange Trail good for families?
Yes, the trail is paved, wide, and includes parks, rest areas, and family-friendly stops along the way.
What activities are permitted on the West Orange Trail?
As a multi-use trail, bicycles, mobility devices, pedestrians, skates, skateboards, horses, and electric bikes (some restrictions apply) are permitted.
Are there facilities along the West Orange Trail?
There are multiple stations and outposts along the trail, including Winter Garden Station, Tildenville Outpost, and Apopka Station, offering amenities like parking, restrooms, and picnic areas.
When can the West Orange Trail be accessed?
The trail is open daily from sunrise to sunset.
Are pets permitted on the West Orange Trail?
Leashed pets are permitted on the West Orange Trail.
Where can more information or a map of the West Orange Trail be found?
Visit the West Orange Trail Information Page on the Orange County Parks & Recreation site.
Posted by Jen Durben on
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