Scenic Street in Winter Garden

Hike the 41.4-mile West Orange Trail, a difficult route through Central Florida's towns, woods, and marshes with 677 feet of elevation gain.

This easy 3.5-mile (5.6 km) loop offers a delightful blend of small-town charm and natural Florida scenery, making it a perfect choice for a relaxed outing. You'll wander through the picturesque downtowns of Winter Garden and Oakland, passing historic buildings, shops, and tree-lined streets, with the West Orange Trail forming the backbone of your journey. Keep an eye out for the iconic clock tower in Winter Garden and the massive oak trees shading the streets of Oakland, creating a truly scenic street experience.

Planning your visit to this City Hall Scenic Street loop Winter Garden Oakland trail is straightforward, as it's easily accessible from both downtown areas. Parking is typically available in the charming downtowns, but arriving earlier in the day is advisable, especially on weekends. Since the route is well-integrated with urban amenities, you'll find plenty of opportunities for refreshments, and the paved surface makes it suitable for year-round enjoyment, though cooler months are often more pleasant.

What makes this route particularly notable is its seamless integration into the vibrant communities it traverses, earning Winter Garden the designation of a "Trail Town." The West Orange Trail, a world-class multi-use pathway, provides a smooth, flat surface with a negligible 24 feet (7 metres) of elevation gain, ensuring a comfortable 1 hour and 25 minutes of hiking. This makes it an ideal family-friendly hiking City Hall Scenic Street loop, offering a glimpse into the region's history as you follow old railroad alignments.