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Routes
Road cycling routes
United States
Florida
Orange County
Winter Garden

West Orange Trail – Downtown Winter Garden loop from Winter Garden

Routes
Road cycling routes
United States
Florida
Orange County
Winter Garden

West Orange Trail – Downtown Winter Garden loop from Winter Garden

Moderate

4.6

(9588)

13,211

riders

West Orange Trail – Downtown Winter Garden loop from Winter Garden

02:07

51.7km

170m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: April 30, 2026

Tips

Includes a segment in which cycling is not permitted

After 50.2 km for 92 m

Waypoints

A

Start point

Parking

Get Directions

1

4.29 km

West Orange Trail

Highlight (Segment) • Trail

The West Orange Trail totals over 20 miles and is paved the entire way. The trail is normally over 10 feet wide and is really popular for flat running, walking, and biking. There are a bunch of different trailheads, so you can start your tour from a number of different places.

Tip by

2

8.13 km

Friendly place. If you are a C2C thru cyclist, they will take your pic and post it.

Tip by

3

8.66 km

they are just after the station

Tip by

4

16.1 km

Downtown Winter Garden

Highlight • Settlement

The historic town of Winter Garden holds many hidden treasures wrapped in its small town Florida charm. There are stories of train workers spitting tomato seeds into the soil and to their surprise it plants would grow even in the winter. Hence, the name: Winter Garden.

Tip by

5

16.3 km

Downtown Winter Garden

Highlight • Settlement

The historic town of Winter Garden holds many hidden treasures wrapped in its small town Florida charm. There are stories of train workers spitting tomato seeds into the soil and to their surprise it plants would grow even in the winter. Hence, the name: Winter Garden.

Tip by

6

50.3 km

Newton Park Pier and Playground

Highlight • Rest Area

Fenced playground with lots of play equipment. Parking lot and toilets directly adjacent.

Translated by Google •

Tip by

B

51.7 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

30.1 km

15.3 km

3.24 km

2.32 km

746 m

Surfaces

46.6 km

3.34 km

1.54 km

189 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

Today

Sunday 5 July

34°C

25°C

83 %

Additional weather tips

Max wind speed: 11.0 km/h

to get more detailed weather forecasts along your route

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Description

If you're looking for a solid road cycling workout that connects you with a charming Florida town, the West Orange Trail – Downtown Winter Garden loop from Winter Garden is definitely worth your time. This moderate route covers 32.1 miles (51.6 km) with 562 feet (171 metres) of elevation gain, and you can expect to complete it in about 2 hours and 6 minutes. It's a fantastic option for cyclists who appreciate a well-maintained path and the convenience of urban amenities.

What to expect on West Orange Trail – Downtown Winter Garden loop from Winter Garden

This loop offers a smooth ride, primarily along the dedicated West Orange Trail, which is known for its excellent pavement and generally flat profile, making the moderate difficulty more about distance than strenuous climbing. You'll experience the classic Florida trail vibe, likely passing under canopies of trees and through open sections, with the highlight being the connection to Winter Garden's vibrant downtown. The route is well-suited for road cyclists looking for a consistent pace and a chance to explore local points of interest without significant technical challenges.

Planning your visit

Given Florida's climate, the best time to visit for cycling is typically during the cooler months, from late fall to early spring, to avoid the intense summer heat and humidity. If you're cycling during warmer periods, plan your ride for early mornings or late afternoons. Parking for West Orange Trail Winter Garden is generally available near the downtown area, but it's always wise to arrive early on weekends to secure a spot. Remember to carry plenty of water, especially on longer rides.

Trail details

  • Distance: 32.1 miles (51.6 km)
  • Elevation gain: 562 feet (171 metres)
  • Difficulty: moderate
  • Estimated time: 2 hours and 6 minutes

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