Winter Haven Chain of Lakes loop via the Chain of Lakes Trail
Winter Haven Chain of Lakes loop via the Chain of Lakes Trail
4.7
(8663)
18,170
riders
02:04
49.7km
100m
Road cycling
This moderate 30.9-mile road cycling loop on the Chain of Lakes Trail offers diverse scenery and unique landmarks in Winter Haven.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
3.87 km
Highlight (Segment) • Trail
Tip by
14.7 km
Highlight • Structure
Tip by
29.0 km
Highlight • Lake
Tip by
49.7 km
End point
Parking
Way Types & Surfaces
Way Types
20.0 km
16.1 km
7.13 km
6.47 km
106 m
Surfaces
38.9 km
10.7 km
181 m
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Elevation
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Weather
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Today
Thursday 28 May
32°C
23°C
83 %
Additional weather tips
Max wind speed: 15.0 km/h
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This route was planned by komoot.
The full loop, which is about 49.75 kilometers (30.9 miles) long, typically takes around 2 hours and 4 minutes to complete on a road bike. This duration can vary based on your cycling speed and how often you stop.
Yes, the trail is largely flat and considered a good option for beginners. While there are some slight inclines over bridges, the overall experience is accessible for cyclists of all fitness levels.
Convenient parking is available at Downtown Trailhead Park in Winter Haven. This location also offers restrooms, a playground, and a splash pad, making it a great starting point.
The route is predominantly flat and paved, following an abandoned rail corridor. You'll encounter dedicated bike bridges over busy streets, contributing to a mostly relaxed cycling experience. Some sections have slight inclines due to these bridges.
You'll enjoy views of several lakes in the Chain of Lakes, including Lake Silver, Spring Lake, Lake Ida, and Lake Conine. The trail passes through a mix of parks, residential areas, and some industrial sections. A unique feature is a section that runs directly under and through the Chamber of Commerce building in Winter Haven. You'll also pass near Legoland Florida and Lake Hamilton.
While the trail can be enjoyed year-round, the cooler, drier months from late fall to early spring (roughly November to April) are generally preferred for cycling in Florida to avoid the peak heat and humidity of summer.
The trail itself is generally dog-friendly, but dogs should always be kept on a leash. Be mindful of other cyclists and pedestrians, and ensure you clean up after your pet.
No, there are no specific permits or entrance fees required to access and cycle on the Chain of Lakes Trail.
Yes, the trail connects to downtown Winter Haven, offering various dining options. At the Lake Alfred end, you can find amenities like a Dunkin' Donuts, 7-11, and a diner for refreshments.
While dedicated bike bridges handle most major road crossings, there are still some street crossings. One notable section at Avenue T in Winter Haven requires careful navigation of traffic. Some users have also noted concerns regarding safety in less-developed or industrial sections, particularly after dark.
While the Chain of Lakes are known for water activities, the area is quite developed, so opportunities for natural wildlife viewing are less common. You might see some birds or small animals in the park sections or near the lakes, but it's not primarily a wildlife-spotting trail.