CThe Chain of Lakes Trail in Polk County is primarily an urban trail that runs over 3 miles from Lake Alfred on its north end south to Winter Haven. The trail surface is asphalt and concrete. Parts of the trail through Lake Alfred and Winter Haven are on a sidewalk. In April 2017, a new bridge over Hwy. 92 opened that makes this segment of the trail safer for pedestrians and cyclists. There are also bridges spanning Lake Conine Canal and Havendale Blvd. The trail name derives from the path it takes between a series of lakes.

This is not a scenic trail. Its main interest is in the history encountered along its length. In 1885 a railway was established between Winter Haven and Lake Alfred. In 1925 the National Railroad station was built on 7th Avenue, SW, in Winter Haven. This station building still stands near Chain of Lakes Downtown Trailhead Park and is currently used as the Winter Haven Area Transit Bus Terminal. Parking is available at the terminal.

The railway was deactivated in the 1970s and the corridor sold to the City of Winter Haven and the CSX Corporation. In 1998, the city and the State of Florida purchased the northern portion owned by CSX to build a pedestrian and biking trail. The trail was opened 10 years later in 2008.

The area that is now Downtown Trailhead Park hosted the Florida Citrus Festival in the 1920s and 1930s. Thousands of people attended this festival including President Calvin Coolidge. In 1944, during WWII, the site was converted to a prisoner of war camp that held 250 German prisoners. Today this recreational park contains a playground, water park, and picnic area. It also serves as a trailhead for the Chain of Lakes Trail. Restrooms are available there.

From Trailhead Park, the trail extends south to Central Avenue. This section of the trail traverses a plaza and is bordered by sculptures, trees, and benches. Across the street from the plaza on its west side is located another historic structure, Derry Down. According to a sign on its front lawn, this teen club was opened in 1964 by Winter Haven businessman Bob Parsons as a performance venue for his stepson Gram Parsons and other local musicians as well as traveling performers. Gram Parsons began his career here with a folk group called The Shilohs and later played with The Byrds and The Flying Burrito Brothers. In 2013 the building was to be demolished, but a local preservationist sounded the alarm and the owner instead donated it to a local group “to restore…and preserve its legacy by nurturing new artists.”