Revitalization Around Trails

In 1884, Henry Bradley Plant’s South Florida Railroad constructed a railroad spur to connect Bartow with the main railroad line running between Tampa and Orlando. What became Downtown Winter Haven would rise with the growth of the citrus industry along the railroad corridor and decline with the railroad’s mid-1980s abandonment. As a part of the state’s Rails to Trail program, the state agreed to acquire 4 miles of former rail right-of-way from CSX for $1.4 million to convert the corridor into Polk County’s second rail trail. Since 2000, the Chain of Lakes Trail has been built to connect Downtown Winter Haven with the neighborhing city of Lake Alfred to form a linear recreational green space in the city and serve as an economic anchor for a 21st century city.

Tupelo Vue is a 70 unit luxury apartment development built adjacent to the Chain of Lakes Trail by the Pinnacle Housing Group in 2015.

Olde Towne Square was constructed in 1928. It was the home of the city’s post office until 1962. Today, this arcade is home to a number of small offices, retailers and restaurants.

On December 20, 1964, Bob Parsons established the Derry Down in this small building. A teen club and music venue, it served as a performance venue for his stepson Gram Parsons and his band, The Shilos. Since his death at Joshua Tree in 1973, Parsons has become widely known as a founder of country rock and alt-country genres and as the father of Cosmic American Music. Once eyed for demolition, the building’s owner Winter Haven-based Six/Ten, LLC. donated the structure after realizing its historic significance. In 2014, a Main Street Winter Haven Inc. initiative to called The Derry Down Project began to renovate the structure back into a music venue and event space. Now the fully restored building provides a place for musicians of all levels to gather and play.

Just south of Central Park a warehouse district developed in the early 20th century that catered to the city’s burgeoning citrus industry. The district’s early industrial companies include the Winter Haven Packing Company, Winter Haven Water, Light, & Ice Company, P.A. Gerke Cigar Factory, Wilson & Toomer Fertilizer Company, Winter Haven Steam Laundry and the Dixie Canning Company. By the 1990s, the district had declined into a collection of vacant and underutilized buildings clustered around an overgrown abandoned railroad corridor. Following a realignment of U.S. 17, which had long divided this district from the downtown core, many buildings have been renovated and adaptively reused.

Recently renovated warehouses once occupied by the Wilson & Toomer Fertilizer Company.

The Bike Shop of Winter Haven and N+1 Coffee share a space that was once a BFGoodrich tire service center.

For a number of years, U.S. 17 was a busy highway that cut off Central Park from the south side of downtown. During the early 2000s, the four to five lane highway was realigned through the abandoned railroad corridor just south of downtown. Following the opening of the realignment, the former highway’s path (Avenue A SW and Third Street SW) has been right-sized to incorporate an extension of the Chain of Lakes Trail south of Central Park.

Avenue A SW through Downtown Winter Haven as a four lane thoroughfare in 2011. (Google Streetview)

Avenue A SW through Downtown Winter Haven in 2019 as a two lane street with a parallel shared use path.

In 2016, the city’s first craft brewery, Grove Roots Brewing Company, opened in a former garage warehouse renovated by Six/Ten LLC.

A 2008 view of the former warehouse that became Grove Roots Brewing Company. In recent years, Third Street SW was reduced from a four-lane roadway to allow space for on-street parking and a shared use path. (Google Streetview)