The Haven Villa Corporation salesmen lined up in 1925 to greet prospective customers from the North on special trains into downtown. The Snell Bank with its clock on Central Avenue can be seen on the left. (State Archives of Florida)

Located 51 miles east of Tampa, this city of nearly 45,000 residents was born as a result of Henry Plant’s construction of the South Florida Railroad’s Bartow Branch in 1884. Platted that same year, the city quickly grew up around the railroad, which served as an economic and vital transportation link for the local citrus industry. By the time of its incorporation in 1911, the city’s downtown district was anchored by citrus packing houses and associated industries lining the railroad through the center of town.

During the late 20th century, Downtown Winter Haven’s economic character changed with the opening of the Winter Haven Mall, citrus freezes that crippled nearby packinghouses houses and juice processing plants and the 1986 abandonment of the railroad that originally gave it life. Left was a corridor of deteriorating vacant properties in the center of the city.

A photograph of the abandoned railroad line just north of Downtown Winter Haven in 1996. During the early 2000s, the former railroad corridor was converted into a trail system. (Ennis Davis, AICP)

Dreams of an economic rebirth received a significant boost in 1995 with the establishment of Main Street Winter Haven, Inc. when the city was designated as a Florida Main Street community. Additional visioning efforts lead to the creation of the “Our Future by Design: A Greater Winter Haven Community” plan in 2000.

In the 21st century, revitalization strategies following the National Main Street Approach lead to the incremental implementation of several initiatives including streetscapes, right-sizing streets, establishing downtown facade guidelines, a facade grant program and investing in active public spaces around the former railroad reborn as the Chain of Lakes Trail. In recent years, the blighted scene of the late 1980s and early 1990s has been reborn as pedestrian and bicycle friendly retail and dining environment centered around well maintained active public and central gathering spaces.

Now revitalization of this former citrus town is no longer a topic only known to residents of Polk County. Recently, it was selected by APA Florida as its 2019 Great Places in Florida People’s Choice Winner. Modeled after APA’s Great Places in America program, the award represents an annual selection of places that represent the gold standard in terms of having a true sense of place, cultural and historical interest, community involvement and a vision for tomorrow. Previous winners over the past five years include Winter Garden, Pensacola, Cascades Park, Fernandina beach and Mount Dora.

A Visual Tour of Downtown Winter Haven

Pope Avenue Historic District

There are several residential historic districts within walking distance of downtown. The Pope Avenue Historic District is an example one block west of Central Park.

The Haven Condominiums on 6th Street NW was originally known as the Haven Hotel. It came as a result of Winter Haven residents R.H. Ross and J. Walker Pope promoting the idea in 1921 that the city of then 1,600 residents, needed a good hotel. The Haven Hotel opened in 1924 with 180 rooms. By the 1960s the building had fallen into decline. In 1982, it was restored and converted into 55 condominium units.

The Museum of Winter Haven History is located in the former Women’s Club building at 660 Pope Avenue. It features photographs and memorabilia donated by the citizens of Winter Haven.