Located south of downtown, this linear waterfront sequence along Hillsborough Bay stretches through the historic Hyde Park neighborhood. The park and boulevard was conceived between 1891 and 1893 when Chester W. Chapin purchased 110 acres just three miles south of the Tampa city limits. There he established a suburb and trolley car system which stretched from his development to the Ballast Point Pavilion pleasure ground. In 1907, Colonel Alfred Ruben Swann and Eugene Holtsinger continued the picturesque road, connecting it to downtown through their Suburb Beautiful residential district. By 1926, the entire length of the combined roadway was known as Bayshore Boulevard, with roadbeds flanking a trolley track median. Between 1934 and 1939 the Works Progress Administration funded extensive road renovations, including regrading, raising the seawall's height, and adding the signature Beaux Arts style balustrade. Trolley car service ended in 1946. In the 1960s, high rise residential buildings began to replace the private homes on the north side of the boulevard.
Today, the two-lane divided road runs 4.5 miles, and is composed of a 10-foot wide continuous sidewalk edged by the whitewashed masonry balustrade, providing uninterrupted views of the bay. Grass medians along the sidewalk provide a park-like continuity and are planted with irregularly-spaced palm trees. Medians also separate the two wide road beds, and are planted with grass and palm trees where space allows. Since 1989, the boulevard has been part of the city’s Greenway trail.