[3] The original segment of the trail from Venice to Palmer Ranch opened in 2008 and it was extended to central Sarasota in 2022.

The trail crosses Bahia Vista Street and Phillippi Creek before turning west toward downtown Sarasota.

[7] It heads north through Deer Prairie Creek Preserve before turning west and paralleling Interstate 75 for over almost four miles.

The railroad was used by cadets and faculty of the Kentucky Military Institute for winter classes from 1933 to 1970, transported patients to Fred H. Albee's Florida Medical Center from 1932 to 1942, transported goods and servicemen to Venice Army Air Field during World War II, and used by Ringling Bros. and Barnum & Bailey Circus, which was headquartered in Venice from 1959 to 1992.

Owing to decreased demand for service and the heavily deteriorated condition of the tracks and bridges, CSX Transportation and Seminole Gulf Railway, who had been leasing the line from CSX since 1987, came to an agreement with Sarasota County to abandon the railroad line south of Palmer Ranch.

[11] The original 10-mile (16 km) segment of Legacy Trail from Venice to Culverhouse Nature Park near Palmer Ranch opened to the public on March 28, 2008.

In early 2017, Seminole Gulf Railway and CSX announced their intention to abandon an additional 9 miles (14 km) of the remaining southern segment of the railroad up to a point just south of Fruitville Road.

In December 2017, Sarasota County, in conjunction with The Trust for Public Land, purchased and acquired 2.7 miles (4.3 km) of the former railroad corridor right of way for $7.9 million, which extended the county's ownership of the corridor up to Ashton Road, approximately one-half mile (0.80 km) north of Clark Road.

[15] In November 2018, Sarasota County voters approved a referendum to acquire and improve 6.3 miles (10.1 km) of the former railroad corridor, extending the trail and constructing the North Port Connector.

[16] By early 2020, Seminole Gulf removed tracks and signals from the corridor, and construction for the trail expansion started shortly after.