over South Creek along the trail near Oscar Scherer State Park The railroad line from School Avenue (on the trail's spur) to a point near Beneva Road was initially built in 1903 by
Seaboard Air Line Railroad (via their
Florida West Shore Railway subsidiary) and was extended south from there to Venice in 1911. Track from Shade Avenue north to Fruitville Road was built in 1927 by the
Atlantic Coast Line Railroad (via their
Tampa Southern Railroad subsidiary). The Atlantic Coast Line tracks ran directly beside the Seaboard Air Line tracks between Shade Avenue and Beneva Road before the former continued east out of the city. The two parallel railroad lines were consolidated onto the route the trail follows today in 1967 when the Atlantic Coast Line and Seaboard Air Line merged and became the
Seaboard Coast Line Railroad (which later became part of
CSX Transportation). In Venice, the railroad line was integral to the city's history and benefited the city's economy. 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 , and used by
Ringling Bros. and Barnum & Bailey Circus, which was headquartered in Venice from 1959 to 1992. The circus was the last consistent service the rail line carried. 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. In return, Sarasota County, in conjunction with
The Trust for Public Land, purchased and acquired the right of way in December 2004 for $11.75 million to use as a public recreational trail. The original segment of Legacy Trail from Venice to Culverhouse Nature Park near Palmer Ranch opened to the public on March 28, 2008. In 2011, a pedestrian overpass was built to carry the trail over the
U.S. 41 Venice Bypass, a major six-lane highway. The $3.1 million overpass is tall, spans , and was built with federal stimulus funding. Another
pedestrian overpass constructed by
FDOT over
Laurel Road started construction in November 2017 and was completed in late 2018. In early 2017, Seminole Gulf Railway and CSX announced their intention to abandon an additional 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 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 north of
Clark Road. In November 2018, Sarasota County voters approved a referendum to acquire and improve of the former railroad corridor, extending the trail and constructing the North Port Connector. By early 2020, Seminole Gulf removed tracks and signals from the corridor, and construction for the trail expansion started shortly after. The segment from Sawyer Loop Road to Ashton Road opened on October 7, 2021. The final segment from Bahia Vista Street to Fruitville Road opened on March 3, 2022. The North Port Connector opened on September 9, 2022. The short connector linking the trail's spur at School Avenue to the Alderman Street Multi-Use Recreational Trail was built by the city of Sarasota in 2025. ==Future==