Settlers first arrived in this area in the 1870s; among them was the McLeod family, after which the settlement was briefly known as "McLeod Settlement." A post office, originally to be called Blue Pond but finally named Pinan, was established in 1880 with William C. McLeod as postmaster, but it lasted less than a year.

Excitement came to the settlement in 1884 when the South Florida Railroad was constructed. A townsite was surveyed and in 1885 a the new McLeod post office opened, though it almost immediately was renamed Macon. By 1886, Macon had 130 residents as well as six stores, a school, church, and hotel. In 1887, the narrow-gauge Orange Belt Railway was built through town, crossing the South Florida at almost a right angle and linking Macon to nearby Lacoochee. In 1895, the Orange Belt was acquired by Henry Plant (who already owned the South Florida) and work began on converting the line to standard gauge. The original depot was demolished, and the new Trilby townsite platted - named for the George du Maurier novel that gained popularity the previous year (the street names in the new townsite were even named after the characters from the novel).

Before long, a substantial commercial district developed. The rail yard was the third largest in Florida, and even after Plant's death and the sale of the Plant System to the Atlantic Coast Line Railroad in 1902 Trilby's prominence was assured due to its location. This boom was magnified in 1922 when the Cummer Sons Cypress Company opened their new sawmill in Lacoochee and many workers moved to both towns. In the end, this would prove to be the beginning of the end for Trilby when the other town began to overshadow it. The Trilby State Bank went into receivership in 1924, and a large fire on May 29, 1925 destroyed much of the business district.

Today Trilby is merely a shadow of its former self. Few, if any, traces remain of the once prominent business district. Service on the east-west line (former Orange Belt Railway) ended in 1972 and the tracks were removed in 1978, followed by the north-south line (former South Florida Railroad) in 1987; the latter is now part of the Withlacoochee State Trail.

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