Masonry began in what is now the 18th Masonic District of the Grand Lodge of Florida in January, 1868, with the creation of Leesburg Lodge No. 58 in the city of Leesburg in Sumter County. Five years later, Ft Mason Lodge No. 65 was created in February, 1873, at Fort Mason in Orange County. In January, 1885, Eustis Lodge No. 85 was created in the city of Eustis, also in Orange County.

In January, 1886, three new lodges were chartered: Penninsular Lodge No. 88 in the city of Tavares in Orange County, Wildwood Lodge No. 92 in the city of   Wildwood in Sumter County, and Altoona Lodge No. 93 at the city of Altoona in Orange County.

On May 27, 1887, Lake County was formed from pieces of Orange and Sumter counties. At that time Lake County included Leesburg Lodge No. 58, Ft Mason Lodge No. 65, Eustis Lodge No. 85, Penninsular Lodge No. 88 and Altoona Lodge No. 93.

In 1888, a fire destroyed Penninsular Lodge and a new charter was issued. In 1890, Ft Mason Lodge changed its name to Umatilla Lodge to match the name of the town in which it was now located. Both Altoona and Penninsular Lodges  surrendered their charters in 1891.

Mascotte Lodge No. 190 was formed in January, 1910, in the town of that name. Clermont Lodge No. 226 was formed in that town in January, 1914. Tavares Lodge No. 234 was formed in January, 1916 and Mt Dora Lodge No. 238 in January, 1917.

In 1925, Mascotte Lodge was moved three miles east to the city of Groveland and became Groveland Lodge No. 190.

When the Grand Lodge of Florida realigned its zones and districts in 1993, the 18th Masonic District was formed to include all of Lake County and Wildwood Lodge No. 92 in Sumter County.

The latest addition to the 18th Masonic District was Villages Lodge No. 394 which was chartered in June, 1998, at The Villages.

Masons of the 17th District formed a Masters And Wardens Association to help coordinate the Masonic activities of the District. Membership was open to the Masters and Wardens of each Lodge with each Lodge having a maximum of three votes on any question. Other Master Masons were encouraged to attend meetings, but had no vote on matters brought before the Association.

When the 18th Masonic District was formed, the Association was reconfigured to allow all Master Masons of the District to join and have a vote in matters brought before the Association. Its name was officially changed to the 18th Masonic District Association.

In 2012, M∴ W∴  Glenn Phillips gave the 18th Masonic District the Moniker of “Grand 18th.”