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The Seminole Wekiva Trail has been built for the most part on the roadbed of the Orange Belt Railway. This railroad was the lifeline of the area from Sanford to Lake Apopka from 1885 through the early part of the 20th century. Starting at Lake Monroe it tied together what is now the western part of Seminole County with stops at Sylvan Larke, Paola, Island Lake, Glen Ethel, Groveland, Palm Springs (all farming settlements along the Longwood Markham Road), as well as Granada (as this area was called), Forest City, and Toronto, a distance of 18 miles. By 1888 the line extended to Pinellas Point, on the Gulf of Mexico. At that time it was the longest narrow gauge railroad in the country, extending for 117.68 miles, a status it held until 1897.
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Peter A. Demens, the prosperous owner of a sawmill in Longwood, was the driving force behind the building of the railroad. In 1885 he took over the charter of the Orange Belt Railway just underway in Lake Monroe, in payment for cross ties from his mill. The charter gave permission to build a railroad from Monroe (now Lake Monroe) to Oakland on the south shore of Lake Apopka, a distance of 35 miles. It was completed in November of 1886. A man of vision and optimism, Demens overcame grave financial difficulties to extend the line to the Gulf coast. This was accomplished in 1888 after a series of contractual and financial crisis were averted with help from the meat-packer Phillip Armour and Philadelphia financiers. Point Pinellas, the southern terminus of the line, was given the name St. Petersburg in honor of Mr. Demens' native city in Russia. In bankruptcy in 1893, the line became part of the Plant System and was renamed the Sanford and St. Petersburg Railway.