Lake Lily Drive was the first direct route from Northeast Florida to Maitland, following Maitland Avenue around the west side of Lake Lily and continuing south on what is now Highway 17-92. During the Second Seminole War, the United States Army used this trail to connect the forts along its route. Fort Maitland was built in 1838 on the west shore of Lake Maitland, a day's march from Fort Mellon in Sanford. The fort was named for Captain William Seton Maitland, who was cited for bravery in a battle in 1836 and died in 1837 from wounds received there. Located south of present Fort Maitland Park, the fort remained in use only until 1839. In 1915, Orange County paved the route with bricks, creating Florida's first grouted brick road. The road later became part of the Dixie Highway, which opened in 1925 and ran from Sault Ste. Marie, Michigan, to Miami. In 1927, it was joined to the Black Bear Trail at Lake Lily, and both names described the road from that point south. The bricks were covered by asphalt in the 1960's, and in 1998 the asphalt was removed and the Maitland Historical Society restored the bricks with assistance from the City of Maitland and the Florida Department of State.