This community formed near a large post oak grove that was a prominent landmark for pioneer travelers and a lookout point for Native Americans. Dripping springs just north of the grove (now under water of Lake Ray Roberts) encouraged settlement, as did the rich black/sandy loam prairies to the east and the timber area to the west. The public square of the town was platted and laid out by George Newcomb on Christmas Day 1853, making it the oldest town in Denton County. Goods and lumber were hauled from Jefferson to supply the needs of the community until the Texas and Pacific Railroad came to the city.
A citywide effort to preserve buildings on the historic square, built between the 1870s and the 1890s, resulted in Pilot Point being named a Texas Main Street City. Visitors can find antique shops and cafes on the downtown square. The Farmers & Merchants Bank Building, of Richardsonian and Romanesque architecture, was used in the famous film Bonnie & Clyde and is now an art gallery.
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