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This community formed near a large post oak grove that was a prominent landmark for pioneer travelers and a lookout point for Native Americans. 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.
The 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 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.