Delaware Bend was settled 23 miles north of Whitesboro in 1836. The name was derived from one of the two remaining Indian villages in Texas. The Delaware Bend Community consisted of three smaller communities: Upper Bend, Lower Bend, Prairie. It was located in both Grayson County & Cooke County. Fannin County was established in 1837; the Lower Bend & Prairie became part of Fannin County. Before the U.S. Government purchased the land to make way for the waters of Lake Texoma, Riverside School was the focal point of the Upper Bend; Hughes Chapel Church of the Lower Bend, and Prairie Valley School on the Prairie. For many years there were no church buildings. During the summer brush arbors were built for meetings. Limited facts about Delaware Bend were recorded since it was populated with Indians long after the beginning of Grayson County. Early white settlers immigrated from Europe and Germany. Many spoke no English and led a somewhat secluded life for the first generation. 
Col. James Bourland, a military commander for the Confederacy, was a large land owner in both the Delaware Bend and Walnut Bend areas. The Bourland Plantation home was built by slave labor. It was used as a home and a fort for protection from the Indians. Under the kitchen was a cellar with underground tunnels. The land eventually became part of the Burrell Ranch.
Millard
Ragsdale moved to the area in 1860 at the age of four years with his family from Kentucky. He was a landowner, farmer,
store operator and ferry boat operator. He resided at Delaware Bend for
83 years.
John W. Shwadlenak owned and operated the Tipton Ferry when Texoma was formed. John Shwadlenak II built a gin on the Shwadlenak homeplace. An Indian trail beside the home led to a whiskey still.
David
D. (Shar) Thorn owned 1500 acres of land. He had a mill and operated a store
for the convenience of tenants who rented land from him. The
Orlena cotton gin, located on the Cooke & Grayson County line, was
moved to the Thorn farm in Grayson County.
The Charlie Sissney family settled in Delaware Bend in 1909 from Oklahoma. His son, Tom Sissney, became the proprietor of the Orlena store after Millard Ragsdale. For many years, it was the only store in Delaware Bend.
Local Cemetery was named Howard Cemetery. It is also known as the Washington Cemetery. 
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