Founded in 1879, when old-timers traveled by wagon and camped near Sherman to reminisce about days of Republic of Texas, the frontier, and the Southern Confederacy.  W.W. Wheat was the first presiding President of the Old Settlers Association of North Texas.

Speakers at first meeting included Mrs. Julia Shannon King (daughter of donor of part of Sherman townsite) and Mrs. Sophia Porter, who came to Grayson County in 1838 as bride of Holland Coffee, owner of Indian trading post at Preston Bend.

The Association was incorporated on Oct. 31, 1898. Having met in various groves, it purchased this popular and accessible site in 1899 as permanent headquarters. Financing was hampered by adversities (bad weather, smallpox, power failure on commuting streetcar line), but purchase cost was paid by 1909. The auditorium, named for the veteran association secretary Jesse Loving, was built in 1923.

Noted orators at annual conventions have included statesmen Joseph Weldon Bailey, James S. Hogg, Roger Q. Mills, Sam Rayburn, John H. Reagan, Morris Sheppard.