It was named for town site developer Charles N. Haskell, who would become the first governor of the State of Oklahoma in 1907.

Haskell was founded about one and a half miles northeast of the Muscogee (Creek) Nation town of Sawokla, which already had a post office, a store and a cotton gin.

The original 80 acres (32 ha) tract had been allotted to Amos Rolland, a member of the Creek Nation.

Haskell's first post office was established in 1902, with Nat Lambertson, owner of a new hardware and general store, appointed as first postmaster.

[citation needed] The railroad enabled farmers near Haskell to ship their produce (grain, hay, corn, melons and cotton) to northern and eastern markets.

The Robertson Memorial Presbyterian Church, named for a noted missionary family who had lived in the area, was built in 1909.

This sparked a period of prosperity, and Haskell soon could boast of improvements such as paved streets, concrete sidewalks, electric lights, natural gas lines, and water works.

[5] Completion of the Tulsa-Muskogee Turnpike in 1969 bypassed Haskell and diverted much road traffic from U.S. Highway 64.

[5] In March 2024 by a vote of the citizens, Haskell changed from a Town to a City Manager form of Government.

[5] According to the United States Census Bureau, the town has a total area of 2.2 square miles (5.7 km2), all land.

[12][13] The Arkansas River, just to the east of town,[7] also offers fishing opportunities for species like catfish, though access there is typically had through private lands.