Confederate Col. A. W. Reynolds' brigade (Maj. Gen. Carter Stevenson's division), escorting a large 200-plus wagon train filled with 350 tons of food and ammunition passed this road intersection (about 4.6 miles east-northeast of the Old Court House at Vicksburg - historic Benton road is present-day Oak Ridge road/historic Bridgeport road is present-day Freetown road) en route to Vicksburg sometime during the afternoon of May 17, 1863, after crossing the Big Black River at Bridgeport where his men had a sharp skirmish with Union cavalry.

Union Maj. Gen. William T. Sherman (XV Corps) and Maj. Gen. Francis Blair were riding near the head of Blair's division when they reached the Benton road - Bridgeport road intersection at about 10:00 a.m.. Maj. Gen. Frederick Steele's division was close behind, but Brig. Gen. James M. Tuttle's division was perhaps two hours away. At this point, Sherman halted the advance to await the arrival of Tuttle's division, but in the meantime he sent a powerful combat patrol north on the Benton road. He knew the Benton road communicated with the Confederate defense system at Snyder's Bluff and Drumgoluld's Bluff, and did not want to be taken by surprise by an attack from the Confederate garrison at those places. He had two priorities: first, to close all roads out of Vicksburg to the north, thus preventing the escape of any Confederate troops still in the town; and second, to make contact with Rear Adm. David D. Porter and the Mississippi River.

Maj. Gen. James B. McPherson's XVII Corps followed closely on Tuttle's heels at this point.

This site has local significance because of its association with military activities and events that achieved or affected important local objectives of the Vicksburg campaign.