Gregg and his men reached Raymond on May 11, expecting to find Colonel William Wirt Adams's Confederate cavalry in the town; Adams's men were to conduct reconnaissance. Instead, the only Confederate force in Raymond was a small command of 40 cavalrymen and a separate five-man detachment. Gregg sent the 40-man unit down the road towards Utica, while keeping the five men for courier service. Adams later sent a unit of 50 cavalrymen to aid Gregg; they arrived that night. On the morning of May 12, the scouting force soon reported approaching Union soldiers, and Gregg, still anticipating only a single Union brigade, prepared for battle with a force numbering around 3,000 to 4,000 men. The scouts had been unable to provide an accurate count of Union strength. Believing that he could easily defeat the approaching enemy force, Gregg responded aggressively. He ordered Colonel Hiram Granbury to take the 7th Texas Infantry Regiment and the 1st Tennessee Infantry Battalion to a rise near the junction of the roads to Utica and Port Gibson. The Texans were to attract Union attention and draw them into a cul-de-sac-shaped portion of Fourteenmile Creek. Colonel Calvin H. Walker and the 3rd Tennessee Infantry Regiment were sent to the back side of some high ground northeast of the brigade over Fourteenmile Creek. The 50th Tennessee Infantry Regiment and the 10th and 30th Tennessee Infantry Regiment (Consolidated) moved down the Gallatin Road to the left. Gregg's plan was to contest his line with Walker's and Granbury's men and then have the Tennesseeans down the Gallatin Road conduct a flanking attack against the Union right. Hiram Bledsoe's Missouri Battery and its three cannons was positioned with the 1st Tennessee Battalion and had orders to fire on any attempts to cross the bridge over the creek on the Utica Road. The 41st Tennessee Infantry Regiment was held in reserve in Raymond.