Littlefield did not prosper immediately after the war. His attempts at farming foundered. River floods in 1869 and 1870 took him to the brink of bankruptcy. It was not until 1871 that he speculated in the cattle market and made a profit. Over the next several years, he drove large herds of beef cattle from South Texas to Kansas. With proceeds from his cattle drive, Littlefield opened a dry goods store in Gonzales in partnership with J. C. Dilworth. He obtained ranches in Caldwell and Hays and later Mason, Kimble, and Menard counties. He established or purchased such outfits as the LIT Ranch in the Texas Panhandle, the Bosque Grande in the Pecos River Valley and the Four Lakes on the Plains, both in New Mexico, the Yellow House on the Texas South Plains, and the Mill Creek and Saline ranches in the Texas Hill Country. At one time, his cattle, branded LFD, roamed over an area of eastern New Mexico the size of the state of Rhode Island.