George Washington Littlefield is one of the most interesting men in Gonzales' history. He was born in Panola County, Mississippi, June 21, 1842. His parents, Fleming and Mildred T. Littlefield, moved to Texas when George was only eight years old. He attended Baylor University until he joined the Confederacy in 1861 and served as Second Sergeant of Company I, 8th Regiment, Texas Cavalry, under the command of Colonel B.F. Terry. This unit was better known as Terry's Rangers. He was promoted to 2nd Lieutenant in 1862 and commanded his company at Shiloh and, after being promoted to Captain, led his troops during the capture of Murfreesburo. After being promoted to Major, Littlefield was severely wounded during the battle of Mossy Creek, Tennessee, and was cared for by his servant who had accompanied him from Gonzales. George's wounds took a long time to heal and he was forced to return home. Arriving back in Gonzales, he began farming. In January, 1863, he married Alice P. Tiller of Houston, born in Virginia, April 10, 1846, the stepdaughter of Whitfield Harrel. She and George had several children but they all died in infancy. In 1871 he engaged in the cattle business and became a merchant. He was successful at any business he pursued.
In 1871 George purchased the property where the house originally stood. There was a small house on the lot built by W.F. Laird about 1868 but it was apparently razed to allow construction of the Littlefield house. The appraised values from 1871 through 1886 indicate that the house went through several major changes. Although Littlefield moved to Austin in 1883, the last significant change to the structure was made in 1885, while he still owned the property. The Queen Anne style house was built on the lot that is now occupied by the C.E. Dilworth House. It was purchased by T.M. Harwood and moved to its current location in 1911.
After moving to Austin, Littlefield became a financial leader. He purchased the Driskill Hotel in 1896 and continued to own it until his death. He also owned a 1336 acre irrigated farm in New Mexico's Pecos Valley where he raised alfalfa for his ranch seventy-five miles to the east. On that ranch he maintained 60,000 head of cattle and, on another ranch of 120,000 acres, he maintained 12,000 head. He served as Regent of the University of Texas and willed $1,100,000 to the University. When he died in Austin, November 10, 1920, his estate was valued at $8,000,000. His will also directed that his faithful slave, Nathaniel Littlefield Stokes, be cared for by the Littlefield estate for as long as he lived. Nathaniel was to be provided $2 a week pocket money and, upon his death, be buried in the Littlefield burial ground with a tombstone.