The 'beginnings' of what would become Whitesboro, was  a settlement established on "Wolf Path".  The area was called Wolf Path because the path bordered the cross timbers where wolves found protective cover that roamed the headwaters of the Trinity Valley and Red River Valley.  It also was part of the California trail used by many headed for California in search of fortune.  Wolf Path is now Main Street in Whitesboro.

Some families, arriving from Missouri, settled on Jordan Creek, about 4 miles south of the present town of Whitesboro in November 1845 prior to Captain White's arrival.  These families were the:

• Elizur D. Webster family
• Charles Wheelock family
• Myron Mudgitt family
• Frank Carpenter family
• Dr. Leaky family
• Widow Middleton
• Widow Underwood
  

Loneliness and fear of attack by Indians led to the founding of White's Colony, which today is this busy west Grayson County city.  In 1848, Capt. Ambrose B. White arrived in this area from Springfield, Illinois, with his wife and four children. The family settled on the old Wolfe Path between the Red River and the Trinity. Mr. and Mrs. White had met during the Blackhawk War when she and her mother molded bullets for the soldiers.  Capt. White built an inn. His inn was the center of cattle and buffalo hide trading between Indian Territory and Texas.  This inn would become the center of the town of Whitesboro.

Because of the isolated conditions when people became (sic) moving into this area, they settled near Capt. White and the settlement became known as White's Colony.  However, Capt. White gave the community the name of Westview Inn, which he had established, and when a post office was applied for at the end of the Civil War, the post office gave the town its present name of Whitesboro.

The Baptists organized the first church here in 1856 and the first school was taught in a log cabin by a Miss Brink and her brother. During the Civil War, a Mr. Taylor, who was exempt from service because of a lame leg, taught school at Capt. White's Westview Inn.

Whitesboro got its first charter in 1873.  The population was estimated to be around. In 1887, when the population had topped 1,000, a second charter was obtained and the town still operates under it.
Crops produced were cotton, corn, grain.  Peanuts were also a money crop and a Peanut Festival is celebrated in Whitesboro annually.
A log Masonic hall was erected after the war and it became the first public school building. In 1889 the first brick building in Whitesboro was constructed and was the school house.

Whitesboro became a boom town for the first time when the Butterfield Company of Boston placed its Overland Mail stage lines in operation as a stage stop. A stage stop on the western route of the Butterfield Stage Line prior to the CIvil War was located where the Whitesboro schools are located today.
The Texas and Pacific Railroad Company was given, in deed, one hundred acres of land by the citizens of Whitesboro in 1877.  The Company received the right-of-way from Mustang Creek, six miles east, and to and through the town. Also included was land for the purpose of a depot.  The first depot, a small wooded structure, was built in 1878 which provided employment for eighteen men.  A $35,000 building was erected by the Texas and Pacific Railroad in 1900.  The structure was jointly shared with the Missouri, Kansas and Texas Railroad Company.  This depot was demolished in 1972.

Whitesboro, a town some 15 or 18 miles from the Infant Wonder, Denison, having been reached by rail is now spoken of as a suburb of the latter city.  (Brenham Weekly Banner, March 28,1879)

Whitesboro was the first town in Grayson County to install a water system.
Today a community of over 2,000 people, Whitesboro was established at a time where there was only one log cabin between here and Sherman. (The Denison Herald, Sunday Morning, June 25, 1972)

Early doctors were:

• Dr. Trollinger
• Dr. Graves
• Dr. Henry T. Trollinger
• Dr. A. M. Huff

Sources
The History of Grayson County Texas by Grayson County Frontier Village, c1979, pgs91-93
The Denison Herald, Sunday Morning, June 25, 1972