Wesley H. Frey was born on October 14, 1842, in Tennessee to Thomas Jefferson Frey and Elizabeth Jane Farthing. His father was a farmer who owned $3,300 of real estate and $1,150 of personal property by 1860. The family was living in Robertson County, Tennessee, in 1850 and moved to Montgomery County sometime before 1860.
Frey enlisted in the Confederate army on November 18, 1861, and mustered in as a private in Company E of the 50th Tennessee Infantry. According to his service records, he was 5 feet, 5 inches tall, with dark hair and hazel eyes. Half of the regiment was captured at Fort Donelson in February 1862, but Frey managed to elude Union forces. The regiment also took part in the battles of Chickasaw Bayou, Chickamauga, and Missionary Ridge. Frey was captured at Missionary Ridge on November 25, 1863, and sent to Rock Island prison camp in Illinois. In February 1864, he confessed that he was "think[ing] a greate deal about taking the Oath and quiting the ware and com[ing] hom," but he was "in daut and dont know what to do." He finally swore an oath of allegiance to the United States on April 10, 1865, claiming that he was “Tired [of] fighting for C.S.A.”
Frey returned to Montgomery County after the war, and he married Matilda Elizabeth Jones soon afterward. They had at least eleven children: Ida, born around 1867; Walter, born around 1869; Emma, born around 1872; Jane, born around 1873; Lilian, born around 1874; Alice, born around 1879; Wesley, born around 1880; Charles, born around 1882; Nellie, born around 1884; Leslie, born around 1886; and Thomas, born around 1890. In 1870, the family owned $1,500 of real estate and $600 of personal property, and they employed a Black “Domestic Servant” named Martha Bryant. Matilda died in Montgomery County on December 6, 1891, and Frey remarried around 1894. He remained in Montgomery County for the rest of his life, passing away there on June 8, 1902.