Hales Wilkie was born at Tunbridge Wells, Kent on the 27th January 1837.  Son of Emily and Mary Wilkie. His father was the Magistrate Deputy Lupt (Ramsgate, Kent).

Hales was Educated at Oxford. He purchased a commissioned in to the 97th Foot (The Earl of Ulster's) as Ensign on the 18th August 1854. He was promoted to the rank of Lieutenant on the 3rd January 1855. Served with the 97th Foot in Crimea from the 16th June 1855, including the siege and fall of Sebastopol (Medal with Clasp, and Turkish Medal). 

Attained the rank of Captain by purchase on the 24th July 1857 still serving with the 97th Foot.

He served in the Indian campaign of 1857-58, and was present with the Jounpore Field Force in the actions of Chanda, Umeerpore, and Sultanpore, and afterwards at the siege and capture of Lucknow (Medal with Clasp).

On the 18th March 1859 he exchange from the 97th Foot to the 29th Foot. Attained the rank of Major by purchase on the 20th February 1863 still serving with the 29th Foot (Worcestershire). On the 31st October 1871 Major Hales Wilkie was appointed to command the 29th Foot (Worcestershire) Regiment with the rank of Lieut.-Colonel by purchase. He handed over command to Lieut.-Colonel Howell Davis on the 2nd March 1878.
Lieut.-Colonel Hales Wilkie, having completed his qualifying service in command of the 29th Foot (Worcestershire), was given the rank of Brevet Colonel on the 31st October 1876 and went on the officers reserve list on half pay.

On the 2nd March 1878 he transferred from half pay to served as a staff officers to command a Brigade Depot with the rank of Lieut.-Colonel. He continued in this role until the end of 1881.

As a staff officer with the Regimental District, Lieut.-Colonel and Brevet Colonel Hales Wilkie, was appointed Assistant-Adjutant and Quartermaster-General, Northern District, on the 21st December 1881. On the 18th April 1885 he was appointed to be Deputy-Adjutant and Quartermaster-General.

On the 27th March 1886 he was promoted to the rank of Major-General and moved to Malta still in the position of Deputy-Adjutant and Quartermaster-General.

In 1887 he commanded the Frontier Field Force in Egypt and on the 1st January 1888 moved back to Valletta, Malta to command an Infantry Brigade, with the rank of Major-General. He held this position for the next few years.
 

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