William Matthews was granted a publican's license for the St. John's Tavern at Darlington in June 1838, 1839 and 1840.
The licence was transferred from William Matthews to Edward Greenland in April 1841. Edward Greenland had previously held the license for the Wheatsheaf Inn at Hexham.
In December 1841 - 'that well known house, situated at Darlington, Patrick Plains and possessing every convenience for carrying on a first rate trade in the public line' was advertised to be let. Immediate possession offered.
Edward Greenland was granted the license for St. John's Tavern again in June 1842 
James Doyle held the license in June 1843 and 1844.
In June 1845 Walter Rotton was granted the license. In 1846 Michael McCann who was employed as an out door servant by Walter Rotton was sentenced to hard labour for six weeks after he stole a pint pot of brandy from the tap at the hotel. Walter Rotton had left his brother John Rotton in charge of the Inn in his absence and McCann had taken the opportunity to steal the brandy.
John Singleton was the next innkeeper having been granted a license in June 1847.
Injured policeman Sergeant Edwards was taken to the inn in April where he was treated by Dr. Glennie.
John Singleton's wife gave birth to a daughter at Darlington in September 1847 while they were still at the Inn.
Bourn Russell Junior
According to the Maitland Mercury, Bourn Russell junior who married a daughter of Benjamin Singleton, was granted a licence for the St. John's Tavern in April 1848 .
In June he held the licence for the Prince of Wales at Stoney Creek, Jerry's Plains. Bourn Russell junior left for the California gold fields in 1849 
The Inn was known as the Prince of Wales Inn in 1849 when James Briggs became publican....... 'A pigeon match and race for a saddle will take place at the Prince of Wales Inn, Darlington on St. Patrick's Day. The pigeon match to be for a pony, entrance for which will be in all Four Pounds; and the saddle of best quality to be run for by all horses except those known on the turf. James Briggs over the river from Singleton'. 
James Briggs had two charges brought against him under the Licensing Act. In October 1850, he was charged with failing to keep good order in his house by allowing a certain woman to be improperly dealt with. The evidence of constable Joseph Davis (which could not be published) was that he found women drinking and making a noise in Mr. Brigg's house and knowing one of these women to be a woman of loose character, who had recently left the gaol, he cautioned Mr. Briggs as to allowing her to be on his premises. The following afternoon Davis returned to the house, and again in the evening, and on both occasions he found this woman there, very drunk and he described what he observed, and what passed. The bench convicted Briggs, reminding him that this was the second conviction against his house. He was fined £10 and costs. (It was possibly this James Briggs who arrived as a convict on the Speke in 1821. He was assigned to John Bull in 1828 and received a ticket of leave for the district of Patrick Plains in January of that year although it was later cancelled for disorderly conduct.)
In October 1849 Robert Hardy obtained a certificate for a publican's general license for the Prince of Wales Inn and renamed it the Freemason's Arms.
 Hunter River Gazette 18 December 1841
 Certificates for publicans' licenses, 1853-1861. NRS 14403, reels 5063-5066, 1236-1242. State Records Authority of New South Wales