The first Canadian Masonic Lodge meeting was held at what is now the Sinclair Inn in 1738. On November 14, 1737, Major Erasmus James Philipps and William Shireff were initiated into the "First Lodge" of Boston, Massachusetts, Both were members of the Governing Council of Nova Scotia under Lieut. Governor Armstrong, and were in Boston as Commissioners to settle the boundaries of Massachusetts and Rhode Island. In the Boston Gazette of March 13, 1738, we find the following paragraph;

"We are inform'd, That Major Philipps is Appointed Provincial Grand Master over the Free and Accepted Masons, in the Province of Nova Scotia, and that a Deputation is getting ready for that purpose."

Despite the fact that there is some indication that a Masonic Lodge existed in Annapolis Royal in the years 1721-23. (See Beginnings of Freemasonry by M. M. Johnson p. 51, 81), sometime in the latter half of 1738, Major Philipps established, with the assistance of William Shireff, what was the first Freemason's Lodge in Canada. When Philipps visited the Lodge in Boston in April, 1739, he was referred to as "Grand Master of Nova Scotia". R.V. Harris, Masonic historian also says:

"On returning to Annapolis in June 1738, Philipps took with him a deputation from Henry Price to form a lodge at Annapolis Royal with himself designated as the first Master. The record reads that Mr. Price granted a Deputation at Ye Petition of Sundry Brethren at Annapolis in Nova Scotia to hold a Lodge there. This Petition was undoubtedly signed not only by Philipps and Shirreff, but also by Col. Otho Hamilton and Dr. Wm. Skene, both Masons and residents of Annapolis Royal for many years. The lodge established in 1738 was the first lodge established in what is now the Dominion of Canada, and was the fifth in order of precedence of lodges chartered from Massachusetts."

Harris also has this to say about William Skene: "DR. WILLIAM SKENE, a member of the Aberdeen family prominent in the records of the Aberdeen Lodge of Aberdeen No. 1 there, was attached to the garrison at Annapolis as surgeon, as early as 1715. He became a member of the Council in 1720, and, along with John Adams and Shirreff, was a member of the first Court of Justice in 1727."

And, also:

"Three other members of the Lodge whose names have come down to us are John Easson "made" in 1738; Isaac DeCoster, later the first Master of St. Andrew's Lodge, Boston, also "made" in 1738, and Francis Barclay LeCain "made" in 1751; all Master Artificers in the employ of the Board of Ordnance."

The Lodge at Annapolis Royal was the fifth in order of precedence of Lodges chartered by St John's Grand Lodge of Massachusetts. It was called the Annapolis Royal Lodge and Erasmus James Philipps was its first Worshipful Master. There is no indication that this Lodge lasted beyond 1767, and it is not until 1795 that Grand Lodge #25 was established. Frederick Sinclair was an innkeeper, and it was in "his large room below stairs" that meetings of the Annapolis Royal Lodge #25 were held, as well as sessions of the Supreme and Inferior Courts. Sinclair is noted as "PM" in this Lodge, which indicates that he had previously been a "Worshipful Master". It is possible that Frederick Sinclair had been a member of the first Annapolis Royal Lodge since he arrived in the area sometime before 1770.