As far as can be established the Bailie Bar, or the site of the Bailie Bar, has been a bar since the 1870's, in its previous incarnation it was known as the Grand Bar. The Grand bar was very much a working man's "Spit and Sawdust" bar, as were the majority of bars in Stockbridge. It was also quite different in design to what the Bailie Bar is now. There was no restaurant area as during that period no food would have been served. There was also a small "Snug" bar, commonly known as the Jug bar which was where women were allowed to drink! However there were no female toilets in the bar!

In 1971 the Grand Bar was bought by Hamish Henderson, some of whose artwork can still be viewed in the Bailie, and it was Hamish who renamed the pub the Bailie, apparently after a theatre production that was on at the time. The advert for the production is still in the Bailie to this day. At this time there was no restaurant area. During this period Stockbridge was very different to what it is today. St. Stephen Street was very dilapidated and there were plans to basically knock the street down and build anew. This caused outrage with the many antique dealers and small businesses in the street that legend has it stopped this.

During the early 1980's the Bailie Bar's current owners bought the pub from Hamish and made some substantial changes to it. The beer cellar was moved from the inside to the outside of the bar into the previously unused cellars underneath the pavement. The bar was more than doubled in size by buying the adjoining 2 basement properties. This extension now forms the restaurant and dining area, kitchen and toilets. This time including a ladies toilet! The old gent's toilet handle still exists in the place of the original toilet. However this can often cause confusion for our older regulars who have had one to many!

Other than a few minor changes to the pub - adding televisions (one of which is hidden in the wall behind a picture, try and find it!), some improvements to the exterior to accommodate the smoking ban in 2006 and basic running repairs the Bailie Bar is the same today as it always was. There is no music, no fruit machines and no juke box. Banter and debate are encouraged around the large island bar and to this day many regulars still exist who first started drinking here in the 1950's and 1960's. Some of them are featured in a famous photograph on the wall of the Bailie. This was taken in 1973 and shows the bohemian characters who frequented the pub during the late 1960's and 1970's.