Built in the middle of the 17th Century, the Sir John Falstaff takes its name from Shakespeare's Henry  IV's friend and partner in crime at Gads Hill. There is evidence to suggest that the doctor's surgery next door was the original hostelry.

Charles Dickens described the Falstaff in the 'Uncommercial Traveller' as "...a little hostelry which no man possessed of a penny was ever known to pass in warm weather." Dickens was a frequent customer at the inn, using it to supply rooms for visitors when his own home Gads Hill Place, (located right across the road) was overflowing and to provide refreshments for the events he hosted.

Located on the old Dover Road about half way between Gravesend and Rochester, there was much trade brought by passing traffic and travellers. During the 19th Century, regiments often passed on their way to Gravesend where they embarked for India. Ship's companies who were paid off, rowdy and tipsy, often made the inn and the area very dangerous.

During that period, as with many village pubs, it became the mainstay of local social life. The Parish Council held their vestry meetings at the inn with the guardians of the North Aylesford Union met here to discuss the poor of the area.