The building that houses the Chequers started life as a private home in the 13th century. In the 15th century it became the premises of a money-lender and the checkerboard sign commonly used to advertise a money-lending business was retained in the pub sign when it became a hostelry in the early 16th century.

The pub took a turn for the weird in April 1762 when it became home to Oxford's first zoo. For a time it housed an eclectic menagerie of animals that Jackson's Oxford Journal lists as including 'a Sea-Monster from Siberia, supposed to be a Sea-Lioness; a Male Dromedary from Deserts of Arabia; an Opussum from America, esteemed the most extraordinary Animal in Nature, a Coatamunday from Brazil; and many other equally curious, the whole Collection being Fourteen in Number.'

Others accounts add to this list 'a very large fish, possibly a shark'! The logistics involved in transporting these to Oxford in the 18th century boggle the mind!

The Chequers seems to have been no stranger to putting on unusual attractions and side-shows. In April 1758 Jackson's Oxford Journal reported that for the price of one shilling the public could view what appears to be conjoined twins that were recently born in Witney. These are described (in rather superfluous detail) as 'having but one Head, yet two Faces, four Eyes, two Noses, four Cheeks, two Ears, two Chins, two Backs, four Arms, four Hands, twenty Fingers, four Thighs, four Legs, four Feet, and twenty Toes; these all complete and perfect.' This was described by 'a Gentleman skilled in anatomy' to be 'the greatest curiosity of its kind that ever yet appeared in Europe'.

In his book Curious Oxfordshire, Roger Long also makes a passing reference to the Chequers being at one point home to 'a giant' who was 'popular with students and graced many a dinner table'. This is perhaps John Middleton of Hale, a man reportedly over 9 feet tall who is known to have visited nearby Brasenose College and have had his portrait painted in the early 17th century.

According to the legend, there is a secret underground tunnel from the cellars of the Chequers to the Mitre public house that stands 50 metres or so away on the other side of the High Street. This was supposedly constructed during the Reformation to allow Catholics a way of escape if agents of Henry VIII came calling.

However, when Henry VIII's agents were finally tipped off about the escape tunnel, it became a tomb for one unfortunate group of monks. Henry's agents sealed up both ends of the tunnel with the monks inside and left them to starve or suffocate to death.

It is said that the chanting of the entombed monks can sometimes be heard in the cellars of both the Chequers and the Mitre.