To describe the inn as "the first house in Southwark" might have
been accurate for those callers who approached it over London
Bridge, but in actual chronology the proud distinction of dating
from post-deluge days has really to give place to the much more
recent year of 1319. There is, preserved among the archives of the
city of London a tavern lease of that date which belongs without
doubt to the history of this hostelry, for it refers to the inn
which Thomas Drinkwater had "recently built at the head of London
Bridge." This Thomas Drinkwater was a taverner of London, and the
document in question sets forth how he had granted the lease of the
Bear to one James Beauflur, who agrees to purchase all his wines
from the inappropriately named Drinkwater, who, on his part, was to
furnish his tenant with such necessaries as silver mugs, wooden
hanaps, curtains, cloths and other articles.

A century and a half later the inn figures in the accounts of Sir
John Howard, that warlike "Jacke of Norfolk" who became the first
Duke of Norfolk in the Howard family and fatally attested his
loyalty to his king on Bosworth Field. From that time onward casual
references to the Bear are numerous. It was probably the best-known
inn of Southwark, for its enviable position at the foot of London
Bridge made it conspicuous to all entering or leaving the city. Its
attractions were enhanced by the fact that archery could be
practised in its grounds, and that within those same grounds was the
Thames-side landing stage from whence the tilt-boats started for
Greenwich and Gravesend. It was the opportunity for shooting at the
target which helped to lure Sir John Howard to the Bear, but as he
sampled the wine of the inn before testing his skill as a marksman,
he found himself the poorer by the twenty-pence with which he had
backed his own prowess. Under date 1633 there is an interesting