The Hamilton Herald Newspaper and cigar store owner "Billy" Carroll, originated and sponsored the first "Around the Bay Road Race", run on Christmas Day, 1894. It is now the oldest road race in North America, older than the Boston Marathon which was born three years after the Around the Bay Road Race. The race tested the abilities of the finest long distance runners, but was also an avenue to lay down some bets.

The Around the Bay Road Race established Hamilton as a running mecca for long distance runners, and it was not uncommon for thousands of spectators to line the route to watch their local favourites start the race from the front of the Herald Newspaper Offices at 17 King Street West Hamilton.
Jack Caffery

In the early 1900's, Jack Caffery and William Sherring battled it out and won two "Bay" races each. Caffery went on to stun the Americans at the Boston Marathon in 1900, by being the first Canadian to win Boston.

To add insult to injury, Hamilton's William Sherring and Fred Hughson placed second and third, behind Caffery, making it a Canadian sweep. Caffery rubbed it in even further by coming back the next year 1901, to win Boston again.

Not to be outdone by Caffery, William Sherring went on to win the 1906 Olympic Marathon in Athens, Greece, making him a Canadian hero.
Tommy Longboat

That same year, Tommy Longboat, an Onondaga from Six Nations near Caledonia, won the "Bay" race and the next year in 1907, surprised everyone by winning the Boston Marathon. Hamilton's James Duffy

This information from Around the Bay Race Website. For more information go to bayrace.com