The first bicycle race on the Isle of Man was at Quarter Bridge in the grounds of Kirby House, the home of Deemster Drinkwater. Deemster is an IoM term for judge and at this time the Deemsters served on the IoM legislature. Sir William Drinkwater was the First Deemster from 1855 until 1897. He bought Kirby House in 1840 and was keen on sports.
The Isle of Man Times on 17th July 1869 reports on the Athletic Festival held on 14th July "in the field, opposite the Quarter Bridge, forming a portion of the estate surrounding Deemster Drinkwater's beautiful residence of Kirby". A crowd of two to three thousand people attended the event which included three bicycle races. The first was a slow bicycle race, the next a one mile scratch race. Interestingly JC Radcliffe who won the scratch race, challenged the second place rider "for any sum from £5 to £50, to run a bicycle race from Douglas to Laxey". The final event was a road race around Quarter Bridge of about 1¼ miles.
After the success of this meeting, a second Athletics Festival took place on August 4th 1869 at Kirby in aid of the Isle of Man hospital. The prizes of cups and medals were valued at £50 and a crowd of 6,000 people watched the events. As well as the running races there was a one mile bicycle race, which attracted only three entries. It was thought that "bicyclists seem to have an objection to competing in a field, and preferring the highway." Amazingly, for an event held on private land, bookmakers were present and drew the wrath of the press. The Isle of Man Times of August 28th 1869 commented "There were many unfair and suspicious interferences with runners - one especially being worthy of notice, in the shape of a betting man running up to Kenyon, and shouting to him to lose the mile race".
A further festival at Kirby was the last of the year and was held on September 20th 1869. The meeting included a quarter mile bicycle race with seven entries. The event raised about £20 for the hospital.
There do not seem to have been any more sports held at Kirby House or grounds after these three 1869 events.