In 1851, brothers Robert and Peter joined with James Robertson, brother-in-law of Peter, in forming McCracken & Robertson Brewery.  The brewery was located in Little Collins Street, close to Williams Street.  Robertson retired in 1861 selling his share of the business to brothers Robert and Peter.  In 1873, Robert Montgomerie was employed bringing brewing experience that enhanced sales and helped lead to the success of McCracken City Brewery.  The tied-house system, which involves the owning of pubs by a brewery and only allowing them to sell beer manufactured by that brewery; also contributed to the brewery’s success.  In 1888, the brewery fronted Collins Street covering almost four acres, and was one of the most successful in Melbourne.  In 1907, the brewery was sold and became part of Carlton United Breweries.

The McCracken’s are regarded as the founders of the Essendon Football Club.  The club was formed at a meeting at "Ailsa" in 1872.  Among the foundation members present were the McCrackens,  William S. Cox(owner of Moonee Valley Racecourse), woolbrokers R. Dalgety and A. Younghusband, Brigadier-General Fred G. Hughes, baker Robert Ovens, J. Forrester, E. Stephenson, John Peck, W. E. Filgate, C. Yuille and Edward Wright (first chairman of the borough of Essendon).   

The club’s home ground was on the south side of Kent Street behind “Ailsa”, known as McCracken’s Paddock.  Several members of the family were early club officials, and some played for the team.  Robert was the first club president, Alex the first secretary, and Coiler the club’s first captain.  Alex, Coiler, John and James McCracken also played for the team in its early years.  Alex went on to become club president in 1887 after his fathers’ death, and also the first president of the Victorian Football League.  He was elected the club’s first life member in 1905.  The McCracken’s were believed to have come up with the red and black colours for the team guernsey, and the name “Same Olds”, by which the team was known in its early years.   

Lack of transport in the area prompted the beginning of the railway to Essendon.  With support from established local dignitaries such as Hugh Glass and Edward Wright, Peter floated the Melbourne and Essendon Railway Company.  The inaugural train ride took place on October 22, 1860.  Fares at the time were fourpence per mile first-class, threepence per mile second-class.  Horses, cows and other large stock one shilling each per mile, smaller animals at half price.   

But problems arose which were to later lead to the closing of the line.  At the time Essendon was a predominantly residential area.  As such, commuters to the city only required transport in mornings and evenings, and the train would often return from Spencer Street with no passengers at all.  Trains would frequently break down and need to be removed for repair and in March 1863 there was a serious derailment.  It’s no surprise that passengers became apprehensive about rail travel. It was quite common for them to be greeted in the morning by a sign reading “Essendon line closed. Engine undergoing repairs.”   

In 1863, the line was offered for sale for £75,000 but the government was not interested.   By July of 1864 the line was officially closed.  The line was eventually sold for £22,500 in 1867, the company having no choice but to sell.  In January 1871, the line between Melbourne and Essendon was permanently reopened.  (See History of Broadmeadows line)

The McCracken family lost a great deal of money that was invested in the failed railway.  Due to huge personal losses Peter was forced to sell "Ardmillan House" and all land west of the railway.  He and his family relocated to the Eastern suburbs.  

In November 1910, Coiler and Alex sold 3 acres of land in Buckley Street to the Minister of Public Instruction for £1,000.  Essendon High School was later erected on the site.  When the land was purchased “part of the agreement with the vendors was that they would name the road on the east side of the property – McCracken St.”