In 1828, the Pennsylvania Legislature authorized the construction of the railroad between Philadelphia and Pittsburgh. This was known as the "Main Line" of the Public Works system and is the reason this area of Philadelphia is called the "Main Line".

Realizing the potential of the "Main Line", the state of Pennsylvania purchased the land surrounding the new railroad stations to create "summer homes" for the Philadelphia Elite. To ensure the success in Bryn Mawr, the State prohibited the building of "hotels, taverns, and drinking saloons, or other buildings of offensive occupation".

Legend has it that the first establishment to become approved was right at this spot. The "Ivy Inn" opened at this location to provide food and spirits worthy of Philadelphia's finest. Unfortunately, prohibition brought an end to the success of the Ivy Inn.

Fortunately, Mrs. Kelly, who changed the name to Kelly's, reopened it. Mrs. Kelly ran Kelly's as a family business until the late 60s. After her retirement, several different groups owned Kelly's, including a group of Villanova professors, a local Bryn Mawr businessman, and others. During these many transitions, Kelly's started to show its age.

An attempt to renovate the building was made, but multiple hurricanes destroyed its progress, forcing construction to stop and Kelly's to close in 1998. It was in the year 2002 that a group purchased the building and started construction on their dream of returning Kelly's to its former reputation as a place for family, friends and neighbors to gather for good food and good times.