It has been criticized because of its image as a stereotypical "smoke-filled room" where lobby groups gain access to government officials, a few of whom have been known to use taxpayer funds to pay their way to New York. Other observers criticize the retreat for being held in New York instead of within Pennsylvania.
The tradition for Pennsylvania's political and business retreat dates to 1899, when James Barr Ferree, a native Pennsylvanian living in New York invited a group of 55 other Pennsylvanians living in New York to the Waldorf-Astoria Hotel to discuss current affairs in their native state. The dinner became a recurring event and the group began calling themselves "The Pennsylvania Society of New York." It later developed into an annual gathering of Pennsylvania politicians and businessmen on New York's "neutral ground." The organization later changed its name to The Pennsylvania Society and became a nonprofit charitable organization. It was incorporated in 1903, and currently claims 2,000 members. While it sponsors a high school essay contest, the main function of the organization is to organize the weekend retreat.
The gathering began as an exclusively Republican event, but it now includes a sizable number of Democrats. The early years of the meeting were reminiscent of the stereotypical smoke-filled room, where Pennsylvania steel, coal and oil magnates met in closed-door meetings to select their political candidates. That public perception continues, with political legend telling of New York-based businessmen summoning Pennsylvania's politicians to New York to receive their instructions for the following year.
The main attraction of the weekend is the "Pennsylvania Society Dinner," a black tie event held in the Waldorf-Astoria Hotel on the final night of the weekend. In 2005, about 1,500 individuals attended. However, much of the "real action" takes place in the invitation-only dinners and receptions hosted by businesses, candidates, and lobbying firms throughout the weekend. In an attempt to attract more attendees, hosts have hired top tier guests, including Jon Stewart, Lewis Black, and George H.W. Bush, who ended his 2003 speech with a reference to Dana Carvey's impression of him by saying, "Not gonna do it. Wouldn't be prudent." Several events have become well known for drawing high-powered guests, including the events hosted by the Pennsylvania Manufacturers' Association. In 2004, an evening at an Upper East Side cigar lounge hosted by Republican national committeewoman Christine Toretti Olson gained significant praise from attendees. In a 2005 event, Rick Santorum was able to raise $46,000 for his 2006 re-election campaign and $130,000 for the Pennsylvania Republican Party.
The Pennsylvania Society has become known as the "unofficial start of the next year's big political season" because of its reputation as a place for potential political candidates to make contacts, meet fundraisers, and make a name for themselves early in the electoral process.