In this episode, Stars Hollow is holding a dance marathon to raise money. Dance marathons began in the 1920s and were at their peak in the 1930s, with people vying to win the cash prize at the end, that could be for as much as a year’s salary. Today they are generally held as charity fundraisers, and only last for twelve to twenty-four hours, not the thousands of hours they went on for in times past, which sounds like absolute torture (and they were often rigged as well).
We learn that the dance marathon is an annual event, that Lorelai has been close to winning it for four years in a row, since 1998, and that the previous year she only lost at the eleventh hour. It’s possible the one in 2001 took place around the same time as Mia’s visit (she may have come back for it). The one in 2000 presumably took place after Lorelai’s date with Max.
According to the banner in the town square, this is the 50th annual dance marathon in Stars Hollow, so the first one was held in 1952. In fact, this is around the time dance marathons began to decline in popularity. Could Stars Hollow have really been thirty years behind the trends?