The "Winchester Mystery House" that Lorelai likens her home to is a mansion in San Jose, CA built by Sarah Winchester in the 1880s. It has over 160 rooms and is said to be haunted, and in fact originally built to house ghosts. Sarah supposedly thought she attracted the ghosts of dead family and could keep them happy by continually adding on to the home which contained haphazard and unplanned wings, stairways and hallways that ended abruptly, and doors that opened onto walls. The house is a tourist attraction today.
About 18 minutes into the episode Lorelai is speaking to Luke and she refers to her home as "The Winchester Mystery House". Jared Padalecki (Dean) would later go on to star in the television series Supernatural (2005), where he plays a character named Sam Winchester, who, coincidentally, has a brother named Dean.
First appearance of the second troubadour, played by Dave Allen. Allen would go on to portray the electrocuted ghost in the subway in Ghostbusters (2016), which starred Gilmore Girls alum Melissa McCarthy.