Esperanza and Irwin discuss Freetown, East Hampton. Following the passage of the Gradual Emancipation Act of 1799 in New York State, John Lyon Gardiner and other wealthy local slave-owners settled newly freed slaves in Freetown. Some of these households bore the last names of their former owners in subsequent census records. Rufus Right, Cyrus Hedges, William Gardiner, and Luce Gardiner were early African American residents of Freetown. In 1879, a New York City real estate developer, Arthur W. Benson (Bensonhurst, Brooklyn), acquired 10,000 acres in Montauk, where a group of  Montaukett  people maintained a small community. Benson and local officials relocated the Montaukett households to Freetown, offering them cash and deeds to newly subdivided lots. Many direct connections to Freetown's past survive today. Archival records about the community of Freetown are preserved in East Hampton Library's extensive Long Island Collection. Moreover, a number buildings and sites survive. For example, the George and Sara Fowler House, and Saint Matthews Chapel.

Esperanza and Irwin start Season Five with Mayor Gary Vegliante of Westhampton Dunes. In the late 1980's, a severe coastal storm battered this then unincorporated section of Westhampton practically into oblivion. Homeowners lost access to their houses to the point of police barricades denying entry. Current Mayor Gary Vegliante was a teacher and restaurant owner, and along with other politically unconnected residents, fought not just "city hall", but the County, Town, State and Federal government, ultimately incorporating a Village, right down to paving the road themselves. An unbelievable, feel good story that you have to hear to believe.

Esperanza and Irwin welcome Columbia University Professor Alexander Stille, the author of The Sullivanians. The Sullivan Institute was a maverick psychoanalytic practice and cult that flourished on the Upper West Side from 1957 until 1991. Paramount to the Sullivanian doctrine was the rejection of the traditional nuclear family and monogamous relationships. “The Sullivanians told myparents that the worst thing a person can do is raise their own children,” said Lauren Olitski, the daughter of painter and patient Jules Olitski. The patients were high functioning, intelligent and creative people, including the singer Judy Collins and writer Richard Price. But its influence over Jackson Pollock, and its presence in the Barnes Landing section of Springs for a fascinating, and different, Our Hamptons Podcast.

Esperanza and Irwin hearken back to the days before 300 plus cable tv channels and numerous streaming options. If you're of a certain age, you remember channels 2 to 13, and possibly UHF. Rooftop antennas, tin foil on the rabbit ears. But eastern Long Island weren't getting TV out of NYC. Apparently, those signals did not travel effectively west to east. Rather, channels out of Hartford, New Haven and Providence were the only game in town, and not all to clear either. A fun look back at an era where technology certainly did not rule.

Esperanza and Irwin welcome the filmmaker Joanne Roberts to discuss The Bonackers Project. The loss of the commercial fishing industry on the east end has been well documented. Overreaching government intrusion, onerous regulations and a powerful sports fishing lobby, combined with ever increasing house prices damaged an industry whose legacy dates back hundreds of years. Joanne shares the stories, and the challenges the remaining fisherman and baymen face, and the timetable for the film's release.

Esperanza and Irwin discuss a time when unspoiled Lazy Point was an industrial zone unto itself, with multiple fish factories operating. They even had their own LIRR Train Station for the employees to arrive there from points west. It was seemingly the perfect place for an industry that generated some awful smells from the factories. But with its isolated location it really wasn't bothering anyone. Until it was.