Jim Davidson, founder of the Hampton Jitney, originally set out to address the transportation gap during the 1974 gas crisis. He shares how a simple idea evolved into a crucial service linking Manhattan and the Hamptons. The conversation touches on the community spirit fostered by the Jitney, its unique branding by Roy Lichtenstein, and the transformation from small vans to larger coaches. Davidson reflects on the nostalgic ties between the Jitney and local culture, celebrating its 50-year journey of connecting people across the East End.

Esperanza and Irwin welcome Susan Horowitz, of Hamptons 20th Century Modern. Susan formulates advocacy efforts to both raise awareness and influence actual preservation efforts by viewing modernism as a continuum of the architectural history of eastern Long Island. While Long Island modern architectural history is documented by writers such as Paul Goldberger, Alastair Gordon + Caroline Rob Zaleski, Long Island continues to face crucial need to focus on the legacy of the modern architects and their architecture, before they are forgotten and their work is demolished. While much has already been lost, part of Hamptons 20th Century Modern's mission is to encourage owners of these homes to protect their futures, and new buyers to consider them as valuable historic homes. We also discuss how eastern Long Island relates to other US areas of successful modernism preservation across the country; New Canaan, Palm Springs and Cape Cod. Watch for Hamptons 20th Century Modern's upcoming House Tour, scheduled for August 11 and 12.

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.

Discussion on the history and preservation of Montauk's Seven Sisters, designed by famous architects. Focus on the unique design challenges and financial struggles faced by the families living in these iconic properties. Explore the reconstruction efforts of a summer cottage after a fire to maintain authenticity. Mention of listener suggestions for future episodes, including a possible Freetown episode.

Author Alexander Stille discusses The Sullivanians cult, rejecting traditional family structures and influencing prominent figures like Judy Collins. The podcast explores the fine line between therapy and exploitation, unraveling the downfall of the group in the 1980s.

Larry Rivers, a prominent artist known for his public art installations, discusses the controversy and impact of his 16 foot tall 'Legs' sculpture in Sag Harbor. The podcast explores the clash between government decisions and the artistic community, balancing historic preservation with artistic expression. It also delves into the history of public art in the community and the challenges it faces.

Explore the vibrant disco era in the Hamptons, reminiscing about iconic clubs like Mellow Mouth and Martell's Oceans. Reflect on the evolution of nightlife culture, tragic events, and shifting celebrity dynamics. Learn about the transformation of Grumman Airplane Factory into a legendary music venue, Bay Street, hosting stars like Billy Joel and Tina Turner. Dive into the history of East End discos, from glamour to retail office spaces, and reflect on the fading disco culture.

The podcast explores the vibrant social scene at Asparagus Beach in the 1970s where singles mingled. It discusses traditional dating norms, fashion trends, beach culture, group rentals, and LGBTQ+ history in the Hamptons. Nostalgic reflections on past beach experiences and casual encounters are also highlighted.

Esperanza and Irwin take a nostalgic trip back to the 1970s, reminiscing about the limited television options on East End. They share amusing tales of rooftop antennas, tin foil, and battling reception issues. The conversation highlights how scarce media choices fostered tight-knit community gatherings. They also reflect on television's role as a social hub and delve into historical events, intertwining local culture with memories of early cable TV. It's a fun exploration of simpler times before today's media overload!