Esperanza and Irwin both have a connection to Longhouse; Esperanza is Head of Education and Community Engagement while Irwin has been a Docent. Sure, Longhouse is a stunning physical property; 12 acres of gardens, pond, sculpture. But the true story of Longhouse is Jack Lenor Larsen, a 20th century visionary. Jack purchased the property, a former potato field of flat land completely overgrown with bramble, invasive plants and poison ivy. Jack's ability to conceptualize this transformation from a potato field is nothing short of extraordinary. A dunescape, created by re-using the soil dug for the foundation. A series of pathways of mystery, where you see the start, but not the finish. A series of structures, often built with things recycled from the property. Jack transformed the property much as he transformed the textile industry, with the ability to see things in three dimensions. We tried to provide insight into all things Longhouse, and Jack. But seeing is believing. Longhouse is worth a trip from anywhere.

In a captivating conversation with Charlie Tupper, member of the storied Tupper family, listeners are transported to Towd Point's rich past. Charlie recounts his grandfather's journey from Nova Scotia to Southampton, purchasing the summer home in the early 1900s. He shares anecdotes about the charming 'Ramblers Cottage', its unique features, and the development of the area. Stories of childhood summers and heartfelt reflections on family legacy illuminate the emotional ties to this historic land, making it clear why Towd Point holds such significance in the community.

Discover the early life of Jacqueline Bouvier Kennedy Onassis in East Hampton, her family's iconic estate 'Lasata', and their ties to the Southampton Hospital. Learn about the Bouvier family's integration into the East Hampton community, the impact of the 1929 stock market crash, and the rescue of their relatives from 'Grey Gardens'. Explore the luxurious lifestyle of the family, Jackie Kennedy's connection to East Hampton, and the profound legacy the area has on prominent figures.

Esperanza and Irwin look back on the way Real Estate was bought and sold on eastern Long Island, in the not too distant past. Before the internet, before Zillow, before Redfin, before Real Estate firms with national and world wide presence. As recently as the early 1970's, there were not many more realtors then in the early 1950's, and many were part timers. Sure, there was money to be made in the summer colonies, but those markets were dominated by Lyda Barclay in Southampton, and Condie "Boots" Lamb in East Hampton. But a couple of newcomers arrived, with very different styles and backgrounds. Allan M. Schneider and Tina Fredericks each found lane to make inroads in the eastern Long Island real estate industry, ultimately transforming it entirely.

Esperanza and Irwin reflect on Beach Hampton's history, from Richard B. Allen's land acquisition to the development of a middle-class community. They discuss architect Alfred Scheffer's designs, Barbour Beach Hampton Club, and anecdotes from residents. The podcast explores the evolution of Beach Hampton's architecture, affordable cottage designs, and reminiscence of past traditions in Amagansett.

Esperanza and Irwin welcome Brenda Sinclair, third generation Hampton Bays resident, and executive director of the HB Historical Society.   We admitted to being a bit mystified by this hamlet, and Brenda's hometown stories and memories brings it all together.   Brenda tells us about the storied history and many lives of the Canoe Place Inn, now in the process of being reinvented again.  

Esperanza and Irwin tell the story of East Hampton's grandest estate in the early 20th century. Frank Wiborg was a self made millionaire by age 40, establishing offices worldwide for the distribution of ink and lithograph products. Originally summer renters in Amagansett and East Hampton, Wiborg ultimately became a land baron, with holdings encompassing and astonishing 600 acres. In 1909, Wiborg hired the renowned architect Grosvernor Atterbury to design The Dunes, a 30 room stucco mansion that became the largest house in East Hampton. On the ocean, with stables, a dairy barn, sunken Italian gardens and servants quarters. But the grandeur of The Dunes was befallen by personal tragedy and illness, and didn't survive to see its 30th birthday.

Esperanza and Irwin explore Riverhead's changes when the Tanger Mall arrived in the 1990s.   Riverhead still lays claim as the Suffolk County Seat, despite most government departments moving to office space up island in Hauppague.   Did Tanger, and the subsequent onset of big box retailers and chain stores help to offset that loss at the expense of ushering in a more suburban rather than rural feel for the community?   For those on the North and South Fork's, the convenience of having these options within an hours drive was probably a benefit.   It also helped keep large scale retail development away from the South Fork in particular, a fear we touched on in our episode about Bridgehampton Commons.    But there were ramifications for Riverhead's historic downtown as well.    

Esperanza and Irwin look back at the three lives of Bayberry Land in Southampton.   In 1916, the banker Charles Sabin and his wife, Pauline Morton Smith Sabin purchased these 314 acres for a country home, naming it after the low growing shrub prevalent on the east end.   The estate comprised 8 buildings, including a manor house, garage with chauffer's apartment, gatehouse, caretakers cottage, hunting stable...you get the idea.   The Sabin's lifestyle was as grand as the setting, entertaining New York's Blue Book society, Southampton's summer colony, as well as senators, judges and members of congress.   Come 1949, the property was sold for $131,250 to the International Brotherhood of Electrical Workers Local 3.  The union president is a name familiar to anyone driving the Van Wyck Expressway, Harry Van Arsdale, Jr.  A convalescent rest home, an education center for its workers, as well as a children's camp were just some of the changes made during the Union's 50+ years of ownership.  In 2001, the IBEW sold the property for $46 million dollars to Michael Pascucci, who created a golf course on the property designed by Jack Nicklaus.    Purchasing it at auction for the same price, but unable to consummate the deal was a second buyer, Donald Trump.  Mr. Pascucci in his own words wanted people who were non glitzy, saying it wasn't a valet parking type of place.   Those people however, did have a $650,000 membership fee.

The podcast discusses the historical significance of Shelter Island, its evolution from a summer colony to present day, the revitalization of the Historical Society, and the use of art to showcase the island's history. Personal reflections and gratitude for preserving Shelter Island's culture are highlighted throughout.