Esperanza and Irwin welcome Season 8 and 2026 with Steve Long, the East Hampton Historical Society's Executive Director, and Hugh King, East Hampton Village and Town Historian. With our celebration of America's 250th birthday, Steve and Hugh take a look back at American history through a local lens. We'll also hear all the Society's plans for celebration throughout the year.

Esperanza and Irwin have had Robin's Island on their radar for quite a while. But it took a request from Colin, one of our listeners, to make it happen. (Thanks Colin!). Located in the Town of Southold, between Little and Great Peconic Bays, the island can only be reached by private vessel. The history is fascinating, and there have been numerous owners over the years. We'll transport you back to a 1636 deed, and take it to present day, where it is owned and stewarded by Louis Moore Bacon. A fascinating, off radar story, and a meaty one at that.

Esperanza and Irwin have discussed Freetown, East Hampton previously. It has been a stand alone episode, and has come up often organically. This episode presents Freetown through the eyes of Freetown resident Kevin Scott. Kevin cares deeply about Freetown's past, and is outspoken in his concern for its future. At its core, Freetown is an American story, and as often is the case, it's abundantly clear so many aspects of American History come through when viewed through the lens of East Hampton itself.

Esperanza and Irwin return to their sweet spot: the 1970's. 50 years ago, in the Spring of 1975, the Rolling Stones were arguably the biggest rock band in the world; some would say they still are. But facing a variety of tax problems in the UK, the Stones recorded throughout Europe, in addition to LA. But there was a special lure to Montauk in 1975, where the locals gave them their space. The heart of this podcast is the Stones, but the star is Montauk, including the Shagwong, Eothen, Deep Hollow Ranch, and yes, the Memory Motel.

Esperanza and Irwin are joined by journalist, community organizer and Springs resident Biddle Duke. We learned a bit of Biddle's early life growing up as the son of a diplomat, living abroad, but always returning to Wyndecote, the family's summer home in Southampton. Wyndecote was also where Biddle's uncle, Tony Duke began developing the camp by loading a bunch of NYC kids he met on the streets to pitch tents on Wyndecote's lawn. From those modest roots, Boys Harbor was born. An enthralling story, told by a great storyteller. Listening is Believing.

The Long Island Railroad's “Cannon Ball” made its first trip to Montauk from Jamaica, NY in 1890, and operated until the 1970s. The continuous service was provided on weekday afternoons from Long Island City until 1951 when service was then provided from Penn Station. Originally, the Cannon Ball was a train composed entirely of parlor cars – the epitome of luxury – and many regarded the Cannon Ball as a prestigious way to arrive in the Hamptons. But the real conversation of the Cannonball starts with the history of the LI Rail Road. Most of the effort out here was in the 1890’s, and a lot of it grew out of one man’s dream, Austin Corbin, who was a very wealthy banker in New York. He became President of the Long Island Railroad in 1881. As soonas he got onto this job, he had a lot of problems because he inherited a railroad that was bankrupt and actually had been formerly three different railroads. Once he put those together after about a year or so, he turned to the fulfillment of his dream and that was, not necessarily to build a railroad to the end of Long Island. His objective was to shorten the distance by water, over the ocean, between England and New York.

Esperanza and Irwin welcome Sarah Kautz, the Executive Director of the Southampton History Museum. The question is an intriguing one: Did the Mayflower Pilgrims land at Conscience Point, Southampton as well as Plymouth Rock? Through a fun and free wheeling conversation, Sarah shares some thoughts and theories illuminating a fascinating part of American history, within the boundaries of eastern Long Island.

While Esperanza and Irwin both share their personal connections to the Art Barge, this extraordinary story speaks for itself. While Victor and Mabel's lives were devoted to Art, they couldn't have been more different. Victor was one of 11 children of Italian immigrants, Mabel an only child descending from the original settlers of our country. Victor created the education department at MOMA, while Mabel was the Art Department Chair at Rye High School. But it's their arrival to remote Lazy Point, Amagansett in the 1940's, and tugging a decommissioned naval vessel from Jersey City to the shores of Napeague Bay remains a source of wonder to this day.

Esperanza and Irwin go back to a far quieter Springs, September 1970. George Sid Miller's farm field became the launch site for a dream — and the scene of a tragedy. Three young adventurers set off in the Free Life, a hot air balloon bound for Europe, in a daring attempt to cross the Atlantic. But the balloon and its passengers vanished without a trace, leaving behind a mystery that still haunts the community today.

In this episode, we explore how the Free Life launch shook the close-knit Springs neighborhood that embraced it as its own, and the lingering questions asked for over 50 years. What drove the crew to take such a risk? And how did this brief moment in aviation history leave such a lasting impression. A story of youth, ambition, community, and loss — told from where it all began.

In this special episode, we sit down with Pulitzer Prize-winning architecture critic Paul Goldberger to revisit his seminal 1983 New York Times article, "The Strangling of a Resort." Over four decades later, we explore how his observations about overdevelopment, zoning failures, and the clash between preservation and profit still echo through the East End today. What has changed? What hasn't? And what does the future hold?

Join us as we reflect on the past, examine the present, and consider what it will take to preserve the character of eastern Long Island in the face of relentless growth.