Dive into the scandalous legacy of Millicent Rogers, a high-society icon from a wealthy but tumultuous family. Discover the extravagant 'Port of Missing Men' and its notorious reputation during the Roaring Twenties. Uncover the architectural influence of John Russell Pope and the Olmsteds on Eastern Long Island. Explore how Prohibition changed social dynamics for the elite, illustrating their indulgent lifestyles. Millicent's adventurous spirit and resilient character shine through her complicated life, leaving a lasting legacy in a world of riches and mystery.

Dive into the storied past of Ocean Castle, where opulence met scandal! Discover how bootlegging fueled extravagant lifestyles and led to wild parties that wreaked havoc on the property. Hear about the notorious gatherings that resulted in chaos, including a dramatic night featuring 1600 broken windows. This captivating journey through Southampton's high society reveals a mix of architectural ambition and tragic tales, showcasing the excesses and darker sides of wealth.

Glenn Navia and Stacey Testa, creative minds behind Cedar Cottage Springs, discuss their journey from corporate careers to running a community-focused Airbnb in the Hamptons. They share insights on the evolving rental landscape and the balance between hospitality and community connection. Listeners learn about their unique approach to hosting, emphasizing warmth and personal touches. The couple reflects on the challenges posed by short-term rentals and the importance of maintaining local relationships amidst a rapidly changing environment.

The podcast dives into a nostalgic look at the Hamptons, highlighting a 2006 article that captures the vibrant artistic past of the area. Listeners explore shifting community dynamics shaped by wealth and development, reflecting on friendships forged among artists. Stories of local bars and baseball lore offer a glimpse into cultural traditions, while discussions on preservation illuminate community engagement. The speakers express gratitude for their surroundings and the wisdom gained, reminding us of the enduring connections amid ongoing change.

Discover the intriguing history of the Devon Colony, founded by Cincinnati families in 1908, blending Mediterranean architecture with coastal charm. Learn about the legacy of unique traditions, like cannon shooting at sundown, which enrich the Amagansett community. Dive into the importance of preserving the area's untouched beauty and historic buildings, ensuring that its quaint character remains intact for future generations. Uncover the stories behind the founding families and their connection to the Devon Yacht Club.

Bess Rattray, a columnist for The East Hampton Star and founder of the Anchor Society, shares her insights on preserving her hometown's charm. She reflects on the quirks of growing up in a newspaper family and the challenges of local journalism. Bess discusses the Anchor Society's mission to bring a General Store to East Hampton, addressing issues like 'luxury blight.' The conversation also highlights ways to revitalize the community through partnerships and innovative projects, advocating for a balance between luxury and local character.

Esperanza and Irwin leave their usual comfort zone and head into more uncharted territory. Calverton has the last, large swath of Long Island grassland, and has been protected to a degree. If you visit the area, there doesn't seem to be much development or planning, although proposals exist. It's home to an enormous FedEx distribution center, a large recycling business, along with tiny farmhouses and farms. We''ll tie in the Calverton Executive Airport, the Grumman Corporation's impact on LI, and its Memorial Park on 10 adjacent acres.

Geoff Gehman, author of "The Kingdom of the Kid: Growing Up in the Long Lost Hamptons," shares heartfelt tales from his childhood in Wainscott during the 1960s. He vividly recounts adventures like crabbing and camping, revealing the emotional ties that draw him back to his hometown. The conversation delves into the area's rich cultural heritage, the enchantment of its natural beauty, and the lasting impact of community initiatives. Gehman also reflects on the significance of local landmarks and the essence of Wainscott that continues to inspire creatives.

Esperanza, who has firsthand experience with one-room schoolhouses, and Irwin, an expert on their evolution, discuss the surprising number still standing in Eastern Long Island. They explore fascinating transformations—some have become community centers or luxury homes. Esperanza shares her insights as a parent with children in a one-room setting, highlighting the benefits of multi-age classrooms. Their conversation uncovers the historical significance of these structures and their enduring role in local identity.

Maryann Calendrille and Kathryn Szoka, proprietors of the beloved Canio's bookstore in Sag Harbor, share their journey of preserving a cultural landmark. They discuss the origins of Canio's and its evolution into a community hub since its 1999 acquisition. With the impending loss of their lease, they express hopes for a new chapter, emphasizing the importance of independent bookstores in fostering community connections. Nostalgic tales of Sag Harbor's past merge with a vision for Canio's future, keeping the spirit of literature alive.