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.

Esperanza and Irwin welcome Glenn and Stacey, the proprietors of Cedar Cottage Springs. Like many places, Eastern Long Island rentals have dramatically changed. Seasonal rentals, have shifted from the previous Memorial Day to Labor Day season to shorter term rentals; often very short. Airbnb's dominate, and are the source of much displeasure. But for Glenn and Stacey, they are not renting their house, they are sharing their HOME. Two creative types, they've brought a warmth and quirkiness to a business that often lacks exactly that. They are immersed in our community, and our conversation takes in that, and much more.

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.

Dr. Susan Van Scoy, a professor at St. Joseph's University and author on the duck farming industry, shares fascinating insights into the history of duck farming on Long Island. At its peak in the 1950s, 75% of the nation's restaurant ducks came from this region. She discusses the challenges faced by local farmers, including suburbanization and government regulations, which led to the decline of the industry. The iconic Big Duck also features prominently as a symbol of this rich, yet often overlooked, heritage.