Today’s guest is Perry Bliss of The Old Field Vineyards in Southold, a place that’s been farmed by her family for more than a century and has played an important role in the story of North Fork wine.

Perry grew up on this land, returned to it, and helped guide The Old Field through generations of change, from vegetables to vines, from family tradition to modern winemaking, all while staying deeply connected to the people and the place around her.

In this conversation, we talk about legacy, farming as a family, learning to embrace change, and what it means to be present for a place from start to finish. And toward the end, Perry shares openly about the difficult decision her family made to sell the property, and why, not as an ending, but as part of a much longer story.

Today I’m joined by Bob McInnis, who many of you know as the North Fork’s go-to marketing mind behind some of our most recognizable local businesses and organizations. Bob is the founder of McInnis Digital, where his team helps clients grow through smart websites, search and AI optimization, social media, email marketing, automation, and both print and digital advertising, along with photography and drone services.

We talk about his work with businesses and organizations like Southold Fish Market, Suffolk Security, Jernick Moving & Storage, North Fork Sanitation, the Shelter Island Chamber of Commerce, the Mattituck Park District, the Greenport Miniature Railroad, and many others. Bob reflects on what makes local organizations endure, and what it takes to stay strong as the North Fork continues to grow and change.

Bob and his wife became year-round Greenport residents in the mid-1990s, initially using it as a home base between international travel as speakers and consultants on local business growth. Over time, Bob made the decision to stay put, focus his expertise locally, and raise his three children through the Greenport public school system.

We also look back at Bob’s earlier years, from growing up outside Boston to attending Dartmouth College, where he led the Dartmouth Entrepreneurs group and helped found the National Association of Collegiate Entrepreneurs. Today, he’s a frequent guest lecturer at Hofstra’s Zarb School of Business and a longtime board member of the North Fork Chamber of Commerce, deeply invested in the future of this community.

https://www.mcinnisdigital.com/

https://www.facebook.com/profile.php?id=61585686402751

https://www.instagram.com/mcinnisdigital/

Today’s guest is Patricia Hammes, a Greenport resident who has played a central role in shaping conversations about growth, planning, and community life in the village.

Patricia brings a background that predates her time on the North Fork, and that broader experience has informed her work locally, most notably through her service as Chair of the Greenport Planning Board, where she has dedicated a great deal of time and service to the community.

In 2025, she also ran for the Greenport Village Board, coming just shy of a win and further solidifying her commitment to public service and civic engagement.

Today, we’ll talk about her path to Greenport, what drew her into local governance, how she thinks about balancing change with preservation, and her hopes for the village’s future.

Today, we’re joined once again by Michael Zweig to revisit a pivotal decade in the life of the North Fork, the ten-year struggle for its character and economic base, from 1985 to 1995.

Michael first visited the North Fork in the 1960s, returning more permanently in the 1980s, at a moment when the future of the region was very much an open question. Would the North Fork follow a path of planning, agriculture, and preservation, or be paved over by unchecked development? That tension between developers, environmentalists, and longtime residents shaped nearly every decision the town faced.

In this conversation, Michael reflects on his growing involvement in the community, from joining the Town of Southold’s Economic Advisory Committee in 1985, to helping examine the future of agriculture at a time when new forms of farming, including the emerging wine industry were beginning to redefine the land. He discusses grassroots organizing to protect open space, including the formation of Southold 2000, which later evolved into the North Fork Planning Conference.

We also talk about the political shakeup of the early 1990s, when dissatisfaction with both major parties led to the creation of United Southold, a new local political movement founded by Tom Wickham. Though short-lived, its 1993 victory reshaped the political dynamics of the town and left a lasting imprint on how Southold governs itself.

Along the way, Michael shares memories of Greenport during that era, his decision to join the Southold Fire Department, and how civic responsibility extended beyond meetings and policy. We close by turning to the present, the pressures facing the North Fork today, and Michael’s hopes for preserving the balance between community, environment, and economy in the years ahead.

Today I’m joined by Judy McCleery, photographer, writer, longtime community leader, and a lifelong North Forker whose story is deeply woven into the fabric of the East End.

Judy takes us back to her family’s arrival on the North Fork and her upbringing in Mattituck, sharing vivid memories of growing up here and how that sense of place shaped who she would become. From her years at Mattituck High School to early work in public service, we trace a path that reflects both curiosity and commitment to community.

Over the course of her career, Judy has worn many hats, recycling coordinator for the Town of Southampton, legislative aide in the early 1990s, bank employee in Greenport, a radio professional, and later a reporter and photographer, each chapter offering a different window into life on the North Fork and the people who make it run.

We also talk about her involvement in local politics, the East End Women’s Network, and her ongoing dedication to civic life, culminating in her current role as president of the North Fork Chamber of Commerce. Throughout the conversation, Judy reflects on why this place matters so deeply to her, and what she hopes the future holds for the North Fork and its community.

Today I’m joined by Gerald O’Hara, author of Breaking the Mauser Rifle. What began with a week spent with his grandparents in Ireland in 1985 grew into a thirty-year journey to record and preserve a family history shaped by the Irish War of Independence and the divisions of the Anglo-Irish Treaty.

Drawing on family memory, inherited stories, and recorded voices, Gerald traces not only his own family’s past, but a pivotal moment in Ireland’s story, one shaped by two grandfathers who stood on opposite sides of history.

In our conversation, we talk about turning oral memory into written history, blending family stories with archival research, the meaning behind the book’s title, and what it meant to bring the book home to Charlestown and share it with readers on both sides of the Atlantic.

Today I’m joined by Shawn Petretti, Superintendent of the Mattituck-Cutchogue Union Free School District. Shawn’s journey in education has taken him through nearly every level of school life, from teacher and dean to principal and now superintendent, giving him a leadership perspective shaped by years in classrooms and close connection with students and families.

We begin by talking about where Shawn grew up and what first drew him to education, then trace his path through the district and the experiences that continue to guide how he leads today. We also discuss what attracted him to Mattituck-Cutchogue, his early impressions of the district, and how its deep ties to local history, agriculture, and community influence the schools.

Along the way, Shawn shares stories that reflect the spirit of the district, including meaningful community partnerships and new initiatives. We wrap up by looking ahead, at the priorities, challenges, and moments that give him hope for the future of Mattituck-Cutchogue schools and the students they serve.

Today I’m joined by Faith Welch, a senior at Greenport High School, Student Council President, and youth historian whose work has earned national recognition, including the Princeton Prize in Race Relations.

Throughout high school, Faith has founded clubs, written articles, and conducted award-winning research exploring identity, local history, and what it means to grow up in Greenport. Her leadership and curiosity have made her a respected voice among her peers.

In our conversation, Faith reflects on her family’s roots in Greenport, the moments that shaped her childhood, and the early experiences that opened her eyes to questions of race, fairness, and community identity. She shares what has meant the most during her senior year, how her classmates view Greenport, and where she imagines herself a decade from now.