Miniature whaleboats have been a hallmark of HarborFest in Sag Harbor going back to the 1960s, when author John Steinbeck and others founded the annual event, originally known as the Old Whalers Festival. The whaleboats went under a long-overdue restoration this year to keep them afloat for many HarborFests to come. HarborFest Whaleboat Committee leader Gavin Menu, who is also a co-publisher of The Express News Group, joins the editors on 27Speaks this week to talk about the history of whaleboat racing at HarborFest, which returns September 14 and 15.

A replica of the Amistad docked in Montauk in August, during the same week in 1839 when the original Amistad came aground at Culloden Point in Montauk. The schooner became famous after the Mende people onboard, who had been abducted in Africa to be sold into slavery, revolted against their captors. The ship was seized, and the Mende were put on trial in Connecticut for mutiny. Ultimately, the court sided with the Mende and defended their actions to secure their freedom. Brenda Simmons, the executive director of the Southampton African American Museum, Mia Certic, the executive director of the Montauk Historical Society, and Paula Mann-Agnew, the executive director of Discovering Amistad, join the editors on the podcast to discuss the significance of the Amistad and the planning that went into bringing the replica to Montauk for the first time.

The Express News Group and WLIW-FM are collaborating on separate, issues-based interviews with incumbent Republican U.S. Representative Nick LaLota and Democratic challenger John Avlon. The interviews serve as a way to drill down on topics of importance to the East End and the entire 1st Congressional District and get the candidates on the record about their plans and positions. Diane Masciale, the vice president and general manager of WLIW21 and WLIW-FM, and Gavin Menu, a co-publisher of The Express News Group, join the editors on the podcast this week to discuss the project.

Express News Group interns Hope Hamilton and Dan Stark join the editors to discuss their experience this summer.

Hamptons Collegiate Baseball League President Sandi Kruel and Tom Gleeson, the league's director of development, join the editors on 27Speaks to discuss HCBL's history and the current season.

When Aby Rosen, a billionaire real estate mogul, and his son, Charlie, decided to add the Southampton Village movie theater to their extensive portfolio of properties, they weren’t seeing dollar signs. Instead, they say, they were drawn to the historic but rundown theater — which went dark and has stayed that way since the start of the pandemic — for more personal reasons. During a recent exclusive tour of the theater, reporter Cailin Riley learned about the Rosens' vision for the Hill Street theater, which was originally built in 1932, and purchased by them for $8 million in late 2022. This week Riley joins the editors to share what she’s learned about what’s next for the theater.

East Hampton Town is considering a proposal for the site of the former Stern’s department store to be redeveloped with 48 one-, two- and three-bedroom apartments, which will then be sold to local employers to house their employees. Kirby Marcantonio, the publisher of Montauk Life and Hamptons Life magazines, and a group of investors is pitching the novel solution to East Hampton’s workforce housing crisis. Reporter Christopher Walsh joins the editors on the podcast to discuss these plans and other affordable housing solutions.

Roundabouts and other measures to help move traffic along are being explored at difficult intersections and chronically backed-up roads across the South Fork. Reporters Stephen Kotz and Michael Wright join the editors on the podcast this week to discuss specific proposals.

East Hampton Village recently banned late-night restaurant clubs and prohibited all restaurants in the historic districts from staying open past 11:30 p.m. The village's moves were designed to head off rumored plans to turn the Hedges Inn into an exclusive club akin to Manhattan's Zero Bond. Reporter Christopher Walsh, who has written on the topic, joins the editors on the podcast to discuss.

Father Alexander Karloutsos, the protopresbyter of the Dormition of the Virgin Mary Greek Orthodox Church of the Hamptons and the Greek Orthodox Archdiocese's representative to the White House, joins the editors on the podcast to discuss his relationship with President Joe Biden and past presidents going back to Jimmy Carter. In 2022, Biden presented Father Alex with the Presidential Medal of Freedom, the United States' highest civilian award.