Following the Pledge of Allegiance at the top of last Tuesday’s Southold Town Board meeting , Supervisor Al Krupski asked all in attendance to remain standing for an invocation. At the invitation of Councilman Greg Doroski, the Rev. Sean Norris of Dandelion Ministries in Cutchogue spoke to a room of bowed heads.

“Almighty God, our heavenly father, send down on those who hold public office — especially each member of this Southold Town Council — the spirit of wisdom, of charity and of justice, that with steadfast purpose they may faithfully serve in their offices to promote the wellbeing of all people,” the Rev. Norris said. Residents who frequently attend or tune in to Town Board meetings will note that he is the fourth religious leader this year to kick off a Town Board meeting with a prayer. That’s because doing so before one meeting each month is a custom Mr. Krupski brought with him from the Suffolk County Legislature. 

“Working in Hauppauge all those years, before every general meeting, somebody would bring clergy right after the pledge to just give us a few words of encouragement,” Mr. Krupski said after last week’s meeting, which also marked his 100th day in office. “So once a month, and we will rotate through the different board members, someone will bring clergy in to give us a few words … It’s a nice way of being mindful that we live in a pretty diverse community, especially religious-wise, so we’ll try to have a diverse cross section of clergy come in.”

After a decade serving at the county level, Mr. Krupski has returned to Town Hall this year for the first time since 2013. Election certificates chronicling his political career — which he began as a Town Trustee (1986-2005), then Town Board member (2006-13), county legislator (2013-23) and now supervisor — hang on the freshly painted walls of his Town Hall office.

“I’ve never worked in this office before, but it was an easy transition from the meeting room,” Mr. Krupski said. “I’ve seen a lot of supervisors come through here … I want to try to contribute my knowledge, my efforts to make this town better for the next generation. This is a good town. One of the most encouraging [reasons to run for supervisor] was all the people who work here and the people who live in town who want to volunteer their time [on] the committees.”

A few weeks after his victory over Republican supervisor candidate Don Grim, Mr. Krupski, who was endorsed by both the local Democratic and Conservative parties, began making the rounds at Town Hall and the annex, meeting with department heads and volunteers who serve on the committees and task forces that tackle issues ranging from battery storage facilities to deer management. In addition to the legislative and public-facing duties, Mr. Krupski’s position as supervisor, which earns him $126,963 annually, per the town’s 2024 budget, requires him to manage town finances and serve as its emergency preparedness coordinator. 

When asked about the proudest accomplishment of his first 100 days in office, the supervisor pointed to his focus on resident safety. Highway Superintendent Dan Goodwin and town engineer Michael Collins have been tasked with developing a map identifying the town’s most flood-prone streets in order to outline clear evacuation routes during storms and extreme high tides. Mr. Krupski hopes this project will be completed by year’s end.

He added that he and other members of his emergency team met with local fire chiefs to discuss the difficulties their departments’ volunteers face when responding to calls under such conditions.

“The outreach to the community, I think, is going to pay off,” he said. “I’ve always been a part of the East End Supervisors and Mayors Association meetings as a county legislator, so I know it’s very good to have that line of communication with your different partners in government.”

Among nearly a dozen major concerns Mr. Krupski mentioned, he highlighted Southold’s persistent housing crisis and pointed to a March 26 Town Board vote to close loopholes in town code that allow developers to skirt certain affordable housing requirements.

“That was something done because you don’t want to miss an opportunity to build affordable housing,” Mr. Krupski said. “We’re never going to build enough housing for all the people who work in town. We’ll make an effort there, but I could be here for 20 years and I don’t think that will ever end.”

Mr. Krupski’s North Fork roots, firmly planted on his family farm in Peconic, are clearly displayed on his desk at Town Hall. A case houses a trio of model train cars, one of which bears the logo of the North Fork Potato Chip company, a logo originally designed by Mr. Krupski’s great-grandfather, Martin Sidor, for his farm’s burlap potato sacks.

A fourth-generation farmer, the supervisor works his family business alongside his wife, Mary, and their children, Nick and Kim. “I’m the one who gets the tractors ready, greases them up, changes the oil and makes sure the plow parts are all done,” he explained. “All winter I kind of have a schedule.” 

After six weekends of coordinating and waiting for calm weather, Mr. Krupski and his family recently replaced the plastic roof on their 125-foot-long greenhouse. He said he rises each morning and tends to the tomatoes, peppers and eggplants inside, and that he recently planted some peas, “just a few rows,” for his eight grandchildren to pick.

Mr. Krupski’s predecessor, Scott Russell, prided himself on being accessible to the public and hosted regular evening office hours, when constituents were free to discuss any issue they wished. The new supervisor does not have regularly scheduled office hours, but said he may offer them “at some point.” For now, he and his secretaries, Lauren Standish and Michelle Tomaszewski, both of whom worked with Mr. Russell for many years schedule in-person appointments. 

Mr. Krupski credits his deputy supervisor and longtime legislative aide, John Stype, for suggesting he furnish his office with a round table to meet with residents at Town Hall.

“I think it’s been most encouraging to see the community engagement,” he said. “I think it’s good for people to understand how government works, and also the limits of government. The more they’re engaged, the better it is.”