At a lively session of the Southold Economic Development Committee’s summer “Synergy Summit” last week, local leaders, entrepreneurs and civic stakeholders zeroed in on concrete proposals to reverse youth flight, stimulate economic growth and unify the community stakeholders’ fragmented efforts under a single digital platform.
The dominant themes were strikingly consistent across breakout tables: create a shared community calendar, confront the town’s housing affordability crisis with urgency and better coordinate events, resources and communication across business and civic organizations.
“We operate in silos,” said committee member Jennifer Wheeler Del Vaglio, summarizing her group’s discussion. “The fire departments, the educational components, the civics, the business community — we don’t seem to interact as much as we should.”
A unifying website
Several attendees returned repeatedly to the need for a central, non-governmental website to act as both a community hub and a tourism driver. “The website [would handle] not most, but a big chunk of everything that was listed here,” said Amanda Guiliano, a business owner and group facilitator. “Where to shop, where to stay, where to play, where to learn.”
Paul Romanelli, who led the morning’s wrap-up session, underscored the importance of creating “solid, web-based tourism type, strong messaging that we can get out” — something akin to websites that Asheville, N.C., and Hudson, N.Y. have used to boost local economies.
Participants envisioned a platform that would host a master calendar, business directory, housing resources, relocation information, job listings and shared promotional campaigns. Attendee Richard Vandenburgh suggested that funding could come from a hotel tax.
“You pay it when you travel,” he said. “Why not here?”
Tiny homes and youth flight
As the conversation turned to youth retention, Jack Malley didn’t mince words. “The average age in probably most of these fire departments is 60 plus,” he said. “We need small houses so these young folks can live.”
George Cork Maul agreed.
“Try putting up a 750-square-foot house in the Town of Southold,” he said. “All the houses that were 1,500 or 2,000 square feet are turning into part-time houses where nobody comes out except for three weeks and the sprinkler runs all day.”
Vandenburgh suggested a potential workaround — stylish, affordable tiny homes already in use at a local campground. “Base cost is about $40,000 to $50,000,” he said. “Beautiful kitchen, beautiful bathroom… it doesn’t look like a trailer at all.”
Rosemary Winters of the Cutchogue-New Suffolk library suggested another approach: incentives for homeowners to purchase tiny homes as rentals.
“I have a couple of staff members who live with their parents right now, and there’s no apartments here,” she said. “One of them just got an apartment in Sound Beach. Now she’s going to have to drive an hour every day.”
Guiliano and others suggested a voucher system to help local workers bridge the affordability gap.
“If a house out here… was $4,000, and she could afford $2,500,” she said, “the town could help bridge the gap with what she actually could afford through a voucher.”

Zoning and incentives
EDC committee member Elizabeth Sakarellos and Town Councilwoman Anne Smith reported recent policy changes to support accessory dwelling units (ADUs) and a new full-time housing development supervisor.
“The town is trying to help,” Sakarellos said, noting multiple ADUs already approved in Mattituck and Southold.
Smith added that “the subsidies right now going to developers can be a range of market price versus affordable, and you would get subsidies based on the percentage … And the next level of subsidies that we’re fleshing out will be to people who are trying to buy a home, rent a home, employers who are trying to attract employees — maybe helping with like first and last month’s rent, different grants.
“If you stay a certain amount of time, you don’t pay it back. If you leave, you pay it back. But now we have someone who can actually monitor that and make sure all those things are happening and that permits are being issued,” she said of the new housing development.
Maul remained skeptical. “They’re not making it easier for people to live together — they’re making it harder,” he said. “They have too many [regulations]. They’re not there yet.”
The economic fallout of Southold’s demographic shift was made painfully clear by several business owners.
“There is just not enough youth out here now,” Guiliano said. “I cannot hire a manager. I can afford to pay $40,000 a year … but no hits and a lot of no shows.”
Romanelli said part of the solution may be to reinvigorate “anchors and destinations that people will want to come to and young people want to be involved in.” He contrasted Greenport with Westhampton Beach. “I was there two weekends ago on a Sunday night — mobbed. Absolutely packed with people walking around stores, open restaurants, entertainment. People want to be able they have to have things to do when they get here.”
‘Support each other’
To tie it all together, several speakers called for a centralized board or committee to oversee the proposed website and serve as a bridge between organizations.
“We need to present this to the [Southold Town] Board,” Malley said. “Make a solid combined group… ‘We need your help. We need your funding.’”
Wheeler Del Vaglio suggested that email chains and shared calendars were good interim tools but not enough. “These kinds of things need to happen on a regular basis, not just haphazardly,” she said.
Guiliano proposed a Google Sheet calendar shared among local groups. “Just go on and start plugging in your events,” she said.
The session closed with an appeal to keep momentum going. “A simple idea we talked about [in a breakout group] — support each other,” Malley said. “Somebody’s having a problem? Hey, that could be on the email thread. ‘Can you help me?’”
From tiny homes to website overhauls to youth housing vouchers, one message rang clear: Southold’s EDC believes that the business community’s future will depend on breaking down silos and working more closely together.
