If you've ever tried to walk from the Wainscott Village Center to Wainscott Green, you already know the problem. The sidewalk gets you partway there, ends at the HomeGoods store, and leaves you to finish the trip on the shoulder of Montauk Highway with cars moving well past a walking pace. Locals have been pointing this out to the town for seven years. The gap is still there.
That's not a complaint about slow bureaucracy. It's a window into something more interesting: why a hamlet built around a strip of small businesses along Montauk Highway still can't get a continuous sidewalk built, even after the town wrote the plan, put a price tag on it, and got residents to agree on where to start.
A Strip, Not a Street
Wainscott doesn't have a Main Street in the way East Hampton or Amagansett do. It never did. What it has is Montauk Highway, and for decades that stretch has carried restaurants, antiques dealers, a golf course, real estate and insurance offices, car dealers, and everything in between, mostly clustered on the north side.
The middle of that run is the Wainscott Village Center, the shingled cluster across from the Wainscott Post Office. It's home to Panda Garden, one of the center's original tenants dating to the late 1980s, and the Wainscott Country Deli, run by the Baugh family, who also own the Sagg Main Store in Sagaponack. Breadzilla sits nearby. A few doors down, Wainscott Main Wine & Spirits has started running a Wine Wednesday series with Nick & Toni's, pairing guided tastings with small bites from the restaurant's kitchen, a small but telling sign that the corridor's businesses are starting to lean on each other for foot traffic rather than just competing for it.
That's the texture of the place today. What's changed less is the pavement between those businesses.
The Sidewalk That Was Supposed to Happen First
In 2019, East Hampton Town adopted a hamlet study for Wainscott into its comprehensive plan. The study didn't propose anything radical. It called for buried power lines, street trees, and a continuous sidewalk along the business district, the same basic ingredients that make a stretch of road feel like a place you'd walk rather than a place you'd drive through as fast as possible.
By 2022, a working group had actually agreed on a starting point. The estimate for replacing about 1,120 linear feet of cracked, non-compliant sidewalk, roughly a third of the commercial core, came to $190,000. Carolyn Logan Gluck, who chairs the Wainscott Citizens Advisory Committee, argued for tackling the project in smaller pieces rather than waiting on a master plan, and pointed to extending the sidewalk from HomeGoods to Wainscott Green as exactly the kind of small, achievable win that would build momentum. Business owner Pat Trunzo, at that same round of meetings, described the hamlet's commercial strip as "'60s-style strip development."
It didn't happen that year. By 2024, consultants were back in front of the town board recommending the same basic streetscape work, this time along a defined 4,000-foot stretch from West Gate Road to Hedges Lane, with a cost estimate of $2.5 to $3 million just to bury the utility lines that would make the sidewalks and trees possible. Logan Gluck was back too, this time calling it the "SAT approach": do the easy questions first, then circle back to the hard ones, urging the board to "go for the low hanging fruit." Trunzo, at the same meeting, said before anything else happened, the state Department of Transportation needed to survey the highway to figure out if sidewalks were even physically possible along the whole stretch.
The Real Obstacle Isn't Money
Here's the part that doesn't show up in a quick drive-by of the hamlet. The sidewalk delay was never really about the $190,000, or even the $3 million. It's tangled up with a much larger, much slower fight over a 70-acre former sand mine sitting just north of the Speedway station, at what the town itself has called the "Gateway to East Hampton."
That parcel, known to the planning board as the Wainscott Commercial Center, has been under review since 2018. The current owner wants to subdivide it into 50 commercial lots. The town's own 2019 hamlet plan envisioned something different: more than half the site as public park, with a smaller portion for housing and a multi-use trail. Neither vision has won out. A 2023 public hearing drew more than 50 speakers and 150 comments, nearly all critical of the subdivision plan, and the project has been sent back for supplemental environmental review more than once since.
Logan Gluck put the connection plainly at a 2022 planning meeting: "I don't see how we can think about how the business district in Wainscott is going to take shape until we have answers about those two elephants in the room," referring to the sand pit and the future of East Hampton Airport, which also sits in Wainscott and was facing its own restrictions around the same time. In other words, the sidewalk plan and the sand pit fight aren't two separate stories. They're the same story, and the sand pit is the reason the sidewalk keeps getting pushed to "next year."
What Doesn't Change Is the Buildings. What Does Is Who's In Them.
While the infrastructure argument has stayed frozen, the businesses along the strip keep turning over, sometimes more than once in the same building. The Tudor-style house on Georgica Pond that anchors the east end of the corridor has cycled through several identities over the years, including a stint as Sapore di Mare, before becoming Il Mulino, the well-known New York group's Hamptons outpost. The building didn't move. The name on the door did, more than once.
That's worth sitting with if you live here. The corridor's physical bones, the highway, the curb cuts, the lack of a continuous sidewalk, are the most stable thing about Wainscott's business strip. The tenants are the part that keeps changing. It's a small irony that a hamlet without a fixed Main Street identity has, if anything, more restaurant and retail churn than its neighbors with an actual Main Street.
Where You Can Actually Walk Right Now
Until the larger questions get resolved, the practical reality for anyone walking this stretch is uneven. The Wainscott Village Center itself is a self-contained, handicapped-accessible pocket, with ample parking and a short connecting walkway between its buildings, so once you're parked there, getting between the deli, the wine shop, and the restaurant is easy. The trouble starts when you try to connect that pocket to the next one down the highway. The HomeGoods-to-Wainscott Green gap that Logan Gluck flagged back in 2022 is still the clearest example: a resident on foot has to choose between the shoulder of a state highway or driving the quarter mile instead.
None of this means the hamlet lacks activity. Wine Wednesdays keep filling a Wednesday night, and the deli built its business on the early commuter crowd. But the walkable version of Wainscott that the 2019 plan promised, tree-lined, connected, a place you'd choose to stroll rather than just pass through, is still mostly a rendering in a town planning document, waiting on a decision about a sand pit that has now outlasted two full town boards.
If you're weighing what daily life actually looks like in a hamlet like this, that gap between the plan and the pavement is exactly the kind of detail worth knowing before you assume the brochure version is the real one. For a closer look at how Wainscott and the rest of the eastern South Fork are actually functioning day to day, from what's opening to what's stalled, Jennifer C. Wilson covers it weekly in the Monday Morning Matters brief. It's the kind of detail that doesn't show up on a listing sheet, but shapes what living here is actually like.
