Greenwich
Greenwich has been the commuter town for New York money since the railway arrived in 1848, and in the 1990s it became the address of the hedge fund industry — several hundred funds operate from a town of sixty thousand, in office buildings that look like houses. Back-country estates sit behind stone walls on twenty-acre lots, ten minutes from a shoreline of yacht clubs and a main street of galleries.
Why go
The hedge fund capital — several hundred funds in a town of sixty thousand. Estates in the back country — stone walls, twenty-acre lots and roads with no through traffic. A working waterfront — yacht clubs, islands in the Sound and a public beach residents fought over. New York in forty minutes — the reason it exists at all.
The character
Greenwich became New York's commuter town when the railway arrived in 1848, and the pattern has held for 175 years: money made in the city, spent on land in Connecticut. The Gilded Age brought estates to the back country north of the Merritt Parkway; the postwar decades brought corporate headquarters; and from the 1990s the hedge fund industry arrived, drawn by Connecticut's tax treatment and a forty-minute commute, until several hundred funds were operating from converted houses and low office buildings around the station.
The town splits geographically by function. Greenwich Avenue is a shopping street with galleries and restaurants; the waterfront has yacht clubs, Greenwich Point and the islands; and the back country is estates behind stone walls, some on twenty acres, where the roads have no pavements and the horses have right of way. A famous 2001 court case forced the town to open its beach to non-residents, which locals still discuss. It is an unusually complete picture of American wealth: old money, corporate money and fund money layered in one municipality.
Places of character
Greenwich Point (Tod's Point) — the public beach and peninsula, with Long Island Sound and the New York skyline visible on clear days. Bruce Museum — art and natural history in a nineteenth-century stone house, better than a town this size should have. Greenwich Avenue — the shopping street, with the police officers who still direct traffic by hand at the crossings. Back country roads — Round Hill, Lake Avenue, John Street; stone walls, horse crossings and no pavements. Audubon Greenwich — nearly three hundred acres of woodland sanctuary in the north of the town. Cos Cob and Old Greenwich — the village centres where the town is less about money and more about living.
The way to do it
Drive the back country roads and then walk Greenwich Point — the two halves of the town are unrecognisable to each other. Take the train from Grand Central rather than driving in. And eat in Cos Cob or Old Greenwich in place of on the Avenue, where the prices are New York's.
One perfect day
Train from Grand Central in forty minutes, then coffee and Greenwich Avenue while the shops are opening. An hour at the Bruce Museum. Drive or cycle north into the back country: stone walls, horse farms, and the Merritt Parkway's 1930s bridges, each one different. Lunch in a village centre. Afternoon at Greenwich Point — the walk around the peninsula takes an hour and the Manhattan skyline appears at the far end. Late afternoon at the Audubon sanctuary or a yacht club terrace. Dinner in Old Greenwich, and the train back.
Grand hotels
Delamar Greenwich Harbor — on the water by the marina, the town's own hotel. J House — a converted motel in Riverside, quietly the better room and half the fuss.
When to go
Best expression: September and October, when New England colour arrives and the Sound is still warm. Consider: May, when the back country is green and the sailing season opens. Avoid if possible: midwinter, when the town is beautiful but everything happens indoors.
The frame
Ideal stay 1–2 nights, or a day from New York · Minimum a day trip · Best arrival Metro-North from Grand Central, 40 minutes · Airport JFK 60 km, LGA 50 km · Walkability the avenue and the point; the back country needs a car · Best without a car partly