As befits a place that’s offered regular ferry service from Long Island proper since 1846, Shelter Island has a particularly intimate relationship with its two cross-Sound conveyances. There’s the North Ferry, which runs from Greenport to Shelter’s North Shore, and the South, which travels from North Haven in Sag Harbor to Shelter’s south shore. The ferries are run by different companies, cost different amounts and travel different distances — 1.
1 miles for North, 0.4 miles for South. Still, nothing’s more different about them than the visitors they transport to Shelter and the expectations they lug with them.
Seen in the most reductive of terms, South Ferry types go looking for Hamptonsy things, while Northies gravitate toward the Greenporty and Mattituckish. Both groups tend to find just what they’re looking for, exactly what you’d expect from an island that the Manhanset Indians named Manhansack-aha-quash-awamock, which translates to "island sheltered by islands." But while Shelter shelters both sets of expectations, the best trips to the island are those that embrace both.
Or so we’re trying to prove during the following slapdash, possibly ill-advised itinerary, one which deliberately pingpongs back and forth between North and South Forkish sensibilities over the course of one long, very long Shelter Saturday. A view of Shelter Island from the North Ferry. Credit: Randee Daddona The first — and last — decision to make is yours: which ferry to take, o.