Old Shelter Island Postcards

This arbor denoted the entrance to The Heights from what is now Bridge Street.
The "Shelter Island", oil by Antonio Jacobsen (1850-1921) Built in 1886, the "Shelter Island" was one of two craft owned by the Montauk Steamboat Company which ran from Sag Harbor to Shelter Island, Southold, Orient and New York, accommodating as many as 250 passengers in 50 staterooms. The painting is owned by and is on display at the Oysterponds Historical Society Museum in Orient.
Another version of the same scene as above. In color, the bridge is better defined.
It is hard to imagine such a huge ediface sitting on the area which is now a park across from the tennis courts in the Heights. It poured down the hill toward the beach club which is merely a shadow of the bathing pavillion that once stood in its place.
This is probably a scene from the dock of the Bathing Pavillion at the New Prospect Hotel.

South Ferry from Shelter Island to North Haven.

North Ferry from Greenport to Shelter Island.

Boats at the pier at the Yacht Club.

The Chequit Inn in The Heights.

Greenport Railroad Station and Ferry Slip


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