The postcard record

A Cove in Postcards

For sixty years, visitors to Greenport mailed pictures of this one small cove to the people they loved. Here is the collection — and what it proves: the boats were always here. Click any card to enlarge it.

1900s–1910s

The Hand-Colored Years

Printed in Germany and hand-tinted, these are the oldest views of the cove — the sailing era’s last decade. One in this collection was postmarked at Greenport on August 15, 1908.

Hand-colored postcard: sailboat and skiffs at Widow's Hole, circa 1910 — c. 1908–1913 — The classic view: a catboat off the beach, skiffs in the grass, the harbor’s masts beyond. Boats on stakes, a bulkheaded shore — already a boating place.

Hand-colored postcard: Shorefront, Widow's Hole with large shingled houses — postmarked 1908 — “Shorefront, Widow’s Hole.” The grand shingled houses above the bulkhead, a rowboat lying off — the shore already engineered for boats.

Ornate-bordered postcard: Shore Front, Widow's Hole with sailboat — postmarked 1908 — “Shore Front, Widow’s Hole,” in a printer’s ornamental border — a sloop ghosting past the houses.

Hand-colored postcard: Widows Hole with houses and many boats hauled on shore — c. 1910s — Boats of every size hauled along the shore below the houses. Note the big catboats — serious sailing craft, kept right here.

Postcard: Brennan's Landing, Greenport, a boat livery on the waterfront — c. 1910s–1920s — “Brennan’s Landing,” one of the Greenport waterfront’s boat landings — the age when every neighborhood kept its own fleet.

1920s–1940s

The Motorboat Years

Gasoline changes the fleet: cabin launches and cruisers take the stakes, and the publishers keep printing. Backs in this collection are postmarked 1923, 1937, 1938 and 1942.

Postcard: Yacht Racing in Greenport Harbor seen over the stone jetty — postmarked 1938 — “Yacht Racing in Greenport Harbor.” The race viewed from the cove — across the stones at its mouth, with a launch lying inside. The jetty has recently been restored to its prior proportions — see the jetty page.

Postcard: a fleet of motorboats moored and hauled at Widow's Hole — 1920s–1940s — The Hole at capacity: cruisers on moorings, skiffs on the beach, dinghies everywhere between.

Postcard: cabin launches lying to their stakes at Widow's Hole — 1920s–1940s — Workboat-style cabin launches lying to their stakes in the quiet water behind the point.

Postcard: Widow's Hole shoreline with launches along the bulkhead — c. 1910s–1930s — Launches along the bulkheaded shore below the big houses — the neighborhood’s front yard was a harbor.

Postcard: Shorefront Widow's Hole in black and white — c. 1910s–1930s — The “Shorefront” view in its black-and-white printing.

1950s–1960s

Boating Paradise, in Color

Kodachrome arrives at the cove. The backs of these cards did the bragging for Greenport: “Boating Paradise … Seagoing craft of all types can be found in this deepwater anchorage, which is a favorite rendezvous for visiting mariners.”

1950s color postcard: large cabin cruisers moored at Widow's Hole — 1950s — The deepwater anchorage earning its postcard-back boast — a raft of big cruisers and workboats inside the spit, the Shelter Island ferry crossing beyond.

1950s color postcard: a large cruiser moored off the old captain's house at Widow's Hole in winter — 1950s — A cruiser wintering off the point, below the old captain’s house where the widow’s story began.

1950s color postcard: sloop and red skiffs at Widow's Hole — 1950s — *Look how large this craft is — at what is now the Osinskis’!* This 50-foot Chris-Craft, owned by a local businessman, was kept at the present-day Osinski property — part of the cove’s long history of large-vessel navigation. Red skiffs on the bank; Kodachrome by Milt Price of Northport.

Messages home

“I like the sea life all right”

Turn the cards over and the cove speaks. A few of the backs in this collection, with their postmarks and their news:

Postcard back postmarked Greenport, August 15, 1908 — Aug 15, 1908 — “Hello Ida… I am all right and I like the sea life all right. — Frank.” Mailed from Greenport to Town of Union, N.J.

Postcard back postmarked Greenport, July 8, 1913 — Jul 8, 1913 — “Thought I would write a few lines & tell you what a nice place we have… I think you will like it & the people are lovely.” To Passaic, N.J.

Postcard back from the 1950s describing Widow's Hole as a sheltered deepwater anchorage — 1950s — The printed back that says it all: a “sheltered deepwater anchorage… a favorite mooring spot for local mariners.” Handwritten: “Here we are safe and sound… weather fishing is good.”

About the collection: these postcards are from a private Greenport collection and are reproduced here for their historical value. Dates given are postmarks where known, otherwise estimates from publisher and printing style. Corrections welcome.

“The Widow’s Hole, Greenport, L.I.” — hand-colored, c. 1908–1913

“Shorefront, Widow’s Hole” — hand-colored, postmarked 1908

“Shore Front, Widow’s Hole” — postmarked 1908

“Widows Hole, Greenport, L.I.” — c. 1910s

“Yacht Racing in Greenport Harbor” — postmarked 1938

“Brennan’s Landing, Greenport” — c. 1910s–1920s

“The Widow’s Hole” — 1920s–1940s

“Widow’s Hole, Greenport, Long Island”

“Shorefront, Widow’s Hole” — black-and-white printing

“The Widow’s Hole — Boating Paradise” — 1950s

A cruiser wintering off the point — 1950s

A 50-foot Chris-Craft at the present-day Osinski property — Kodachrome by Milt Price, 1950s

Postmarked Greenport, August 15, 1908

Postmarked Greenport, July 8, 1913

Printed back, Tomlin Art Co. — 1950s