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What to See in Shelter Island - Top Sights and Attractions

Discover 10 hidden attractions, cool sights, and unusual things to do in Shelter Island (United States). Don't miss out on these must-see attractions: Fire Fighter, Greenport, and Havens House. Also, be sure to include Brecknock Hall in your itinerary.

Below, you can find the list of the most amazing places you should visit in Shelter Island (New York).

Fire Fighter

Museum in Greenport, New York
wikipedia / Dmadeo / CC BY-SA 4.0

Museum in Greenport, New York. Fire Fighter is a fireboat which served the New York City Fire Department from 1938 through 2010, serving with Marine Companies 1, 8 and 9 during her career. The most powerful diesel-electric fireboat in terms of pumping capacity when built in 1938, Fire Fighter fought more than 50 major fires during her career, including fires aboard the SS Normandie in 1942 and the SS El Estero in 1944, the 1973 collision of the Esso Brussels and SS Sea Witch, and the terrorist attacks on September 11, 2001.[1]

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Greenport

Village on Long Island, New York
wikipedia / CGP Grey / CC BY 2.0

Village on Long Island, New York. Greenport is a village in Suffolk County, New York, United States. It is on the north fork of Long Island. The population was 2,197 at the 2010 census.

The village of Greenport is within the town of Southold and is the only incorporated community in the town.

Greenport was a major port for its area, having developed a strong fishing and whaling industry in the past, although currently there are only a handful of commercial fishing vessels operating out of Greenport. More recently the tourism industry has grown substantially too, especially in the summer.[2]

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Havens House

Building
wikipedia / Americasroof / CC BY-SA 3.0

Building. James Havens Homestead is a historic home located at Shelter Island in Suffolk County, New York. The house was built in 1743 and expanded in the early- mid-19th century. It is a large wood-frame building with wood-shingle sheathing, broad gable roof, wraparound porch, and rear wings. The main section includes a two-story, three-bay side-entrance-hall dwelling which was enlarged to four bays with a wide two-story, one-bay addition. Also on the property is a small wood-frame shed.

It was added to the National Register of Historic Places in 1986.

The house is owned by the Shelter Island Historical Society and operated as a historic house museum.[3]

Address: 16 S Ferry Rd, 11964 Shelter Island

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Brecknock Hall

Event venue in Greenport West, New York
wikipedia / Darshanbib / CC BY-SA 4.0

Event venue in Greenport West, New York. Brecknock Hall is a historic home located at Stirling in Suffolk County, New York. It was built in 1857 and is a 2+1⁄2-story, square cut ashlar stone residence in the Italianate style. The central projecting gable has a one-room sized cupola centrally located on the roof. Also on the property is a 19th-century barn, a small early 20th-century greenhouse, and an early 20th-century caretaker's house.

It was added to the National Register of Historic Places in 2005.[4]

Address: 31 Sandpiper Lane, Shelter Island (Northfork)

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Manhanset Chapel

Chapel in Shelter Island
wikipedia / Americasroof / CC BY-SA 3.0

Chapel in Shelter Island. Manhanset Chapel, also known as Mechanics' Hall, is a historic nondenominational chapel at 24 N. Ferry Road in Shelter Island, Suffolk County, New York. It was built in 1890 and moved to its present site in 1924. It was originally located on the grounds of the Manhaset House Hotel. It is a modest, frame Gothic Revival style structure. It consists of a gabled nave; a prominent, square engaged tower; a distinct chancel with a lower gabled roof; and a rear entrance wing.

It was added to the National Register of Historic Places in 1997.

In 1986, the Osofsky family donated the chapel to the Shelter Island Historical Society, which restored it to the 1924 period of its significance when it was used by the Junior Order of United American Mechanics. In 2011, Randy Osofsky repurchased the chapel with her husband, Stephen Kessler, for use as an arts and events space for Shelter Island.[5]

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Shelter Island Windmill

Shelter Island Windmill
wikipedia / Americasroof / CC BY-SA 3.0

Shelter Island Windmill is an historic windmill north of Manwaring Road in Shelter Island, Suffolk County, New York. It was built in 1810. The windmill has been on Shelter Island since 1840, in its current location in 1926, and has been on the Sylvester Manor farm ever since.

It was added to the National Register of Historic Places in 1978.[6]

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Smith-Taylor Cabin

Smith-Taylor Cabin
wikipedia / Americasroof / CC BY-SA 3.0

Smith-Taylor Cabin is an historic Adirondack style log cabin located in Coecles Harbor on Taylor's Island at Shelter Island in Suffolk County, New York. The original cabin was built around 1900 by Francis Marion Smith of "20 Mule Team Borax" fame. In 1937 S. Gregory Taylor added a bedroom, bathroom, kitchen, foyer, and landmark tower with catwalk.

It was added to the New York State and National Register of Historic Places in 2007.[7]

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Sylvester Manor

Sylvester Manor
wikipedia / DanTD / CC BY-SA 4.0

Sylvester Manor is a historic manor on Shelter Island in Suffolk County, New York, USA.[8]

Address: 80 N Ferry Rd, Shelter Island

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Shelter Island Country Club

Golf club in Shelter Island Heights, New York
wikipedia / DanTD / CC BY-SA 4.0

Golf club in Shelter Island Heights, New York. Shelter Island Country Club is a historic country club located at Shelter Island in Suffolk County, New York. The club was established in 1901 and consists of a nine-hole golf course, club house, driving range, and maintenance facility. The club house is a two-story Colonial Revival-style wood-frame building with a side-gabled gambrel roof with five dormer windows on both the east and west elevations. It features a full-length front porch on the east and north sides.

It was added to the National Register of Historic Places in 2009.[9]

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Shelter Island Heights Historic District

Shelter Island Heights Historic District
wikipedia / Americasroof / CC BY-SA 3.0

Shelter Island Heights Historic District is a national historic district located at Shelter Island Heights in Suffolk County, New York. There are 141 contributing buildings and one contributing structure.

It was added to the National Register of Historic Places in 1993.[10]

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