First Settlers

While the early settlers on the North Fork arrived from England seeking a haven for practicing their religion, the first Europeans to settle on Shelter Island were wealthy sugar merchants from Barbados seeking the stands of white oak to use for their barrels. A partnership of four purchased the island from the Manhanset Indians, whose sachem, or chief, was Yoki (Pogaticut), but only one of them settled here. Nathaniel Sylvester brought his 16 year old bride Grissel to Shelter Island in 1652. (Grissel was the daughter of Thomas Brinley, keeper of the accounts for both Charles I and Charles II.)
 

Before they arrived, a substantial house had already been built on a spot not far from the present Manor House on Gardiner�s Creek. With them on the ship were all the furniture and goods required for the house, including family heirlooms, but in a violent storm, not far from port, the ship was dashed against rocks and although most of the passengers survived, few of the possessions were saved. It must not have seemed a fortuitous beginning.
 

But, it was not long before the house was furnished and ready for visitors, of which there were many, including prominent Quakers who were being prosecuted throughout the colonies. They found asylum on Shelter Island. The Sylvesters, royalist refugees from Cromwell�s England, understood the Quakers� plight. The Sylvesters� social life was centered in Newport where other political refugees loyal to the monarchy had found safety. The monarchy was restored in England, and in 1666, Shelter Island became a Manor. By 1673 Nathaniel owned the entire island.

The First Land Division

When he died in 1680, Nathaniel�s estate was divided among his five sons, two of whom eventually gained control, Giles with four-fifths and his brother Nathaniel II with the remainder. In 1695, Giles sold one-quarter of the island, now known as Mashomack Preserve, to William Nicoll of Islip. (The Nicoll family cemetery is near where the old farnistead was located and is still used by Nicoll descendents.) In March 1700, Nathaniel II sold 1,000 acres in the center of the island to George Havens. By 1730 there were 20 families on the island and the town was incorporated. William Nicoll II served as the first supervisor.

Nathaniel II�s son Brinley inherited the Manor in 1728. He replaced the old house with the present Manor House in 1733.

Residents of the island attended religious services in Southold. Brinley attempted to build a meeting house on Shelter Island in 1732, but it was not until 1743 that Jonathan Havens, Jr. gave a half-acre of land in the middle of the island and a meeting house was erected on the site of the present Presbyterian Church. Brinley provided the preacher, William Adams, who was on the island as tutor to the Sylvester children.

Mary (ne Sylvester) inherited the Manor from her father. She was married to Thomas Dering, a well-known merchant from Boston. Dering assumed the role of gentleman farmer, and with the assistance of his servants and slaves, cultivated the broad acres of his wife�s estate extensively. This family was educated and cultured. They expanded the gardens and entertained extensively.

More Growth

During these years, the island�s population increased with the selling and inheriting of land. New names appear in the records: Case, Conkling, Prince, Bowditch, Tuthill, Brown, Duvall, King, L�Hommedieu, Payne, Parker, Sawyer. There were no real roads, but ox-cart tracts ran from the north ferry rowboat service run by the Southold Budd family at Jennings (Stearn�s) point and the south ferry connection at its present location. The Tuthills on Ram Island would drag their scow to Dinah�s Rock at Hay Beach and row across to Oysterponds, now Orient.
 

The Revolution

At the time of the American Revolution, Sag Harbor was an important port, equal to that in New York. It was strategic to the British who captured Long Island early in the war.

In 1776, Thomas Dering was a delegate to the Third Provisional Congress in May through June in New York and again in White Plains in July when the Congress unanimously adopted the Declaration of Independence. He was elected a member of the Convention which met in Fishkill in August to form a constitution for the State of New York. He removed his family to Connecticut for the duration of the Revolutionary War.

Upon returning Dering found that the island residents had suffered at the hands of the British and that his woods had been decimated. Hay Beach is so called because the hay and other goods the British expropriated from the residents were loaded on their ships at this point. Dering was instrumental in helping those who had lost their land during the upheaval to regain it. He died in 1785.

In 1786, Jonathan Nicoll Havens was elected to the New York State Assembly where he serve for nine years. He served in the United States Congress from 1795 to 1799 when he died at age 42.

By 1790 a few more families had arrived on the island: Boisseau, Clark, Gardiner, Griffing, Harley, Jessup, King, and Moore. There was a school house. There were 177 free men and women and 24 slaves. William Bowditch was supervisor, a post he held from 1794 to 1820.

The first custom grist mill was installed on the island in 1810 although Nathaniel Sylvester had a small horse mill for his own estate�s purposes. Daniel Lord was building ships on West Neck Creek. In 1817, the first Presbyterian Church, built on the site of the meetinghouse, was dedicated.

Sylvester Dering, who had inherited his parent�s estate, was at one time a General in the militia, and the manor was called the General Dering Farm. He fell from his horse in late September of 1820 and died 14 days later at the age of 61. Also in that year, Squire Frederick Chase became supervisor. Chase owned the land at what was then called The Prospect, now The Heights. He envisioned that someday his land would become the site of a great city. He laid out the streets and named them. He even sold some lots.

In 1828, the first road connecting the two ferries was completed. When the north ferry landing was changed to its next location in Dering Harbor in 1852, a new road was built and the old one along the shore was abandoned. Resurrected in the early 1890s, it became the public access to Crescent Beach.

1820s - 1860s

In 1823 Samual S. Gardiner married Mary Catherine L�Hommedieu, a granddaughter of Nicoll Havens of Shelter Island and a lineal descendent of Nathaniel Sylvester through her father Ezra L�Hommedieu, a great-grandson and a prominent citizen of Southold. Following Dering�s death, the property became that of Ezra and Mary Catherine inherited it from him. Gardiner, an able lawyer, became squire of the manor which was then called Lawyer Gardiner Farm. Apparently, people came from miles around to hear him argue in court in Riverhead.

Throughout these years, whaling was an important industry in this part of the country and Sag Habor was a principal port with nine ships in 1829. Whaling ships also went out of Greenport, four in 1838. Many of the island�s young men participated in whaling with 30 captains from the island at one time or another. In June 1850, a whale was caught in the ferry between Shelter Island and Greenport, resulting in 10 unexpected barrels of oil.

In 1845, there were 446 people on the island. Most were farmers making respectable livings. Daniel Lord, pastor of the Mariner� Church in Boston and son of Island ship builders, returned home to his estate at Menantic because of bad health. In 1848, he was installed as the pastor of the Presbyterian Church.

In 1849, more than twenty men from Shelter Island joined the rush to California to find gold. Some were successful in enterprises in California, but none found gold.

Twenty-five young men from Shelter Island served in President Lincoln�s army during the Civil War. Five died; others were wounded.

Menhaden

As whaling waned, menhaden or �moss bunker� fishing began in earnest. These fish provided two products: oil and fertilizer. The schools of fish were caught in large nets and thrown into the hold of the boat. When brought to land, they were processed in a fire and kettle known as Pot Works. The first of these was on Chequit Point, but the smell of it wafted across the island annoying the inhabitants. So, it was moved below the bluffs at White Hill where the Scudder family compound is now located. It remained there until the Chase property was bought in 1871 by the Shelter Island Grove and Camp Meeting Association.

 There was another Pot Works at Dinah�s Rock until 1864. Menhaden fishing remained a big business and bunker boats continued to ply out of Greenport into the 1950s. Phosphate factories existed on the island at Dinah�s Rock, Ram Head near the mouth of Coecles Harbor, and at Burns Avenue. At one time there were two factories on Ram Island Beach, and the area was know as �Bunker City.�

A Turning Point

1871 marked a turning point in the character of Shelter Island. The same families farmed the land, but a new population came to the Island: the summer folk. Rapidly, The Prospect became a full-fledged summer resort with hotel, restaurant (now the Chequit Inn), chapel, bathing pavilion, tennis courts, and houses. It looked within a few years the way it looks today except for the hotel which burned down in 1942 and the large bathing pavilion which was destroyed in the hurricane of 1953.

The following year, in 1872, a partnership of Boston men purchased the area then known as Locust Point (now the Village of Dering Harbor) from the Horsford family, the squires of Sylvester Manor. Manhanset House, known throughout the Eastern seaboard as an elegant resort, opened in 1873. The cottages built around this resort took on an entirely different flavor from those across Dering Harbor. The guests were wealthy yachtsmen who could safely moor their magnificent yachts in the secluded harbor. The New York Yacht Club had a station in the harbor, and the Shelter Island Yacht Club was founded in 1886. The first hotel burned in 1896 and was replaced by another, but this one burned down in 1910, never to be rebuilt.

Summer residents came on ships that sailed between New York and the resorts and by train to Greenport. They were heavily ladden with baggage, as they brought all they would need for summer comfort, from bed linens to table linens, from table flatware to cooking utensils. And, of course, the servants.

Ferry service was improved dramatically in 1893, with ferries similar to those used around Manhattan, but smaller.

At about the same time three businessmen bought up large holdings, Francis M. Smith--borax king from California, Artemas Ward, in advertising, manufacturing, and publishing in New York. and the Roe family, from Brooklyn, settling at Westmoreland Farm. The Roe and Ward houses still stand and a number of summer homes circle Smith�s Cove.

After World War I

Real estate activity slowed during World War I, but between 1920 and 1930, there were significant purchases. Two camps were established in 1922, Camp Quinipet and Dr. Pettit's Camps. Montclair Colony was developed by Albert and Fred Dickerson on West Neck Harbor. The residents formed the Menantic Yacht Club. Other developments started on Ram Island and on Silver Beach.

The property on Sachems Neck was sold by the Nicoll Family, which had farmed it for 230 years, to Otto Kahn, a New York businessman. It then passed to the Gerard Family. A consortium was prepared to purchase and develop the land in the 1970s when the Gerards sold the land, 2,000 acres, to the Nature Conservancy to be held in its natural state in perpetuity. Half of the money raised for the purchase came from donations from residents of Shelter Island.

During the Depression, Shelter ls!and suffered like the rest of the country. People could not support their second homes. Many were abandoned. The cottage that author Faith Baldwin used in Hilo Farms was left to rot.

The list of men and women who served in World War II is a long and honored one. It can be seen on a tablet in front of the Legion Hall in The Center.

After World War II

Shelter Island was slow to recover from the Depression and the War. Few families could afford second homes. Children who lived or summered on Shelter Island during this time spent days (and nights) exploring the old abandoned houses.

 During the 1950s farmers on the island created a cooperative to farm and process lima beans. They were sold to Libby�s. But, finally farming died out on Shelter Island, and now there are few crops grown except for family private use.

But, a new generation of summer people appeared. The first resurrected the old summer houses and cottages that could be saved. And then they started constructing new houses. In the 50s and early 60s the growth was slow.

Shelter Island has suffered from many hurricanes over the years, but the one in 1938 will not be forgotten. The damage to houses and trees on the island was considerable. Carol in 1953 was also devasting. And Gloria, in 1985, though not up to expectations, destroyed many trees and left islanders without electricity for up to 10 days. Bob in 1991 Left many homes without power for 10 days and destroyed many sailing vessels in Dering Harbor.

Shelter Island Today

Just over 100 years ago, Shelter Island was a farming community with a few fish factories lining its shores. Today it is a summer resort. There are about 2,500 permanent residents, and the population swells to over 8,000 in the summer. Land is very dear. There are at least 40 current building permits out at any one time.

There are two post offices, one in The Heights and one in The Center. The library and a school for grades K through 12 are in The Center. There is a unified volunteer fire department. Golf can be played at both a public course and a private club. There are four public beaches and a beach club. The Yacht Club remains a social and yachting center for many summer families. Hotels of every size
and style and a variety of restaurants meet every taste and purse. Daily newspapers are available at the Pharmacy in The Heights and at Tom�s in the Center. Stores provide everything a visitor should need. There is no movie theater and never will be.

The widow of a descendant of Nathaniel Sylvester resides in Sylvester Manor on Gardiner�s Inlet, not visible from any road and not open to visitors except on special occasions of the Garden Club, the Shelter Island Historical Society, or the Education Foundation. Descendents of many of the families on Shelter Island during the American Revolution are still here. And, a number of families can claim summering here continuously for five generations.

Casual visitors to Shelter Island are warned that the ferry line, especially for The North Ferry, can be very long on summer weekends.  If you are just visiting for the day on a weekend, don�t bring your car over; walk or bike onto the ferry.

Post Offices:
The Center 11964
The Heights 11965

Ambulance, Fire, Police : 911
State your name, address, phone number, cross street, and the nature of the emergency clearly.