Houses Built Before 1870 
1870 is a pivotal year in the history of Shelter Island. Until then, the inhabitants were farmers and mariners, including many famous sea captains. There were approximately 90 families and less than 600 inhabitants. 
When these houses were built, there was no telephone, electricity or indoor plumbing. They were not insulated. Evans Griffing tells of building a barrier around the house and filling it with seaweed collected on the beach for insulation around the foundation in winter. Transportation was by foot, horse, or horse and wagon. Most of the land was farmed and there were few trees. Coal was imported by ship and carted by wagon to the houses. Throughout the Island, there were families who ran small general stores out of their homes. There was a "public highway" from the Clark's ferrying operation to North Haven north to where the public dock on Bridge Street now stands. It was dust in summer and mud in winter. There, in 1853, Jonathan Preston began ferry service to Greenport. Previously, there had been erratic ferry service from Jennings Point to Southold.

The railroad had come to Greenport in 1844, and farmers and fishermen were beginning to sell their crops, from the land and sea, to customers in New York City

Only two families summered here: some members of the Havens family, and Professor Eben Horsford, a Harvard professor who owned the ancestral home of the Sylvesters.

In 1871, the Shelter Island Heights Methodist Camp Meeting Association purchased Squire Chase's acreage on The Prospect. The hotel was built and the entire area to West Neck Road was laid out for thousands of summer cottages. Although that extensive project failed, Shelter Island instantly became a summer family wonderland. Dering Harbor was quickly active as a yachting haven with two huge and very popular summer hotels on either side of it. The Manhansett House burned for the second and last time in 1910, and the New Prospect burned in 1942 never to be rebuilt. However, the Island had changed forever.

So we honor those first families, with this old house trail.

These are their homes. The names are old family names of many who still live on the Island. Havens, Bowditch, Griffing, Conkling, Dickerson, Sherman, Wilcox, Duvall, Cartwright, Burns, Tuthill, Jennings, Case, Clark, Congdon, Ryder, Payne, Manwaring, Walther, Nicoll, and Lord.

All properties are private; we request that you not trespass, but view only from the street.

1. 132 South Ferry Road. Built by a member of the Havens family about 1776 (an English penny of that year being discovered in the foundations when the building was renovated), this house was acquired in 1858 by Samuel G. Clark and is now owned by his grandson Donald H. Clark. First built with a central chimney, the house has been expanded or renovated three times since 1903 and now has chimneys at either end. Among the remaining original features of the structure are the upper windows and those lower windows that face the road. The Clarks supplemented the income from their farm by rowing travelers across to the mainland, sometimes in competition with the Tyndal brothers of Hog Neck. 
2. 125 South Ferry Road. When David and Samuel G. Clark, Jr. (sons of the above Samuel G. Clark) married Adelaide and Elizabeth, daughters of Stratton Havens, about 1865, they built this double house. The original house plan was not quite a mirror reverse plan, for an open center hall both down and up was shared by the two sibling couples and their only children. Most of the original six-over-six windows are still in place with their old glass panes. These windows are unusually low- being only 18" from the floor. An 1894 photo of the North, or Sam Jr. side, of this house, shows a large addition that was used as a summer boarding house and a front porch with 6 pillars and much gingerbread. The full cellar has its original fieldstone foundation held together with 
 oyster shell grout. 
3. 70 South Ferry Road. One of four houses in this inventory built between 1820 and 1849 by Gabriel Crook, this home occupies a site across from where the builder's own residence stood and was first owned by Capt. Sylvester Cartwright, a whaler. In 1849 Crook left the island to join the California gold rush and, according to Lodowick Haven's records, eventually "got Home."

4. 40 South Ferry Road. Originally a barn, this house was converted sometime before 1740 and occupied by Elisha Havens Pain (sic) during his term as town Constable and Collector, 1740-1748. In 1781 British soldiers were dissuaded from burning the building by Pain's widow Deliverance who bribed them with a silver tankard, some linen, a watch and a "fowling piece." Threatened again by marauding British soldiers in 1812, the house was again spared. During recent renovations, portions of the walls were found to be filled with bricks and a penny dated 1802, and a scythe was found lying across the rafters. 
5. 16 South Ferry Road. "Heartsease", now known as "Havens House," was built in 1743, and served as both residence and store until the 19th century. It was the home of Capt. James Havens, member of the Provincial Convention of New York (1775- 1776). During the British raid in I 781, soldiers carried off the captain's watch, a coat and several "fowling pieces." Site of the annual town meeting between 1783 and 1785, the house is now home of the Shelter Island Historical Society. 
6. 9 North Ferry Road. A retired whale ship cooper, Archibald Havens, built this house in 1840 and then raised a store just west of it. In addition to selling groceries, meats and hardware, Havens served as postmaster for fifty years and as town librarian. 
7. 38 North Ferry Road. "The White House," originally a salt box, was built before1850 and acquired a second story about 1875. The long shed-like barn located behind this house was where the village blacksmith, Joseph Congdon, plied his trade. Joseph himself lived in the Dew Drop Inn. 
8. 80 North Ferry Road. "The Farm House" at Sylvester Manor consists of what were originally two separate structures. The main building, built about 1840, was joined some thirty years later to an older structure (built before 1800 and used as a barn) brought from another part of the Manor. (This house cannot be seen from the road.) 
9. 80 North Ferry Road. Sylvester Manor stands on the site of the Island's first house, which was built in 1652 by Nathaniel Sylvester. The present Georgian residence dates from 1733. The water garden near the home was designed at the end of the 19th Century by the famous botanist Asa Grey as a house present. On the lawn lies a French cannon, one of two believed to have been buried during the Revolution when a British fleet sailed into Gardiners Bay. (This house cannot be seen from the road and can only be viewed by private invitation or from Gardiners Creek.) 
10. 100 North Ferry Road. "Creek Cottage," built about 1740 for the Rev. Mr. William Adams, chaplain to Brinley Sylvester, has been periodically enlarged and renovated over the years. Sometime between 18 I 6 and 1857, Richard F. Nicoll is said to have established a private school here. (May be viewed from the Quaker Cemetery.)

11. 105 North Ferry Road. The Maltby Payne House is another of the Greek Revival style homes built by Gabriel Crook before 1849. 
12. 115 North Ferry Road. Standing since 1826, this house was initially a farm building belonging to the Conkling homestead across the present road. 
13. 118 North Ferry Road. The Conkling-Griffing-Duvall Homestead was built in 1828 by Moses D. Griffing, who married the daughter of Shadrach Conkling, owner of an earlier home closer to the creek. The kitchen of the original Conkling house, a wooden pegged structure, proved too sturdy to raze and was joined to the newer building. Shadrach himself is said to have been fairly sturdy, and local legend recounts his encounter with British soldiers during the Revolution. Asked why his steers could be bought more cheaply than his neighbors' , Shadrach supposedly told the redcoats that the animals' red color diminished their value. In 1858, an el was added to the house that Griffing built, and its present features are said to include a ghost.

14. 166 North Ferry Road. The Bowditch House. Built before 1860. IIn 1870, it was the home of John B. Bowditch who at the time was the commander of a large Pacific mail steamer. His grand-daughter Belle, with her mother Ella and later her sister Edith (By), operated the house as a boarding house until 1972shortly before she died.

15. 168 North Ferry Road. Gabriel Crook built this home for Capt. CCharles H. Harlow. As do all Crook Houses, it dates from before 1849. Soon after 1863, Capt. Harlow was running the ferry to Greenport in partnership with Samuel Clark.

16. 174 North Ferry Road. The oldest house now standing in the North Quarter, this home was built in 1858 by Frank Sisson, and it was occupied by Capt. Jonathan Preston, a ferryman and builder of the first dock on the north end of the Island. Called Middle Landing, Preston's dock was just east of the present town dock. A popular personality of whom it was said "everybody swore by him, nobody at him," Preston continued his ferry service until 1863 in response to local demand although his personal preference would have been to quit and go fishing.

17. 15 West Neck Road. This, the fourth of the Gabriel Crook houses, was built for William R. Duvall, according to his nephew Ralph Duvall. Known as the Wilcox house because in the late 19th century it was lived in by Nathan P. Wilcox who owned the coal, wwood and feed yard adjacent to the town landing on Bridge Street.

18. 27 West Neck Road. The Case-Jennings house was built in 1847 by a member of the Case family and sold in 1882 by Martin L. Prince to Morancy P. Jennings. In the late 19th Century this area of West Neck and south on Menantic Road was known as "The City."

19.31 West Neck Road. c. 1880. Known as the "Ketcham Homestead .. " It stood to the north of what is now the Tuck Shop which was at one time Ketcham's Grocery.

20. 35 West Neck Road. The original part of a house is from the mid1800s. This structure is located in a row of houses of the same period and was probably used as a store.

21. 39 West Neck Road. One of the oldest houses on Shelter Island, a salt box with central chimney and four hearths, this home was also built by a member of the Case family. Although a land deed dated 1725 mentions buildings at this site, no specific mention of this house was made before 1745. Initially, the front of the house faced the road, but the road has since been moved to the other side of the house.

22. 43 West Neck Road. Mid-1800's. Note the chamferred posts on the porch. A part of "The City."

23.,45 West Neck Road. Known as the Brinley-Wiggins house. In about 1870, it was moved to the City from The Heights where it had belonged to Margaret Walters, one of Squire Chase's daughters. Nathan Cuffee, a Native American who wrote "Lords of the Soil," lived in this house in the early I 900s. A part of "The City."

24. 46 West Neck Road. c. 1876. Owned by Eliot Jennings, then Seth Raynor, and then Eldredge Bennett ( 1864-1954) who had a fishing shack on Ram Island where he went fyking . A part of "The City."

25.,47 West Neck Road. c. 1807. It is said that when the six Case brothers came to the Island, each built himself a house. This is one of them. Seth Raynor owned it in 1873. Red clapboard with three bays. A part of "The City."

26.,51 West Neck Road. c. 1859. Was once the home of ornithologist Willis Worthington, a naturalist and Taxidermist. He was an avid collector of birds, bird eggs, snakes, animals, and Indian relics from all parts of the United States. His collection is now at the Stony BBrook Museum. His extensive journals are at the Shelter Island Historcal Society. A part of "The City."

27.,70 West Neck Road. c. 1870. Walthers/Conrad House. It has I II2 stories with three bays, and a gable roof with small windows under the eaves. It has a stone foundation.

28. 73 West Neck Road. An early Payne House built before 1870 when it belonged to Richard Payne. This house is now owned by William Congdon who was greeskeeper at teh Shelter Island Country Club for many years.

29. 81 West Neck Road. Before 1870. The Johnston family house for many years. John Payne is its earliest known occupant, It is said to have been built by Daniel Hudson. The Victorian porch and turned posts were added.

30. 82 West Neck Road. Built prior to 1873 when Benjamin Walthers and his family were known to reside there. This has an original porch and turned posts. 
31. 1 Stearn's Point Road. Built in 1868 by Jonah Dickerson, this house was expanded in 1920 and renovated in 1972 but still has the original beams cut from Shelter Island oaks. 
32. 23 Stearn's Point Road. "The Farmhouse." c. 1853. George Meinhordt, owner of the Shelter Island House, lived here in the early 1900's. This is now known as The Olde Country Inn. 
33.,31 North Menantic Road. The Cobb-Webb house originally stood in Shelter Island Heights. Owned before 1810 by a retired businessman named Cobb and then by his sister, a Mrs. Webb. It was moved to its present location in two sections. The smaller of these, which fell from the transport, remained near the spot where that misfortune had occurred and there acquired new residents. The larger section became the residence of the Walther family. It was extensively renovated in the 20th Century and is now known as Burro Hall. 
34. 84 Smith Street. The Osborn house is a typical vernacular style of Shelter Island. In 1870, it was owned by Captain David C. Osborn. 
35.,67 Smith Street. This Greek Revival house was built for Charles Henry Smith, a clipper ship captain, in 1854. 
36. 27 Smith Street. Sometime before the turn of the century, this house was built for the caretaker of the Flagg homestead. According to an old map dated 1889 a Case family lived here. It has a Greek Revival entrance. 
37.,28 Smith Street. Built in 1858 near South Ferry by Charles T.  Chester, this house was moved in 1900 to its present location and became the home of Albert R. Smith, son of Charles Henry Smith, a potato farmer and Town Supervisor in 1913. Smith Street is names after him. Chester D. Sherman was born in the original house.

38. 5 Sunshine Road. The Flagg homestead was built in 1880 by Henry D. Sherman with stones used in the foundation that were brought as ballast by a ship from Maine. This house has had only three owners, Flagg, Bruges (Brush), and Heineman.

39. 9 Sunshine Road. About 1880, this house was raised by Havens Payne. However, a member of the Congdon family was living there in 1889. 
40. 6 Ward Road. "Greatfields." In 1788, this house was built by Samuel Havens, son of William Havens who built "Heartsease." According to our 1889 map the Treadway family was living here. There was a very comprehensive study of this house dibe in1999 by its then owner Sophia D.L. Truslow which is on file at the Historical Society. 
41. 23 North Midway Road. The Caleb Smith house was built in the late 18th or early 19th century. Caleb married Harriett Bowditch, daughter of Susanne and William Bowditch. 
42. 19 North Midway Road. Capt. Samuel Sherman, a whaler, built this house at the start of the 19th Century. 
43. 59 South Midway Road. c. 1760s. Federal front c. 1850. This was the home of Nathan P. Dickerson, first mate of the famous clipper ship, "The Flying Cloud." which set a record of 89 days and 21 hours from New York to San Francisco via Cape Horn, a distance of. 14,500 miles in 1851. The 235-foot ship was made of New England oak and had as many as 32 sails. 
44. 81 South Midway Road. James Tuthill, born 1803, son of Thomas Tuthill and Abegail Terry, owned the home called "Kemah," an Indian name meaning "in the face of the winds." Probably built in  1750s It was in the Tuthill and Wade families for most of the 19th century and was purchased by the composer J. Donald Robb and his wife Harriet in 1933. They retired as full time Island residents after a quarter century at the University of New Mexico where he was head of the Fine Arts Department. They still played tennis when in their 80s. It is situated on 23 acres, partly meadow and partly hardwood forest, it looks out over 6 miles of water to the south fork of Long Island. The property backs to Fresh Pond. 
45. 119 South Midway Road. Circa 1850. Jame s Tuthill's brother Ezra built this home. It was owned by Tuthills throughout the Nineteenth Century. 
46. 28 Congdon Road. Once the site of Marcus Duvall's store.  Originally, it was built by Capt. Lewis L. Bennett, one of the best spinners of yarns ever to go whaling. Later it was Camp Shelter Island run by the Brooklyn Bureau of Social Service. The large wing on the south side was dedicated the Helen Owen Carey Dining Hall after the wife of then Governor Carey of New York who has a home on Shelter Island. When raised, the building had a flat roof in keeping with its original Greek Revival architecture. Now a private residence. 
47. 29 Congdon Road. All that remains of the Great Central Mansion, the home Jonathan Nicoll Havens, member of Congress 1775- I 799, is incorporated in this house, built by the first Timothy Congdon from the west portion which escaped the fire that destroyed the rest of the mansion. Also known as the Duvall Homestead. 
48.  6 St. Mary's Road. c. 1800, built by a member of the Tuthill family. Charles D. Manwaring, lighthouse keeper on Little Gull Island lived here from around 1858 to 1889. 
49. 36 St. Mary's Road. c. 1873. The house belonged to Griffing in 1873 and in 1889 to Des Anges. Owned by the Shepherd family for most of the 20th century. It is a two story, five bay and gable roof Greek Revival house updated with double decker porch center front with turned posts, sawn balusters on the second floor, turned balusters on the first floor, and sawn decorative fan detail, sunburst motives in peaks of gables, basket weave decoration on peak of front porch, hexagonal bay on the south. The stone foundation can be seen in the rear. 
50. 47 St. Mary's Road. Known as the Lester House. The late Lynn Riggs, author of "Green Grow the Lilacs," lived in this house and  wrote "Toward the Western Sky" here. Originally it was built as a "new" house for Capt. Edward Sands Cartwright, a whaler and brother of Anderson Cartwright, in about 1865. 
51. Bartman Lane. Captain Anderson's "old" house was built between 1846 and 1850. 
52. Manwaring Road. The windmill, now at Sylvester Manor, was built in 1795 in Southold by Nathaniel Dominy IV, a prominent East Hampton craftman .. Bought by Frederick Chase, Maltby Cartwright and Joseph Congdon, it was floated across to the Island to a site adjacent to the site of the present school. It was moved to the present site in 1926 by Miss Cornelia Horsford to preserve it. A typical Dutch mill, it moves counter clockwise and was used for grinding corn and wheat. 
53. 19 Burns Avenue. It is believed that this building was raised by James Jennings. Although not owned by the church, it served as the first Presbyterian manse and was the residence of the Rev. Daniel Hall between 1806 and 1812. Sam Ben Jennings, a Union soldier in the Civil War, made his home here. So rigid was the training in Jennings' regiment that he "marched" forever after, even when herding the cows home. 
54. Willow Lane. Another Cartwright home circa 1872 where Clarence, Clifford, and Ralph were born. Seems to have been much remodeled - porches and fireplaces have been added, partitions removed. In the 1890's the shed back of the house was attached. The shed itself was built in the 1840's. B. K. Crispell purchased 24 acres of Cartwright property on which were located three houses and two barns. This is one. 
55. Willow Lane. This Cartwright home was built in 1816. The kitchen was originally the slave quarters for Sylvester Manor and was located on what is now the eighth fairway of Gardiner's Bay Country Club. It was moved in the 1890's by horse and wagon to its present location. Since the moving job was an arduous one the men doing the work partook too well of the liquid refreshments, it is said, and when they arrived with their burden, dropped it 20 feet short of its goal. 
56. 24 Ram Island Road. The Remington Havens House was probably built in the early 19th century. Remington Havens was a farmer and a miller. 
57. 27 Ram Island Road. George Cartwright built this house soon after his neighbor, Remington Havens. 
58. 41 Ram Island Road. Was probably built around 1866 but its early history is unknown. Was known as Hell House and could be rented for the summer in 1903 for $200. For most of the 20th century it was owned by Lewis and Claire Southwick from whose estate it was sold to John and Elizabeth Holmes. Now Paard Hill Farm, the majority of the property will remain in its present state in perpetuity based on an easement with the Peconic Land Trust. You are welcome to admire the horses from Ram Island Road.

59. 40 Ram Island Road. John Tuthill built this house in 1852 so it could be seen from the original Tuthill family homestead across the inlet on Ram Island (no longer standing). He farmed the hill consisting of 35 acres. It remained in the family until Max Wilkenson purchased it in 1952.

60. 55 Cobbets Lane. Built by Thomas Dering of Sylvester Manor for his son Henry Packer Dering. Started in 1776, when Henry was 13, construction was interrupted by the flight of the Derings to Connecticut during the Revolution. The home was completed between 1781 and 1782. Henry left the Island when he was appointed by George Washington to be the Customs Collector at Sag Harbor in 1790 when that town became the new natKm's first port of entry. He served until his death in 1822. It was purchased in 1872 by Professor Eben N. Horsford of Sylvester Manor who restored it for his daughter Gertrude Fiske and her family as a summer cottage. Andrew Fiske's parents were engaged in this house. It was used as a golf club house by the Manhanset Company from the early 1890s until it was acquired by Frederick and Mary Prime in 1913. They laid out the lovely gardens. A 60 foot stone-lined well east of the dwelling is one of just a few of its kind still existing on Long Island.

The preparation of the original list was primarily done in 1976 and would not have been possible without the cooperation of many knowledgeable Islanders and particularly the help of Mrs. Isabel Bowditch, Mr. Tom Young, Sr. and Mr. William Meringer. Mrs. Sheila Dominy prepared the trail map. The list and map have been updated in 2002 by Patricia Moser Shillingburg. 
Few guides to Shelter Island's past are as illuminating as the Old House Trail, which includes every home known to have been built here before 1870. Absolute accuracy in the absence of complete records is impossible, and so there may well be several homes excluded from this list. The Shelter Island Historical Society is eager to learn of such omissions and to acquire any significant data on the Island's older buildings.

Shelter Island Historical Society