The village of Holmes Hole, as Vineyard Haven was called until 1871, had only two streets - Main Street and Beach Street, both located where they are today. Beach Street continued above the comer of Main and was the road up-island, as it is today.

The entire Main Street from the site of the present Martha's Vineyard National Bank to the site of the Youth Center, was reduced to ashes by the Great Fire of 1883. You will find no old houses on that part of Main Street.

William Street was laid out in 1830. Most of the houses on that street were built between 1830 and 1860 by the master mariners of the Whaling Period. The first built was that of Capt. Richard Luce, 1833, now owned by Mrs. McAdoo.

1. '1785 House', apartments. Owned by Mrs. Frank G. Johnston. Built in 1785 by Samuel Daggett, whose son was a fifer in the Revolutionary War. Edward Hanson Smith (1889-1961) was born and grew up in this house. He made his career in the Coast Guard, rising to the rank of Rear Admiral, and earned the nickname 'Iceberg Smith' because of his work with the ice patrol in the North Atlantic.

2. Owned by Capt. Robert S. Douglas. Built in 1801 by Capt. Seth Daggett, in whose family it remained for four generations. Capt. Daggett was a pilot, so this situation was ideal for him. The harbor came much nearer to the house than it does now. The story is told of him that he particularly disliked serving British vessels, so one night when he heard them coming after he had gone to bed, he took off for the woods, seizing some clothes as he went. The next morning he discovered the clothing he had taken was his wife's.

3. The old Claghorn Tavern, owned now by Thomas deMont, was built by Samuel Claghorn. His son Joseph kept the tavern there. The sign, dated 1792, hangs in the Nathan Mayhew Museum. A later tenant was postmaster Parsons, who kept the post office in the ell, and delivered letters through the window. Mr. deMont has made the old tavern into apartments, preserving much of the old paneling and other features.

4. Owned by John N. Chase, since 1957. Built about 1828. It is framed in hand hewn hard pine, and has unusually thick interior doors. The staircase is of the curving, self-supporting variety, typical of that period.

5. Facing Beach Street - which once was more often called Quality Street - is the home of Mr. & Mrs. Henry A. Ritter. It was built in 1796 by Rufus Spalding, a leading citizen of the town at that time. Early in the 1800's, it became the property of Stephen deNeuville, a young French sea-captain, who one day sailed into Vineyard Haven harbor, fell in love with a Vineyard girl, and settled down here. His family and descendants lived there until 1902, when it was bought by Capt. Gilbert Smith, who sold it to the Ritters.

6. The Co-operative Bank was built as a dwelling house in the early by Capt. Matthew Luce. Eventually it came into the possession of Mrs. Grafton Daggett, who was living there the day of the Fire in August 1883. As the Fire rushed nearer, Mrs. Daggett spread quilts and heavy blankets on the roof, and wet them thoroughly, bringing water in buckets up through the sky light. Desperately, she called for help. A completely unknown young man appeared, who said he came from a vessel in the harbor, and he promptly began carrying the heavy buckets to the roof. When the Fire was finally over, the young man disappeared, leaving his hat which he had laid aside. He never came back for the hat!

7. Owned by Mr. and Mrs. William Mangin. This is one of the five oldest houses in the village. It was built in three stages. The first part was built in the 1700's, as its lines clearly show, and moved to its present site, probably be fore by Capt. Lot Luce. Either he or his son added the second part of the house. The kitchen and garage were added about fifty years ago. It has had several owners and has always been occupied.

8. 'The Old Dexter House' has been so known since it was built in 1730. The present owner, Mrs. Wm. B. Leatherbee, is a descendant through her mother, of the Dexter family. The house is typical of second period colonial. No alterations have been made on the outside to affect its austere beauty.

9. Owned by Mr. and Mrs. Manuel Viera. Originally owned by Capt. Joseph Dexter, the main structural lines of the house would place it back in the 1700's. The dormer windows suggest a modern, though not unbecoming touch.

10. Owned by Mr. and Mrs. David Whittemore. Built by Elisha West, probably in 1743, when his brother Peter built a house next to it, now demolished. Peter West was killed in the French and Indian War, but Elisha seems to have lived out his natural life. This house has one brick wall, about which many stories have grown up, quite likely wholly imaginative.

11. Owned by Mrs. Ralph deGolier. Built in 1745, and except for the addition of a piazza across the east front, has not been changed. It was built by Timothy Merry and was owned by three generations of his descendants. During the Fire in 1883, fire fighters drew water from the well here.

12. Capawock Hall - now the Masonic Hall - escaped the Fire. It was built in 1833 by the Methodists for their church. In 1845 the Methodists built a new church, larger, and very beautiful, in the colonial tradition. It stood across the street where the present Methodist Church stands. It was destroyed by fire December 31, 1922, and the present one was built of stone 'so it couldn't bum down'.

Meantime, Capawock Hall was used for concerts, lectures, balls and other secular affairs. In 1895 it was bought by the Masonic Lodge.

13. Owned by Mr. Rudolph Stam, apartments. Date not known, but its original lines say '1700's'. Home of Capt. Wm. Harding. He had six sons, all of whom grew up to be whaling captains. The old house spent twenty years or so on the beach in the early 1900's, as a men's club, the Nobnocket Club. After this experience it was returned to its original location and function.

14. Occupied by Mr. Robert Hyde; owned by Mrs. Lisette Knight. Homestead of Jonathan Manter, built in 1712. This is one of the five oldest houses in the village, according to the historian, Mrs. Norris. Jonathan Manter died in 1820, leaving the house to his spinster daughter, Rebecca. She married Deacon William Downs. They kept a grocery store there.

15. Owned and occupied by Mrs. Lisette Knight and family. This house-lot, which like most others at that time, reached from the harbor to Tashmoo Pond, was Jonathan Manter's wedding gift to his youngest daughter. She was named Parnell, for her oldest sister who was one of the Liberty Pole girls, and who died in 1777. The second Parnell married Alexander Newcomb in 1801. They built their house on the lower end of the property facing the harbor.

16. Owned and occupied by Mrs. Lisette Knight and family. The Newcombs built this house soon after their marriage for Mr. Newcomb's mother. After her death the house changed hands several times.

17. Owner, Mrs. Frank Vincent. The house is obviously a very old one, excellently kept up. The early part dates from the return of a Revolutionary soldier, Malachi Baxter, after fighting at Bunker Hill. The present owner's husband was a descendant of Baxter through his daughter and granddaughter. Except for the addition of the piazza, there have been no structural changes in the house since it was built here.

18. The Nathan Mayhew School House was built in 1828 for a 'north end' school. It was built by Nathan Mayhew, who also taught the school there for several years. On Sundays the building became the Congregational Church, and the name 'Mayhew Chapel' has stuck to it. Eventually both school and church found other quarters and the little building was given over to business, until its purchase in 1903 by the Sea Coast Defense Chapter, D. A. R. It holds an excellent small historical collection.

19. Owned and occupied by Mrs. Emory Morse. Built in 1805, by Edmund Crowell when he married Deliverance Chase. Four generations of their descendants lived here before it was sold 'out of the family'. In the parlor of this house was a remarkable over-mantel painting on the wood panel. It was done by an Island woman when the house was built, and the woodwork in the room was delicately carved in the style of the times. It was the inspiration of a recent owner, Mrs. Gustav Murman, to present the whole room to the Smithsonian Institution, thus preserving a priceless period piece for following generations.

20. Owned by Mr. and Mrs. Peter Jay. Built by Capt. Thomas Harlock Smith in the early 1800's. It remained in his family for four generations. He was first mate of the whaleship Sharon at the time of the mutiny in which the captain was killed (one of the famous horror stories of whaling) and completed the voyage as captain.

21. Owned by Mrs. Charles M. Earle. This house was built down the neck, and was moved to the village on wheels, drawn by forty yoke of oxen. Barzilla Luce had the contract and farmers from all over the island came to assist. Porches were added, probably in the mid-nineteenth century, but there is little change inside.

22. Owned by the Clough family. Built about 1810 by Captain Charles West. Originally of the familiar colonial type, it was practically made over by a later owner, Mr. Wendell Crocker, about 1870. He greatly enlarged it, raised it a full story, added bracketed eaves, 'mill work', a balcony and a veranda. The present owners are Mr. Crocker's daughter's descendants.

23. Owned and occupied by Mrs. Janet Swift. This is a very old house, probably prior to 1800. It was built in Lamberts Cove and brought to Vineyard Haven in 1809, by water, dragged up from the beach by oxen. Modernized enough for today's living, the old plan nor architecture has been materially changed, although an additional bedroom has been built in recent years on the water side.

24. Beachside, owned by Captain Robert S. Douglas. Built in 1802, by Squire Thomas Dunham. Squire Dunham was master of a merchantman in the foreign trade. He was prominent in town affairs and held several town offices. He was also a pilot, and kept here a tavern for sailors, known as the Rising Sun. The south-cast room was a store, chiefly for the sailors, kept by his daughter Sally. After the deaths of Squire Dunham's son and his widow, Beachside was sold at auction and was bought by Mrs. Joseph Chase who was the squire's granddaughter. It was the home of two more generations of Chases before Captain Douglas acquired it.

25. Beachside land originally extended to Main Street. The upper part is now - since 1955 - owned by Mrs. Marianna Winslow. As the Captain's House it is widely known for gracious hospitality. This house was built, about 1915, Isaac Chase, who converted it from the Beachside barn which he moved from its original site directly cast of Mrs. Swift's property. It was seriously damaged by fire in the 1930's, but restored. Many of the original timbers are still there in attics and cellars.

26. Owned by Mrs. Morison Sharp. Built in Lamberts Cove in 1720, on the familiar slant- roof, single chimney plan in use then. It was moved to Holmes Hole by sea in 1820, dragged up from the beach by many yokes of oxen. At one time, a school was held there. Once two families occupied it, both using the same fireplace for cooking. Late in the nineteenth century it was owned by a Mrs. Richardson, who had it moved back from the street, a full upper story added, the big central chimney taken out and the piazza added. A succession of owners since then have not made radical changes in the house.

27. Owned by Mrs. Bayes Norton, Sr. Built 'doubtless before 1750' says the historian, Mrs. Norris, by Abraham Chase, Jr. It was inherited by his son Timothy who was a Lieutenant of Militia in the Revolution. His son exchanged this property for a farm in West Tisbury, and that owner's son sold it to Mr. Rodolphus Crocker from whom the Norton family inherited it. It is likely that many of the architectural changes in the exterior of the house, originally of the familiar early colonial type, were made by Mr. Crocker. The story has been handed down with the house, that the cow was hidden in the house during Grey's Raid in 1778.

28. The old Windmill has been a landmark since the early 19th century, perhaps even earlier. It stood originally near Spring Street, on what is now Mrs. McAdoo's property. It has been moved twice, first to a site on Mr. Donald Tilton's home property on Main Street, and from there to the present property of Mr. William H. Snow.

29. Owned by Mr. and Mrs. William H. Snow. Put together, rather than built, by General A. B. Carey, in the 1880's. General Carey added the Windmill to a house already made out of two very old houses. The older of the two was the home of 'Aunt' Molly Merry, who kept a sailor's tavern there in Revolutionary times. Aunt Molly was a 'character', of whom many tales have been told, and a miser, who kept her money in hard cash tied up in pudding bags and secreted under the stairs.

To the original house there was added a part of a house moved from Chappaquonsett. It was the home of Mrs. Rhoda Luce, who lived to be over one hundred years old.

30. Owned by Mr. and Mrs. Robert Scott; apartments. Moved to present site from Owen Park, where it was built in the early 1800's by John Hursell. Through the years it has been so remodelled and rebuilt that no vestige of the old house is left. In the mid-19th century, it became the home of Mrs. Christaline Johnson, who kept there one of the earliest boarding houses for summer visitors.

31. Owned by Mrs. John Andresen. This house too was moved from Owen Park, where it stood on the shore next to Mrs. Earle's present home. It was built between 1801 and 1805 by Benjamin Allen. He was a rank Tory, and not at all popular in the village. Rev. William C. Hicks, rector of the Episcopal church in the village from 1894-1898, was the last owner before Mr. Owen purchased it and moved it to its present location.

32. The Great House. Owned by Mrs. Marian Warner Trotter. Built by Abraham Chase about 1720 on a site close to and overlooking the harbor, now the Town parking lot (next to the A & P). It was quite the grandest house, and its owner was quite the most important man in the village. It was moved to West Chop in 1922.

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