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The History of the Charlotte Inn

Yes, There Was a Charlotte…
The imposing three-story home on South Summer Street was one of the most handsome in the village of Edgartown – built to shelter, impress, and capture the grandness of its age. Yet it went through three distinct lives – and almost to ruin – before it was transformed into today’s Charlotte Inn.


The house was constructed by Samuel Osborne Jr., one of the last successful whaling ship owners of the 1800’s. Osborn, a local man whose family built the Osborn Wharf, now the site of the Edgartown Yacht Club, joined the whaling business at a time when most of that industry had already gone to New Bedford. Osborn built the house for his wife, Zoraida, and his two sons, carting many hundreds of loads of earth to the site to raise the level of the boggy land, which had been a low spot and a favorite ice skating place for Edgartown children. By the time the house was finished in January 1866, it was a sparkling center of entertainment, befitting his status as a political and business leader.


"Edgartown's Charlotte Inn ~ A classic example of the traditional New England Country Inn, combining elegance with a quiet, comfortable atmosphere." ~ The Boston Herald


He was one of the most prominent young men of the island. During the Civil War years, he was a member of Governor John A. Andrews’ council. Osborn’s ship the Ocmulgee was the first vessel burned and sunk by the Confederate privateer Alabama in 1862 during raids that eventually destroyed sixty-nine vessels and inflicted a devastating blow on the sea-carrying trade of the North.


The house remained in the family until the early 1900’s, when it was purchased by another man of the sea, who erected a red Victorian porch and a large sign declaring a new use. Manuel Silva Jr. was the oldest son of a Portuguese immigrant, a sea captain who shipped out as a cabin boy at age thirteen. After retiring from the sea, he ran a grocery store on South Summer Street for twenty-five years, moving it several times before winding up in the old Osborn place. His store was considered the most up-to-date and valuable trading place in town. There were kerosene cans in the back, shelves of canned goods in front, and an arresting Victorian porch to advertise it all.
In 1922, he sold the business to Charlotte and Philip Pent, a couple from Staten Island with deep Vineyard roots. Pent was the son of Samuel Pent, the first volunteer from Edgartown when the Civil War broke out. Eighty-three years earlier, Pent’s grandfather had himself founded the grocery eventually bought by Manuel Silva. Now the Pents retrieved ownership of the store and their Vineyard lives. A few years later, the changing economy began to impact the Summer Street Grocery. Chain stores came to the Vineyard, the depression hit, and the Pents saw their business dwindle.


The year 1934 was not an easy one for changing course, especially to start a business as risky as an inn catering to tourists on an island seven miles off the coast of Massachusetts. Yet Charlotte Pent met the skepticism with “a familiar twinkle in her eye”, according to the Vineyard Gazette. Carpenters pulled off the ornate red veranda and built the present entrance. The first-floor store, with the shelving and stacked groceries, was revamped into a spacious parlor and a large dining room, along with eleven guest rooms and five baths. “Everywhere great care has been taken to preserve the simple dignity and beauty which goes naturally with the old house”, the Gazette said.
Charlotte Pent named the Inn for herself, and the transformation was a success.
In 1955 Charlotte Pent, by then a widow, sold the property after which it changed hands twice over, while the buildings and grounds grew increasingly unkept. That all changed in 1972 when Gery Conover, having just moved to the island, took a spring stroll and stumbled upon the building and curiously wondered if it was for sale.
Since then, Gery and his wife Paula have been the proud owners and innkeepers of The Charlotte Inn.