Oklahoma Hall: A grand hotel built in 1876 on the shore of Lagoon Pond in Vineyard Haven that was intended to be the centerpiece of a 664-lot subdivision between the pond and the Edgartown-Vineyard Haven Road (then County Road). The plan, led by Howes Norris and E.T.T. Smith of Vineyard Haven, envisioned a densely packed community along the lines of Oak Bluffs’ Wesleyan Grove. But there was no land rush: the hotel failed to attract visitors due to its “remoteness,” and ultimately only six original lots were sold and built into cottages before the whole scheme was abandoned. After being bought by Dellon Dewey and Tom Karl, a famous tenor in American operetta, the hotel was renamed Innisfail and had a second life. With its new celebrity ownership, guests flocked to the hotel on the bluff overlooking the Lagoon. “This is one of the most attractive spots on the Island,” declared the Vineyard Gazette in June of 1898, and it was, until it burned down in May of 1906 and was not rebuilt. Houses have since colonized much of the original property, including the site of the old hotel, but a steep and lovely parcel was donated by Henry Cronig to Sheriff’s Meadow in 1971 to form Brightwood Park sanctuary.

On Time: The third motorized ferry to Chappaquiddick and the first of three ferries of that name. Forty feet long, fourteen feet across the beam, and originally captained by Foster B. Silva, the On Time traversed the 527 feet between Edgartown and Chappy for twenty-seven years. Local legend has it that her name, and those of her successors, On Time II and On Time III, was a play on the fact that the Chappy ferry has no set schedule. Actually, it’s because the original eleven-ton vessel was built in just eleven days and made the tight launching deadline of Sunday, August 2, 1948.

Osborn, Samuel Jr.: 1823–1895. Edgartown storekeeper, whaling mogul, debt dodger, sheriff of County of Dukes County, and manipulator of public records. One of seven children, around the age of twenty he opened a store on Main Street in Edgartown, but a few years later was charged with failing to pay $10,000 in bills.   

Unable to make bail, he was held in the county jail for more than two months. Fifteen years later he got the chance to set the record straight when Governor John A. Andrew appointed him to serve out the term of a Dukes County sheriff who had died. He retrieved the old files from his case, which had ultimately been dismissed, and wrote a lengthy rebuttal in the margins.

By that time Osborn had made a fortune in the whaling industry. By 1880 he was considered the largest individual owner of whaling assets in the United States, with a fleet of eight vessels that annually brought in about $600,000 – over $13 million by today’s standard. When he died at the age of seventy-two, the Vineyard Gazette noted that “In his passing away Edgartown loses a citizen who contributed much to the upbuilding and maintaining the name and fame of his native town.”