SailorGuides.com:
A Trailer Boat Cruising Guide to Kelleys Island
History
Kelleys Island has a rich and violent history. Although various prehistoric tribes may have populated the island since it first emerged from beneath a great glacier twelve thousand years ago, the earliest identifiable inhabitants were the Erie Indians, who lived there at the time of the first white settlements in the New World. As a result of internal political strife among the Indian tribes, brought about by the appearance of European traders in the region, the inhabitants of Kelleys Island were wiped out by a rival Iroquois tribe, who took possession of the island around 1665. The Erie Indians left behind a fascinating artifact in the form of "Inscription Rock", a large limestone boulder near the present-day downtown, which is covered with a seemingly random assortment of pictographs. Opinions vary as to the meaning of the inscriptions, but it is widely thought that the carvings represent a sort of prehistoric bulletin board upon which messages were left noting which group had carved them, how the hunting had been, and where they were headed to next in their migratory travels.
Shortly after the end of the American Revolution, a geological survey of the area produced the first detailed maps of the region, in which Kelleys Island was officially designated as "Island Number 6". Naturally, this bland name didn't last long and the Island was soon being referred to as Cunningham's Island, after a French pioneer known only as 'Cunningham' who became the first white settler on the island in 1803. Cunningham successfully coexisted with the local Indian population for a time, but the relationship soon soured and he was attacked and mortally wounded by the natives. Several other white frontiersmen attempted to settle the island over the next few years, but all were quickly driven away by the hostile tribe.
The American military arrived in force on the island during the War of 1812 as part of their ongoing operations against the British outposts in Michigan, leading the Indians to eventually abandon it. For several decades after the war, various white settlers established homes on the island, eventually raising the population to a total of six families. By now, small-scale mining of the island's massive limestone deposits had begun and the island's first dock was constructed on the north shore to ship the valuable stone to the mainland.
Among these early settlers was a burley lake captain and reputed pirate named Ben Napier, who claimed ownership of the entire island based on apparently nothing more substantial than the fact that he had once set foot upon it. For that matter, at one time or another throughout his life, he would assert some nebulous theory of squatter's rights to claim ownership of almost every island in western Lake Erie. Napier and a small entourage of unsavory characters took residence in an abandoned cabin in 1833 and informed the other settlers that they were trespassers on his land. He then proceeded to conduct a campaign of terror against them, killing their livestock and generally making their lives miserable.
About this same time, a successful Cleveland merchant named Irad Kelley was forced to land his small cargo boat on the island to escape a storm on the Lake. Irad was a keen businessman and knew prime real estate when he saw it. Along with his brother, Datus, he began purchasing large parcels of land on the island from the locals, who were happy to sell if only to end Napier's harassment. Naturally, this did not go over well with Napier, who filed an endless series of court challenges, each one of which was ruled in favor of the Kelley brothers. Without a legal leg to stand on and the emboldened locals smacking for revenge, Napier finally skulked off the island to pursue a life of petty crime. For generations afterwards, parents on the island would keep their children in line by warning them that Ben Napier would come to get them if they didn't behave.
By 1840, the Kelley brothers had purchased all of Cunningham's Island and immodestly changed its name to Kelleys Island. Over the following decades, the brothers increased limestone production and began harvesting fruit and lumber for shipment to the many new cities and towns popping up across the Great Lakes. About this same time, a member of the Kelley family noticed that grapes grew particularly well on the island, and a successful winery was soon established.
Eventually, The Kelleys Island Lime & Transport Company would become the biggest supplier of limestone in the world and the Kelleys Island Wine Company one of the largest wineries in the US. But, after a century of prosperity, the limestone operation wound down and prohibition put an end to the winery, which ceased even its curtailed operations following a series of fires that destroyed the facility. Minor limestone mining still takes place on the island and a new, small-scale winery has been operating since the 1980s, but Kelleys Island was finally able to slow down and become the sleepy little vacation spot that we enjoy today.

