The Discovery
    In 1870, Dering Harbor was a pristine sheltered harbor surrounded on all sides by fields and forest. Other than the 100 or so families who lived on Shelter Island, making their living fishing and farming, no one had heard of it. By August 1874, this coast of Shelter Island, facing Greenport on the North Fork of Long Island to the north, had become a bustling family summer vacation destination. Two large family oriented hotels flanked the harbor and it was filled with yachts from Commodore Cornelius Vanderbilt’s destroyer sized North Star to small day sailors that could be rented from Island entrepreneurs. Dering Harbor was the jewel in the crown of two resorts which would cater to two historical phenomenon: family vacation hotels and the recreational use of sea faring craft. 
    Until the mid nineteenth century, there was not a middle class with enough discretionary income to seek recreational entertainment. Except for a few, everyone worked from dawn to dusk. Suddenly, for the first time in the memory of man, vast numbers of people could play. And, they wanted to take their families to beautiful places that would cater to their every need.  On top of this, since the early Phoenicians were seafaring merchants in the Mediterranean, going to sea was considered extremely dangerous: One did not take to the water without fear. At first, only the very wealthy took to yachting in their big vessels, but by the 1880's yachting was also a middle class sport.
    Because the railroad had come to Greenport in 1844, the same year, incidentally, the New York Yacht Club was founded, and New York City was now only two hours away on trains that traveled over 100 miles per hour, and steamboats from New England could ferry large groups of people safely and quickly across Long Island Sound from Boston and New London, Shelter Island was now easily reached for a day’s jaunt or for longer family vacations. It was only a matter of time before this beautiful island would be discovered by developers seeking sites for family hotels and yachtsmen looking for safe harbors in which to anchor and find nightly entertainments on shore.
    And that happened around 1870. Two choice pieces of land, both overlooking the beautifully protected Dering Harbor were available: the 300 acre estate of Squire Chase who had died 14 years before; and Locust Point, a 200 acre tract owned by Eben Horsford, a professor at Harvard University and heir to the Sylvester estate who believed that the Island’s economy would be greatly enhanced by hotel and land development. 
    In 1871, a group of Brooklyn developers purchased the Chase property and on May 11, 1872 incorporated as The Shelter Island Grove and Camp-Meeting Association of the Methodist Episcopal Church. The Association planned a camp meeting and vacation resort anchored by a large family hotel. There would be a wharf, bathing pavilion, camp tabernacle and restaurant. In addition, along the model of Weslyan Grove and Oak Bluffs on Martha’s Vineyard, they intended to sell lots to families for summer cottages. The Prospect House opened for guests in July 1872. 
    One month later, a group of developers from Massachusetts, led by Erastus P. Carpenter, purchased Locust Point. In December, a corporation was formed and Locust Point formally became Shelter Island Park.  Also planned was a large family-style hotel with residential lots surrounding it.  Mr. Carpenter was also the developer of Oak Bluffs, a residential community of substantial houses adjacent to the thriving carpenter gothic summer village of small gingerbread houses at Weslyan Grove. 
    The landscape designer for Oak Bluffs was Robert Morris Copeland. It was not long before Copeland, at the behest of Carpenter, was on Shelter Island planning both Shelter Island Park and The Heights.  It is thought that his original brief was to develop a lot plot and landscape design for the Park but was soon hired to do the same work for the Heights Association as their hotel was in full operation but they needed a plan for further development. 
    His plan shows many hundred of small lots for a virtual city for spiritual and recreational renewal, with avenues of houses along Chase Creek from Chequit Point to what is now the eastern portion of West Neck Road, and virtually covering all of the Goat Hill Golf Course. Luckily for the Island, just as Shelter Island Heights was beginning to be developed, the camp-meeting movement was slowing rapidly, and Copeland’s plan for development never reached beyond the area surrounding the Prospect Hotel and along Divinity Hill. Also to its advantage, potential summer residents did not want to build the little houses as conceived by the developers, and they bought multiple adjacent lots and built bigger houses. 
   Copeland's plans for Shelter Island Park were also quite ambitious, and  for a variety of reasons, perhaps expense as well as confusion over covenants in the deeds, fewer houses were built around the Manhanset House and those were also built on multiple lots.  What is now Dering Harbor remains the smallest village in New York State.