Dering Harbor’s Discovery Changes Shelter Island Forever Part 7 of 9 Compiled by Patricia Shillingburg

Gradual Maturity      For several generations, the activities surrounding the hotels dominated life on Shelter Island. The Prospect House in The Heights (1872 - 1942) and the Manhanset House in The Park (1874 - 1910) grew in fashion and activities until much of life on the Island revolved around the needs and recreational enjoyments of the summer visitors.  The presence of these grand hotels spurred the growth of other guest houses around the Island. These included the Chequit Inn (originally known as the Bay View House and owned by the Shelter Island Heights Association), the Shelter Island House, and the Oxford House. There were also boarding houses, such as Menantic Grove House, the Robin’s Nest on the Corner of Grand Avenue and Chase Avenue, and the Winyah on Chase Avenue. Local farming families also took in boarders. By the turn of the 20th Century, much of Shelter Island’s industry was focused on the tourists who found their social center in the amenities and activities surrounding Dering Harbor. Locals opened businesses to cater to the needs of the summer visitors, including Griffing and Young's who, for a time, owned the only building on what is now Bridge Street, a general store that “carried dress good, notions, household supplies kerosine, some canned staples, hats, lanterns -- altogether a thorough museum piece.” 1 Dawson’s Market, the Pharmacy, and, of course Conklin’s dock were centers of activity.   Transportation to the Island and on the Island itself changed dramatically to serve the needs of the summer visitors and eventually the Islanders themselves.      Stewart Herman explains: These changes inevitably brought still other changes to an insular community that had expanded very gradually over the last three hundred years, from one small family to about eight hundred permanent residents, all of whom lived frugally from the soil and the sea. Ferry service, for instance, took on a new significance. Less than thirty years before the building of the hotels, a young man named Jonathan Preston had made several efforts, none of them successful, to inaugurate a regular Greenport-Shelter Island-Sag Harbor service with sailing boats — the first six feet, the next eighteen feet, and the last twenty-three feet long. Those were the days when carriages went by raft and horses swam, tethered astern. A decade later, Captain Preston obtained a state ferry charter and built the first dock in Dering Harbor.      In the 1870s, thanks to the steam engine, more dependable ways of reaching Shelter Island, and filling its hotels, became possible. Train service from New York to Greenport was already excellent — two hours flat from Flatbush Station in Brooklyn. With the advent of the hotels, a triangular ferry service from Greenport to Prospect to Manhanset was instituted. The first vessel to provide this vastly improved service was the Cambria, a fishing boat converted to steam only a couple of years before; it was destined to ply the route for twenty years. It was owned and operated by Frederick Chase Beebe, an Islander, who after selling out in 1876 went into boat-building in Greenport. [With Capt. C. H. McClellan, head of the U. S. Life-Saving Service, he developed the famous Beebe-McClellan self-bailing, self-righting boat for rescue work from open beaches.] To supplement the train and ferry, the overnight steamers Escort and W. W. Coit brought whole households— families with servants—direct from New York City to Shelter Island with bag and baggage, horse and carriage, to spend the summer.      The next change, logically, affected Shelter Island’s roads. Hotel guests could not be expected to spend all their leisure time in rocking chairs on the broad piazzas. The owners of large yachts, whose handsome craft filled the harbor, were in a class by themselves; but even they enjoyed a change of pace, especially when becalmed. The Prospect House opened an Entertainment Hall near its beach with indoor games, a restaurant and an ice cream saloon. Manhanset had its Amusement Hall -- billiards, bowling, etc.-- next to the hotel. But all this was still not enough.     There were other things to be done and sights to be seen: for example, a 'plague' of tramps which overran the Island in 1877, or the annual gypsy caravan which arrived via the South Ferry and was quickly escorted to the North Ferry --not to mention the team of horses that met with a grisly accident in 1875 when they were caught in the turning blades of the old grist mill and ended, it was said, with their hooves in the air; or what was left of the Lookout Tower on White Hill after a bad storm demolished it that same year. Such things had to be witnessed at first hand as part of the summer’s souvenirs. Before the end of the first decade, a livery franchise was granted to a local entrepreneur, who supplied horses, both fast and slow, as well as ‘smart turnouts.’ Then a branch livery was set up near Prospect ferry slip—a regular rent-a-carriage, drive-it-yourself operation. Hence the need for more and better roads for enjoying scenic views not exceeded by any watering place south of Mt. Desert.      Those were the days before Shelter Island had highways. The approach to Manhanset on the landward-side, for example, was over a rough wagon road through fields and meadows which were well fenced in. Such barriers were annoying to sightseers, even after young volunteers had seized the opportunity of riding along to remove the bars—for a small tip of course. The first and almost the only public highway on the Island seems to have been the link between the South Ferry and Boisseau’s, which ran from Crescent Beach to Southold before the service to Greenport was inaugurated.