Highland Drive climbs and winds up an inclined bluff, with eruptive outcroppings along the way, to culminate in Conanicut's Southwest Point. Depending on orientation, the topography offers perches for houses with precipitous views down into Mackerel Cove between Conanicut and Beavertail and off to the ocean, or up the bay and across its channels, or any combination of these. No area in the state offers more varied panoramic water views in such proximity. Most travelers by car (in summer especially) will not see these hideaways, except in fragmentary glimpses and a few distant views; more is visible from the water. Still, even from a car in summer one senses the extraordinary quality of this place. Most of the older houses are medium-to-large shingle houses, luxurious but unostentatious. The late twentieth century brings the Shingle Style revival to the area, generally in less vernacular-inspired, showier examples, mingling much from intervening modernism with late nineteenth-century sources.
Like its contemporary at the northern tip of the island, Conanicut Park, Ocean Highlands too had been a farm, 240 acres, predominantly for sheep, as one might expect of such a tumultuous landscape with such buffeting weather for much of the year. Unlike Conanicut Park, however, Ocean Highlands was intended for those ranging in wealth from the well-to-do to the outright rich who, for reasons of economy or lifestyle, preferred its rustic and isolated exclusivity over Newport. The area was opened for development with the founding in 1874 of the Ocean Highlands Company, headed by Philip Caswell, Jr., as the prime mover for a group of investors. The depression in the 1870s and the remoteness of the site delayed any considerable building before the next decade, although Caswell gave a site to the Philadelphia marine painter, William Trost Richards, in the 1870s in the hope of inducing others to come. Richards had owned a cottage in Newport, but as it became increasingly built up, he sought a more isolated place for inspiration.
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