The mean elevation is about 1,100 feet above the sea. The highest point being Tip-Top, 1,310 feet, and the lowest point 620 feet. The Hill is characterized by its immediate and abrupt rise above surrounding localities, being from 500 to 830 feet above the village of Pawling, in which the waters divide for the Hudson and Housatonic Rivers. On its highest hill rises the brook which becomes the Croton River. From almost the whole length of Quaker Hill road one looks off over intervening hills to the east for twenty-five miles, and to the west for forty miles to Minnewaska and Mohonk; and to the north fifty and sixty miles to the Catskill Mountains.

One's first impressions are of the green of the foliage and herbage. The grass is always fresh, and usually the great heaving fields are mellowed with orange tints and the masses of trees are of a lighter shade of green than elsewhere. The qualities of the soil which have made Quaker Hill "a grass country" for cattle make it a delight to the eye. Well watered always, when other sections may be in drought, its natural advantages take forms of beauty which delight the artist and satisfy the eye of the untrained observer.

The Hill is a conspicuous plateau, very narrow, extending north and south. It is "the place that is all length and no breadth." Six miles long upon the crest of the height runs the road which is its main thoroughfare, and was in its first century the chief avenue of travel. Crossing it at right angles are four roads, that now carry the wagon and carriage traffic to the valleys on either side; which since railroad days are the termini of all journeys. The elevation above the surrounding hills and valleys is such that one must always climb to attain the hill; and one moves upon its lofty ridge in constant sight of the distant conspicuous heights, the Connecticut uplands east of the Housatonic on one side, and on the other, the Shawangunk and Catskill Mountains, west of the Hudson, all of them more than 25 miles away.

Unsheltered as it is, the locality is subject to severe weather. The extreme of heat observed has been 105 degrees; and of cold—24 degrees.

Quaker Hill possesses natural advantages for agriculture only. No minerals of commercial value are there; although iron ore is found in Pawling and nearby towns. On the confines of the Hill, in Deuell Hollow, a shaft was driven into the hillside for forty feet, by some lonely prospector, and then abandoned; to be later on seized upon and made the traditional location of a gold mine. The Quaker Hill imagination is more fertile and varied than Quaker Hill land. No commercial advantages have ever fallen upon the place, except those resultant from cultivation of the fertile soil in the way of stores, now passed away; and the opportunity to keep summer boarders in the heated season.

Interest which attaches to Quaker Hill is of a three-fold sort: historical, scenic and climatic. The locality has a history of peculiarly dramatic interest. It is beautiful with a rare and satisfying dignity and loveliness of scene; and it is the choice central spot of a region bathed in a salubrious atmosphere which has had much to do with its social character in the past, and is to-day very effective in making the place a summer settlement of New York people. The population is increased one hundred per cent. in the summer months, the increase being solely due to the healthful and refreshing nature of the place.

The history of the locality is associated with the quaint name, "The Oblong." This was the name of a strip of land, lying along the eastern boundary of New York State, now part of Westchester, Putnam and Dutchess Counties, and narrowing to the northward, which was for a century in dispute between New York and Connecticut.

There had been a half century in which this was all disputed land, between the Dutch at New York and the English in New England. Then followed a half century of dispute as to the boundary between sister colonies, which are now New York and Connecticut. As soon as this was settled in 1731 the immigration flowed in, and the history of Quaker Hill, the first settlement in the Oblong, begins. It was granted to New York; and in compensation the lands on which Stamford and Greenwich stand were granted to Connecticut after a long and bitter dispute. The end of the dispute and the first settlement of the Oblong came, for obvious reasons, in the same year. The first considerable settlement of pioneers was made at Quaker Hill in 1731, by Friends, who came from Harrison's Purchase, now a part of Rye.[3]

The historical interest of the locality dwells in the contrast between the simple annals of Quakerism, which was practiced there in the eighteenth century, and the military traditions which have fallen to the lot of peaceful Quaker Hill. The "Old Meeting House," known for years officially as Oblong Meeting House, experienced in its past, full of memories of men of peace, the violent seizures by men of war. That storied scene, in the fall of 1778, when the Meeting House was seized for the uses of the army as a hospital,[4] has lived in the thoughts of all who have known the place, and has been cherished by none more reverently than by the children of Quakers, whose peace the soldiers invaded. Both the soldier and the Quaker laid their bones in the dust of the Hill. Both had faith in liberty and equality. The history of Quaker Hill in the eighteenth century is the story of these two schools of idealists, who ignored each other, but were moved by the same passion, obeyed the same spirit. It is said that a locality never loses the impression made upon it by its earliest residents. Certain it is that the roots of modern things are to be traced in that earliest period, and through a continuous self-contained life until the present day.

In the eighteenth century Quaker Hill was the chosen asylum of men of peace. Yet it became the rallying place of periodic outbursts of the fighting spirit of that warlike age; and it was invaded during the great struggle for national independence by the camps of Washington.