Some idea of the bucolic nature of the place that would become Woodside can be seen in descriptions of an ancient central landmark, a great chestnut tree. The tree was hundreds of years old when it finally came down in the last decade of the 19th century. It stood on high ground near a junction of three dirt roads and "was of great diameter, some 8 or 10 feet"—perhaps 30 feet in circumference. Its size and central location made it a natural a meeting place, a surface on which to tack public notices, and strategic point of considerable military significance during the Revolutionary War. A 19th-century antiquarian wrote of the great tree as it stood during the American Revolution and in doing so named the families of the local landowners: Around the roots of the old tree were the huts and stables of the cavalry: with a number of settler's huts ranged in woods... Great festivities too were constant in the spacious rooms of the old Moore house, during the winter months when the snow was deeper and the frost more cold than now-a-days. To the streaming lights from the ball room, and the lanterns hung on the trees, were wont to assemble the gay sleighing parties from the Sacket Sackett, Morrell, Alsop, Leverich and other houses; for the soldiers were all over and had come to Newtown to recruit refresh and restore themselves after the yearly campaigns... Is there any relic more associated with Newtown the town in which the village of Woodside would come to be located than its old chestnut tree?... it not been for two centuries the "Legal Notice" centre of Newtown, for all vendues, real estate transfers, town meetings, lost "creeturs" and runaway slaves?