In 1712, the Gaylord couple came to New Milford, Connecticut, which had been settled only five years previously. Their house stood on the corner of Main and Elm Streets. For a time he kept a tavern there in addition to doing his regular work as a surveyor. He did a lot of surveying for the State, laying out town boundary lines, and it was, no doubt, on one of these surveying trips that he became impressed with the large areas of level land several miles north of the New Milford village, just north of the straits on the Housatonic River. He began taking title to parcels of it, and soon owned a large part of the valley. To ensure the good will of the Native Americans living in the area, he also bought it from them, giving, according to legend, a horse, a mule, and a two-wheeled cart.