In 1830, he decided to leave North Carolina and try his fortune in the West. A preliminary tour of observation brought him to Cleveland, then lively with business, and more lively still with expectancy of business to come from the completion of the canal, then in partial operation. Like many who preceded, and more who followed him, Mr. Winslow was struck with the natural advantages of Cleveland and concluded to try his fortunes here. The site of what is now known as the "Winslow warehouse," on the river, was owned by C. M. Giddings and Captain Belden, and a building was then in course of erection on it. Mr. Winslow purchased the property. He had strong faith in the growth of the city, but others did not have it to the same extent, and he was strongly urged not to attempt business so far down the river, where it was impossible that trade would ever reach him. Immediately on concluding his purchase, he went to the eastern cities, where he purchased a large stock of teas and groceries, which he sent with his son, N. C., to Cleveland in the Fall. The stock arrived in December and was at once opened on Superior street, opposite Union lane. In the following May, Mr. Winslow followed with his family, purchased a lot on the south-east corner of the Public Square, and contracted with Levi Johnson for the erection of the house that was occupied by the Winslow family until the death of Mr. Winslow. Unlike most of the early settlers in Cleveland, Mr. Winslow came with capital to invest at once in business, and by prudent management and far seeing enterprise that capital rapidly increased. He soon became agent for a line of vessels between Buffalo and Cleveland, and also of a line of canal boats. The first step toward his own shipping interests here, which subsequently assumed such proportions, was commenced by building the brig North Carolina. A few years later he was interested in building the steamer Bunker Hill, of 456 tons, which at that time was considered a very large size. To these were added, by himself and his sons, so many other lake craft that the family ranked among the foremost, if not the very foremost ship-owners on the chain of lakes, their sail vessels, propellers and steam-tugs being found everywhere on the western lake waters. In 1854, Mr. Winslow retired from business, leaving his interest to be carried on by his sons, who inherited their father's business qualities. In his retirement, as in his active business life, he enjoyed the friendship of a very large social circle, to whom his frank, generous manners, warm attachments, and spotless honor commended him. He was a favorable specimen of the old school gentleman, warm and impulsive in his nature, quick to conceive and prompt to act, cordial in his greeting, strong in his attachments, and courteous to all.