In 1847, George Law and Daniel Drew formed a partnership, and established a line of steamers between New York and Stonington, for the purpose of connecting with the railroad from the latter place to Boston.  The “Oregon” and the “Knickerbocker” were placed on the route, and the enterprise proved a success.  Mr. Drew and Commodore Vanderbilt secured a sufficient amount of stock in the railroad to give them a controlling interest in it, and by the year 1850 the Stonington Steamboat Line was firmly established.

When the Hudson River Railroad was opened, in 1852, it was confidently expected that the steamboat trade on the river would be destroyed, and the friends and enemies of Mr. Drew alike declared that he might as well lay up his boats, as he would find it impossible to compete with the faster time of the railroad.  He was not dismayed, however, for he was satisfied that the land route could not afford to carry freight and passengers as cheap as they could be transported by water.  He knew that it would only be necessary to reduce his passenger and freight rates below those of the railroad, to continue in the enjoyment of his immense business, and his faith in the steady expansion of the trade of the city induced him to believe that the time was close at hand when railroad and steamers would all have as much as they could do to accommodate it.  His views were well founded, and his hopes have been more than realized.  The river trade has steadily increased, while the Hudson River Railroad is taxed to its utmost capacity to accommodate its immense traffic.

In 1849, Mr. Drew, in connection with other parties, bought out the Champlain Transportation Company.  This corporation had a capital of one hundred and fifty thousand dollars, and ran a line of five steamers from White Hall to the Canada end of the lake.  The new proprietors ran the line seven years, and in 1856 sold out to the Saratoga and White Hall Railroad Company.

As a steamboat manager, Daniel Drew has few equals and no superiors.  His ventures on the water have all been crowned with success, a result due entirely to his judicious and liberal management His employes are chosen with the greatest care, and generally remain with him during their lives.  He is very liberal in his dealings with those who serve him faithfully, but will not tolerate a single careless or incompetent man, however unimportant may be his position.  The steamers owned by him are almost entirely free from accidents, and such misfortunes as have befallen them have been those against which no skill or foresight could guard.  He refuses to insure his boats, holding that care and prudence are the best safeguards against accidents, and thus saves half a million dollars.  When the “Dean Richmond” was run down by the “Vanderbilt,” a year or two ago, he lost nearly three hundred thousand dollars.  He paid every claim presented by shippers and passengers, as soon as made, without submitting one of them to the adjudication of the courts.