Cornelius Vanderbilt a business partner and friend of Drew made a challenge to race her against his own ship Traveler, which was serving the New Haven to New York route.

However as the vessels turned a stake boat at Ossining the Oregon pulled half a length ahead.

Cornelius Vanderbilt, who had taken the wheel, took the turn too quickly and over shot resulting in a small collision, which severely damaged the Oregons wheelhouse.

With fifteen miles to go, the tide in running south in favour of both, the Oregon ran out of coal and the crew started to feed the boilers with any wood to hand, burning furniture and the like.

One year later in 1848 Drew bought the “Oregon” from Law, for use on the Hudson River, taking her off the Stonington run.