The two masted wooden schooner D.O. Dickinson also known as the Daniel O. Dickinson was built in Milwaukee, Wisconsin in 1854 by James M. Jones. In September, 1862 the Dickinson received an overhauling and rebuilding by Wolf & Lawrence in Milwaukee. On November 13, 1854 the Sandusky collieded with the D.O. Dickinson.

Last Document Of Enrollment Surrendered: Chicago: 12/9/69: "Vessel Lost".
The D.O. Dickinson sailed from Oconto, Wisconsin on October 7, 1869 with a cargo of lumber destined for Chicago delivery. While negotiating the unmarked Strawberry Channel (on October 8th), the vessel ran ashore upon the southeast end of Chambers island often referred to as Strawberry Reef. Captain William Cardwell and crew of four took to the yawl, went to Menominee, Michigan and obtained the services of the tug Reindeer, and then returning to the stricken schooner. Because of the high winds, neither the tug nor another scow could closely approach the Dickinson to attempt to pull her off. The D.O. Dickenson was broken amidships during the continuing gale on the 9th and 10th of October. "At 11 a.m. on the 16th, the wind having risen again at midnight, both masts went by the board; her decks burst open, and floated away. She then finally, washed over the top of the reef, and disappeared from view..." from a letter to the Chicago Tribune.
The abandoned cargo was eventually recovered, but $9,500 worth of insurance was paid on the lost hull. The overall value of the ship and cargo was estimated to be $21,000.
October 21, 1869. "Gone to Pieces--the propeller G.J. Truesdell, which touched here yesterday, on her way to Chicago from Green Bay, had on board the outfit of the schooner D.O. Dickinson, recently wrecked upon strawberry shoal. Clerk Wilkins informs us that the vessel is completely broken up, and but little remains visible." Milwaukee Sentinel, October 21, 1869.