The schooner H.L. Whitman was launched into the Milan Canal on the Huron River from the shipyard of Salmon Ruggles in Milan, Ohio on June 23, 1856. The H.L. Whitman was named for banker Henry L. Whitman of Cleveland. It was described as having one deck and two masts, with square stern and plain head, and H.L. Whitman was commanded by Captain John Jennings. It is likely the Panic of 1857 curbed the H.L. Whitman for much season, as few records of the ship’s movements could be located in contemporary newsprint. By the beginning of October 1857, Salmon Ruggles decided to part with his share of the vessel, and eventually Captain L.L. Phillips became the vessel’s new Master and Milan, Ohio became its new homeport.

On September 2, 1859, the ship was down bound through the Welland Canal enroute to Oswego. It arrived at Chicago from Oswego 2,230 barrels of salt twenty days later. Additional trips to Oswego were made in October and November. On the up bound leg of her November trip, on November 16, H.L. Whitman went ashore about six miles west of the Genessee River on Lake Ontario. The ship sailed on a compass bearing northwest from the Sodus Light on a course toward Toronto. More than a dozen vessels had gone ashore there within a ten-year period, and in every instance, the disaster was attributed to defects in the compasses. The tug Page was working nearby to remove the schooner Andover that stranded there a week earlier, and went to H.L. Whitman’s assistance. The Whitman was pulled free and continued on its voyage.

On April 19, 1861, H.L. Whitman was up bound with its first cargo of the season when it stranded at the foot of Grassy Island in the Detroit River. Captain L.L. Phillips was able to kedge the ship off without damage.

H.L. Whitman cleared the Port of Oswego for Sandusky with 50 tons of coal on April 13,1863. Upon its arrival at Sandusky on 25 April, the ship's enrollment document was surrendered and a temporary enrollment taken out for a change in managing owner, owners, and districts. As Chicago was now the home of both partners, the Whitman's homeport was changed to that city. The ship received a B1 insurance rating, as it was described as “rather flat”, and consequently was valued at $6,500. On 26 April 1865, H.L. Whitman’s enrollment was surrendered at the Port of Chicago for change of owners. Captain Edward Comerford of Chicago came into command and became ¼ owner. Comerford, a native of Ireland, had sailed the Great Lakes for twelve years, but H.L. Whitman was his first command. At the time of transfer of ownership, the vessel was re-measured and assigned an official number.
On the night of October 11, 1869, while bound from Oconto, Wisconsin to Chicago with a cargo of lumber, H.L. Whitman’s Captain E. Finn navigated too close to Racine’s North Point, now known as Wind Point, and struck the reef. The deck load was thrown overboard in an attempt to lighten the vessel, but the ship filled with water and sank. A steam pump was requested to be sent up from Chicago the next day but it was delayed in arrival. A south wind for the next three days created heavy seas that pounded the vessel on the reef. On October 14, the tug Mosher arrived from Chicago towing the schooner John S. Wallace as a lighter. After only one day of work on the stranded vessel, Captain Brewster of the Mosher reported that the H.L. Whitman was too far gone, and would be left to go to pieces. He salvaged its sails and returned to Chicago.

On 14 July 1870 H.L. Whitman’s enrollment was surrendered at the U.S. Customs Office in Chicago. John S. Wallace had a B1 insurance rating, valued at $6,000 and insured by the Republic Insurance Co. of Chicago. The company paid $5,000.
The remains of the schooner H.L. Whitman lie 0.13 miles off shore north of North Bay, Wisconsin, in the waters of Lake Michigan. The vessel sits 0.94 miles southeast of Wind Point, and lie perpendicular to the shore, resting in 10 feet of water, with the extent of its bow and stern missing. The wreckage rises 3.0 feet to 5.0 feet off the bottom of the rocks and silt within the bay. From just below the turn of the bilge down, the floors and frames of its lower hull remain relatively intact on an even keel. The wreck’s shallow location near the surf zone has contributed to the lack of mussel growth on the remaining timbers. Though all of its upper deck works, rigging, hull components, and machinery were salvaged after sinking or were broken by years of wave and ice action along the shore, major structural components of the vessel remain extant, including its keel, keelson, and mast steps.