Tuckahoe River Trip - C.C. Wheeler Passage

Caleb Clark Wheeler was born in 1839 at Gilpin Point in Caroline County. At age 12 he began work as a cook on a sailing schooner that shipped goods and passengers between the Choptank and Baltimore. By age 18, he was a schooner captain, and at 21, he was part owner of the schooner John Nichols.

Wheeler could not read or write, but he had sharp business acumen. He opened a general store at Gilpin Point in 1862, at age 22, and served as middleman between Choptank River farmers and Baltimore merchants. He also married at this time.  Wheeler moved his business from Gilpin Point to Hillsboro in about 1870.

After his move to Hillsboro, Wheeler began to specialize in shipping grain.  He had a 76-foot schooner, named the C.C. Wheeler, built at St. Michaels in 1872. He also purchased two or three second-hand sailing vessels, including the two-masted schooner Dexter built by Satterfield and Moore in Greensboro. Dexter was about 20 years old when he bought her in 1891.  He kept Dexter less than two years.

Wheeler Transportation Line maintained an office and granary at Hillsboro Wharf.  Grain and passengers had to be carried from Hillsboro to Wayman Wharf, two miles downriver, on barges or scows.