Caroline County native Captain Caleb Clark Wheeler was a 19th century hero of individual enterprise.  After successfully operating sailing schooners between the Choptank and Tuckahoe and Baltimore, Wheeler established the only steamboat line based on the Eastern Shore.

During the 1880s and 1890s, the Wheeler Transportation Line, with headquarters in Hillsboro, served lower Choptank and Tuckahoe River landings with the elegant Easton and Chesapeake, and the beloved Minnie Wheeler.

C.C. Wheeler’s personal style of leadership and service to Tuckahoe and Choptank farmers and townsfolk helped him compete against larger steamboat companies and remain independent until his untimely death in 1899, at age 59.

On this easy river trip, you can explore the ruins of Wayman Wharf, which served as shipping point for the town of Hillsboro. Examine ruined wharf cribbing and the wreck of a river barge.

Imagine the 130-foot Wheeler Line steamboats unloading cargo and passengers, then turning around in this narrow stretch of river for the return to Baltimore. Notice how river siltation has filled the channel here, and consider its impact on river transportation when steamboats were the lifeline between country and city.