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In 1877, Wheeler purchased the wooden freight and passenger steamer Raleigh for use on the Baltimore to Choptank-Tuckahoe route. But Raleigh proved unstuitable for Wheeler’s primary enterprise of hauling grain, and he sold the vessel within a year. Wheeler replaced Raleigh with Ruggles,
a 124-foot screw steamer. By 1880, Ruggles was making two trips each week between Baltimore and Hillsboro.
Wheeler also chartered other steamboates, including Conoho, Hamilton, Meteor, and John E. Tygert, to carry produce to Baltimore during the busiest times of the harvest season.
Ruggles provided passenger service twice weekly between the Tuckahoe and Baltimore, leaving the city every Saturday and Wednesday at 7 p.m. and arriving at Hillsboro at 9 a.m. the next day. She remained overnight and returned Monday and Thursday at 10 a.m.
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