The BERTIE's connection with the ELLA, the KALULA, the CHOWAN, the PLYMOUTH, and the S.A. McCALL
Beginning in March 1873, Captain Wilbur F. Askew and Purser Edward Solon Askew started hauling freight and passengers with the BERTIE. Richard Askew, proprietor of the Askew family store in Windsor, was the steamer's agent. He organized incoming guano shipments and outgoing freights to be transferred to the steamer ELLA, the BERTIE's connection at Plymouth. Apart from the steamer's regularly scheduled trips, the brothers also planned excursions to the Albemarle Sound fisheries and to Nag's Head. The BERTIE operated on a Monday/Wednesday/ Friday schedule between Windsor and Plymouth carrying passengers, freight, and the U. S. Mail. Its printed schedule in the newspaper apprised travelers of its departure and arrival times. After departing Windsor at Noon, the steamer traveled down the Cashie River stopping at the river landings on its way towards Plymouth, where it arrived around four o'clock P. M. Once the Plymouth freight was landed, Wilbur F. Askew or Edward Solon Askew directed the loading of the return freight in anticipation of an eight o'clock P. M. departure for Windsor. After departing Plymouth, the steamer headed upstream for Windsor in time to make its published Midnight arrival time. The Askew brothers advertised that their steamer was built for passenger comfort and even included staterooms for the traveling public.

In Plymouth, the BERTIE's passengers continuing their journey boarded the Albemarle Steam Navigation Company (ASNC) steamer ELLA. (Windsor Albemarle Times, 24 July 1874) The ELLA was a 323 ton wooden side-paddle steamer measuring 148 feet 9 inches long, 24 feet 9 inches wide, with a 8 foot depth of hold. The BERTIE connected with the ELLA until 31 March 1875, when the ELLA left service. (Richard E. Prince, Norfolk Southern Railroad, Old Dominion Line, and Connections (Millard, Neb.: Richard Prince, 1972, 205)

After the ELLA's retirement, the BERTIE connected with the steamer CHOWAN at Plymouth. The CHOWAN operated as part of the Blackwater Line, which connected Franklin, Virginia, Edenton, and Plymouth. Built in 1875 in Wilmington, Delaware, the iron-hulled side-paddle steamer was 150 feet long, 28 feet five inches wide with an 8 foot 2 inch depth of hold. Roughly the same length as the ELLA, the CHOWAN's 459 ton cargo capacity was 139 tons greater than the ELLA's because of the new steamer's greater breadth. (Richard E. Prince, Norfolk Southern Railroad, Old Dominion Line, and Connections, 205)The CHOWAN's published schedule began with the steamer's departure from Franklin on Monday, Wednesday, and Friday after the arrival of the mail train from Portsmouth, Virginia. The CHOWAN reached Edenton at four o'clock P. M. and Plymouth at six o'clock P. M. Northbound Passengers and freight from the BERTIE boarded the CHOWAN for the evening trip to Franklin. (Windsor Albemarle Times, 17 December 1875) The railroad connection in Franklin gave passengers access to the large northern cities through rail or the Chesapeake Bay steamer lines.

During the 1880s the BERTIE's schedule altered significantly as the steamer came under new ownership. Charles Harden bought out Edwards Solon Askew's share in the late 1870s and by 1882-1883 Harden had also acquired Wilbur F. Askew's share. Now navigating as the Cashie Steam Navigation Co., the BERTIE made daily trips between Windsor and Plymouth. On everyday except Sunday, the steamer left Windsor between four and five o'clock A. M. and arrived in Plymouth at half past nine A. M. to connect with the Steamer PLYMOUTH running to Edenton. Passengers, the U. S. Mail, and freight were exchanged. The BERTIE waited in Plymouth for the return of the PLYMOUTH before departing again for Windsor where it arrived at half past eight P.M. (Edenton Albemarle Enquirer, 15 July 1886) Although Wilbur F. Askew no longer owned the BERTIE he served occasionally as the steamer's captain until October 1888 when he took charge of the steamer S. A. McCALL owned by the Jamesville and Washington Railroad Company.