Beginning in 1880, the Eastern Steamship Company carried passengers and freight from Bath to Boothbay Harbor stopping in several island ports on the way. Westport had two landings, the Upper Landing near Hell Gate where passengers were left, tide permitting, and the Lower Landing or Junction where passengers and freight were transferred to smaller boats. This route is closed in winter by the ice.
During the season the steamer Wiwurna was making as many as 3 round trips a day in the very active years before WWI. The steamers Nahanada and Samoset also served this route. Two elegant new steamers the "Westport" and "Southport" were built for the route and put in service in 1911, but unfortunately they proved too large (120 ft.) for the narrow waterways. They were replaced by the Islander and the Virginia. These ran thru the 1920's.
Steamer - "Westport"
Steamer - " Nahanada"
Ice-free year-round service was provided on the Main Sheepscot River for many years by the steamer Winter Harbor. Purchased by Captain Frank Rowe in 1908, he made arrangements with the Post Office Dept. to carry the mail from the railroad at Wiscasset to Boothbay harbor and the Islands.
Steamer "Winter Harbor"
Capt. Rowe arranged with Westporter Author Tarbox on the East Side at Swanton Cove to pick up passengers and freight in his skiff on a regular basis, thus "Tarbox Landing" without any wharf, cost 10 cents each. This arrangement continued for many years. Besides passengers, the freight of all kinds might often include ice cream for the regular Westport Saturday Night dances in the Town Hall. The boat made two round trips a day, making four possible calls a day at Westport. Aurthur Tarbox died in 1928. The Winter Harbor made it s last run in 1932.