Charles L. Cromwell served as the RFD mail carrier for 30 years on Westport Island beginning in 1905. He boated to Wiscasset where he picked up and sorted the mail, carried it to his boat, rowed back across the harbor, tied up, and carried the mail bags up the hill through the woods to his waiting horse and buggy. He got a car in 1923, but he could only use it in the summer.

Sometimes, Cromwell made several trips to accommodate island patrons who asked him to bring back groceries or a bag of grain. For many years, he had to make the return trip to Wiscasset after traveling 25 miles around the island collecting outgoing mail as he made his deliveries.