In the late 1800s, Osterville emerged as a destination. People would arrive by stagecoach and train to stay at the many inns and lodges around this coastal village. West Bay Inn and East Bay Lodge became social gathering spots where people would stay for weeks or months. Churches, family markets, and the library lined Main Street. In 1914, the Crosby family designed a special racing class of boats,the Wianno Seniors. The Wianno Senior Knockabouts were commissioned by the wealthy families that founded the exclusive clubs Seapuit, Osterville-Wianno, and Oyster Harbors; Osterville-Wianno and Oyster Harbors are still known for their golf courses and are enjoyed by residents and visitors today.
