During its many years, the Hotel Hamilton hosted meetings, wedding receptions and society events. In 1948, the hotel welcomed Coach Earle Neale and the Philadelphia Eagles football team of the National Football League when they arrived for a week of training at Walsh Field. The Eagles had previously trained in Two Rivers during 1941 and 1942.

During the 1800s until the early 1900s, Kingsbridge was a booming little crossroad village. In a 1997 Pinecrest Spirit article it is said that in 1880 Kingsbridge had a population of 65 people. As settlers came to Manitowoc County, more and more little crossroad villages like Kingsbridge started to form. Crossroad villages usually included a blacksmith shop, saloon, post office, cheese factory and in many cases a church and school. Kingsbridge was not a typical crossroads village, however.

The Windiate House became a popular place for many prominent businessmen. Officials of the Goodrich Line made it their headquarters and Thomas Windiate also owned his own stagecoach line. The hotel featured a dining room, bar, and a pool room. The dining room was a popular site for high scale parties throughout the 1860s and 1870s. In 1899, rates were $2 per day for “first class accommodations for the traveling public”.