he Inn was completed in 1893 by carpenter (and later the first Superintendent of Streets for The Town of Lunenburg) Reubin A.Conrad as a home for his new bride and himself. In 1913 the building was purchased by blacksmith George W. Hamm and his wife Sophia from the Conrad's heirs. In 1924 Sophia Hamm opened her home to paying guests as The Hillside Hotel, thus commencing a long history of providing hospitality and accommodations to the traveling public that continues to this day. Located beside the new train station opened in 1923, many of the first guests arrived by train with the tracks running between the two buildings. During the infamous rum running during prohibition, it is rumoured that Joseph Kennedy, father of US President John F. Kennedy, was a frequent guest at The Hillside Hotel.
Operating until October 1979, The Hillside Hotel gained a reputation of serving wholesome home cooked meals and comfortable lodgings to both travelers and Lunenburgers alike. In 1987 the building was rescued from a period of disrepair, restored into the condition befitting a registered heritage property and reopened as The Lunenburg Inn.