History of Hamilton House

The history of our Second Empire Victorian mansion began long before the entrance of its name-sake, Herbert Hamilton. The diverse and interesting history of this home has been traced back to when the land belonged to the government. Dr. James Trippe purchased the land from the government on March 25, 1841. After the land passed through several hands, Dr. Greenman, the local dentist purchased the land in 1861. The home is said to have been completed in 1868. This is assumed due to a significant tax increase on the property in that year. Dr. Greenman and his wife, Elizabeth, lived in the home until 1880.

The Van Gieson / Posey family purchased the home on August 20, 1880. Van Gieson’s daughter, Sarah was married to Oliver P. Posey (initials in the entry hall window). In 1881 major additions were made to the home. Four rooms were added to the east side of the home, the bay windows were added or enlarged, doors and windows were upgraded, Queen Ann style porches were added and the main stairs were changed. Sarah gave art lessons from the home. Her hand painted tiles can still be seen inlaid into the woodwork of the grand staircase.

The home changed hands again several times before Herbert Hamilton purchased the home on October 19, 1903 for $5,000. The Hamilton’s were the first Whitewater natives to own the home. Herbert lived here with his sister Ella, a librarian at the Whitewater library for 25 years. After the death of the last Hamilton, the home was sold in 1950.

Since 1950, the home suffered greatly. It changed hands many times, almost being torn down twice to make way for a library parking lot, serving as a rooming house, Sorority, Fraternity, doll museum, antique store, office building, and finally a family residence and Bed and Breakfast. September 29, 2000, the current owners, the Fleming / Witham families, purchased the inn with the intent of returning it to its original grandeur and operating a luxury bed and breakfast. A year long construction project was begun upgrading the amenities including additional baths, opening the parlors for guests’ use, and redecorating. After a season of operation, another construction project was started to build out a cozy, three bedroom innkeepers’ quarters in the basement. This enabled the opening of two more rooms. The Hamilton House Bed and Breakfast now boasts eight guest rooms, all with private baths and most with fireplaces and/or whirlpool tubs.

After moving in, the innkeepers began to hear rumors of the existence of secret tunnels leading to other homes and the train depot. These tunnels are believed to be a part of the Underground Railroad. We anxiously await further investigations and stories that gradually find their way to us as the mysteries of Hamilton House unfold.

Hamilton House Bed & Breakfast

Premier Lodging in the Southern Kettle Moraine State Park