The building was constructed between 1860 and 1880 to be used as a boarding house. The land was purchased from the Winnebago Indians some years earlier. Its original use was a rooming house and stables for the Stamm House Stage Line. Ye Olde Tavern opened in the 1880s before becoming the Club Tavern in 1921. The tavern never closed during Prohibition, remaining open throughout that entire era.

The biggest bar in Middleton, with an excellent family restaurant attached. Live music Wednesday through Saturday. Whether it’s eats or drinks, you’ll find what you’re craving at the
Club. Groups welcome. Motorcoach parking available.

In 1855 a building located here contained a hotel, a saloon, and on the second floor, an opera house. The “Opera House” was a large
hall with a platform stage. Events held here included medicine shows, masquerades, holiday dances, political rallies and graduations. The original building burned to the ground in the 1900 fire. A smaller structure replaced the original and was known as the Elk’s Hotel. It is now remodeled and serves as apartments.

Built in 1856 as a General Store known as “The Friendly Store,” farmers exchanged eggs and butter for groceries, clothing, yard goods, fencing materials and machinery. A tavern was located in the basement.

The depot was originally built in 1856 as part of a new railroad line being built from Madison to Mississippi River shipping docks in Prairie du Chien. The Middleton Station brought immediate changes, such as allowing farmers a means of transporting their crops to distant markets. In 1895, the station burned to the ground, and Chicago, Milwaukee and St. Paul Railroad rebuilt the structure as a late Victorian-style depot. The station remained active as a passenger station until 1960 and a freight depot until 1975. Today, this building, located on the National Registry, is a visitor welcome center housing the office of the Middleton Tourism Commission.

This building was Middleton's first Post Office, located outside of a private home, received mail by train. The mailboxes were on one side of the building, and on the other, stationery and confections were avilable, including ice cream during the summer. The upstairs of the building housed the first telephone company and Middleton's library. Today, it's home Villa Dolce. 

This is the former site of the American House Hotel, built between 1867 and 1870. The hotel's restaurant was so famous that people came from Madison by train to eat here. Especially popular were the Sunday chicken dinners for 25 cents!

Built in 1847, as Middleton's first official inn. For a time, it housed the Post Office for Pheasant Branch and had its own wine cellar. During the Civil War it was thought to be a station on the Underground Railroad, aiding escaping slaves to the North. Today, it is a popular restaurant.

Dine in an 1847 Stagecoach Stop and Tavern. Fine wines, Fish Fry and Sunday Brunch.

Built in 1853-1855 by T.T. Whittlesey, the house originally had 19 rooms. Mr. Whittlesey was a former member of Congress and a probate judge and was very influential in the development of Pheasant Branch and the Middleton area. On the first plat of Middleton, the roadway that is currently University Avenue was called Whittlesey Street.

The historic Wolf House was built in 1868. The structure was saved from burning down in a 1900 fire by removing the home's carpeting, taking it up onto the roof and keeping it wet by bucketing water on it. The present garage was once a summer kitchen. The house was modernized in 1938 and is now privately owned.