The Exchange Hotel was the first hotel in Oregon, which was built in 1845 by Egbert Bennett and called the Oregon Exchange. It was located at 112-116 Janesville Street. It also served as the Post Office. This business failed and was purchased by Richard Chandler and became the Chandler House.
The Chandler Hotel was a booming business! It was reported that on some days 150 pounds of meat were consumed. One day in the 1880’s, local butchers, Doolittle and Hanan, supplied the hotel with 400 pounds of meat.
In 1885, the hotel burned down, and later again in in 1898, Charles W. Netherwood built the present Netherwood block.
Another early hotel, the Oregon Hotel, was located near the railroad depot. THe site was later home to the Allen Lumber Co and is now the Oregon Area Historical Society and Museum. The primary customers were the salesmen. Customers arrived by train and stayed for a few days to take orders from local merchants. This hotel was also the victim of fire and burned down in May of 1906. The fire bell went off in the middle of graduation ceremonies at Cronk’s Opera House. The graduation ceremony was put on hold, as the fathers, grandfathers, and others dealt with the fire.
“A deal was consummated Monday whereby W. N. Gillette becomes the owner of the old hotel near the depot, recently used as a sale barn. C. E. Robinson, who owned this property, takes a residence in Stoughton. Mr. Gillette will wreak the building and build two modern residences in the near future.”
A third Hotel was the Grand Central or Portland Hotel. This is the present site of Madsen Park. Originally on this site was a home owned by John D. Tipple and later owned by J.P. Main. The house burned in 1873. The Grand Central Hotel was built between 1880-1883.
In the early days, this hotel was managed by the Monks. They had managed the Chandler Hotel until it burned in 1885, and then took over the Grand Central. Mr. and Mrs. John Walters ran a hotel in Stoughton for a few years and in 1894, they bought the Grand Central Hotel.
In 1898, the Wisconsin State Journal reported that traveling men agreed the hotel to be one of the three best hotels in Dane County, outside of Madison—“originally like a large New England house, beds are the soft sleepy kind that cause one to dream of mother and apples dropping in the orchard while the night wind shakes the rafters.”
At some point, the name was changed to the Portland Hotel. After the hotel business declined, the front sections were owned and operated by various businesses and the back section was used as a home and for a few rental rooms.