Caboose #99006 was built in 1886 by Barney & Smith of Chicago for the Wisconsin Central Railway, predecessor of the Soo Line. It is one of eight original wooden cabooses of its class delivered to the Wisconsin Central that year. Six more were built the following year by the Ohio Falls Car Company and another 24 were built in 1890 at the Wisconsin Central shops at North Fond du Lac. The original numbers assigned to these cabooses were in the hundreds, but when the Soo Line took over management of the Wisconsin Central Railway in 1909, all caboose numbers were changed to the 99000 series.
Caboose #99006 was one of the long ones—42 feet long, by 9 feet wide, by 15 feet high. The 16-ton caboose originally had 33 inch cast iron wheels, which were later exchanged for steel. The original color was box car red. This was later changed to cherry red for greater visibility and to warn the engineer of the train ahead. During restoration the caboose was repainted a shade of red that closely matches that of the original Wisconsin Central Railway.
The caboose was the living quarters and office for the train crew. The interior of the caboose features an original coal-burning stove, sink, toilet, sleeping berths and storage closets for railroad lanterns, tools, safety flags and personal items. It was hot in the summer, cold in the winter and noisy all year round. The cupola has 8 windows where crewmen could sit and view the train and track.
Caboose #99006 traveled the entire Wisconsin Central system and accompanied many freight cars and trains. In August of 1963 it was involved in a train wreck near Camp Lake in Kenosha County. The train was rolling along at about 75 miles per hour when, for unknown reasons, it went off the rails and on the ties.
A box car ahead of the caboose went end over end and hit the caboose, causing it to tip over on its left side. Ballast, or gravel, came scooping through the windows, and the crewsmen were badly shaken up and bruised by the bouncing. At the time #99006 went in for repairs resulting from the Camp Lake wreck, the siding was removed and replaced with plywood. This, of course, strengthened it considerably, but changed its appearance.
In 1974, after 88 years of service, #99006 was moved to the Oshkosh Public Museum where it was used to exhibit railroad memorabilia on the museum grounds for 16 years.
On November 13, 1900 the caboose was donated to the Manitowoc County Historical Society and moved to the Village by Eis Structure Movers (Two Rivers) where it joined the 1887 Soo Line steam locomotive, tender and flat car at the Collins Depot.
The caboose was laid on an additional 45 feet of track constructed by a volunteer crew, including retired Chicago & Northwestern railroad employees from Manitowoc. Restoration work was completed over a four year period. It included replacing exterior tongue-and-glove siding, badly deteriorated window trim, a side wall and a leaking roof, and the painting of the caboose.
It was opened to the public in the summer of 1994 and officially dedicated on May 21, 1995.