Milwaukee–Watertown Plank Road

[1] According to former Watertown Daily Times editor Tom Schultz, portions of the plank road extended past Watertown to the Town of Portland:My Hubbleton friend said he could remember probably back in the 1950s when highway 19 was being reconstruced in the Hubbleton area, that under the pavement, construction crews found remnants of the old Plank Road.

An early manuscript by James A. Sheridan said the “foundation for a prosperous village (Portland) was laid around 1850 which was on the line of the Milwaukee and Watertown Plank Road.”[2] In early frontier Wisconsin there were no roads or railroads.

In good conditions they bumped over barely-covered stumps; when it was wet they were churned into strings of mud-holes.

The terms of the company's charter allowed them to charge a toll, and they made as much as $1300 per week on an initial construction investment of $119,000.

[5] Truman H. Judd, later a Milwaukee industrialist and state legislator, was the principal contractor, and served as the road's superintendent for four years after he completed construction.