“Highway Explorer” has found and photographed three long lost sections of U.S. 14 between the towns of Winona and Stockton in southeastern Minnesota, complete with original pavement and retaining walls! These sections were once part of one of Minnesota’s first concrete highways, constructed by Winona County between 1914 and 1915. This early highway was actually only half paved: one lane was made up of a narrow 8 foot wide strip of concrete pavement, while the other was given a standard gravel surface. The old road hugged the bluff line closely and made many dangerous sharp turns above steep wooded cliffs and hills.
The road between Winona and Stockton became part the trunk highway system in 1921 as part of Constitutional Route 7. It later became part of U.S. 14 in 1926 (the two routes were marked together until 1934). Decorative stone retaining walls were constructed in two locations on the hill in 1921 to improve safety, along with some standard wood guard rails (sections of both stone walls survive today, read on for pictures/ details). The original paved road remained in use until 1932, when the Department of Highways constructed a new grade along the alignment still in use today, which was designed to lessen the severity of the sharpest turns and reduce the steepness of the grade.
The first section we have photos for is just east of the scenic overlook near the top of the Stockton Hill, east of a deep gully on the north side of the highway. (Click here to see a birds eye view of the location, the stone wall is just visible.) The old road is only accessible by foot; blasting of the cliff face just to the east has disconnected the old road from the new highway.
The next section is just above, and to the west of the scenic overlook at the top of Stockton Hill. It can be accessed on foot via an entrance on Quarry Hill Road (Rural Route 3), just northeast of the monastery. This surviving section is much longer, extending east into the woods until it ends at a sheer cliff, blasted for construction of the modern highway. (Click here for a birds eye view).
The third segment was once known as the “Devil’s Elbow”, which was an incredibly sharp turn on the western slope of the Stockton Hill. Click here to see it in bird’s eye view). This was the second location where stone retaining walls were constructed in 1921. This curve was also a favorite of photographers of the time.
Thanks to “Highway Explorer” for these great finds!