Old U.S. 14 Between Winona and Stockton

March 1, 2009

“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.


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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.

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A retaining wall is visible from the modern highway.

Retaining Wall, Old U.S. 14

A closer view of the top of the retaining wall, taken from the old road grade.

The old 8-foot wide concrete slab sticks out through the fallen leaves.

The old 8-foot wide concrete slab sticks out through the fallen leaves.

A last view of the end of the old retaining wall, with the modern highway visible in the background.

A last view of the end of the old retaining wall, with the modern highway visible in the background.

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 old grade, stretching off into the woods.

The old grade, stretching off into the woods.

A close-up of the old concrete slab.

A close-up of the old concrete slab.

The view of modern U.S. 14 from the end of the old road, now a sheer cliff. The entrance to the scenic overlook is just visible in the lower left corner of the shot.

The view of modern U.S. 14 from the end of the old road, now a sheer cliff. The entrance to the scenic overlook is just visible in the lower left corner of the shot.

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.

Looking west, probably just before turning into the "Devil's Elbow"

An historic photo from sometime in the early 1920's. Looking west, probably just before turning into the "Devil's Elbow". The beginning of the stone retaining wall is visible just ahead. Also note the lone tree on the edge of the cliff.

Looking back to the east on the first curve into the "Devil's Elbow". Note the lone tree, which is possibly the same one as seen in the previous photo. You can also see how the road is half concrete and half gravel. Note how the caption says "Trail 7", referring to Constitutional Route 7, the original designation for U.S. 14 in Minnesota.

Looking back to the east on the first curve into the "Devil's Elbow". Note the lone tree, which is possibly the same one as seen in the previous photo. You can also see how the road is half concrete and half gravel. Note how the caption says "Trail 7", referring to Constitutional Route 7, the original designation for U.S. 14 in Minnesota.

The remains of the decorative retaining wall at the Devil's Elbow, also showing the old concrete pavement. A car passing on modern U.S. 14 is visible on the left.

The remains of the decorative retaining wall at the Devil's Elbow, also showing the old concrete pavement. A car passing on modern U.S. 14 is visible on the left. This segment is accessible directly from modern U.S. 14.

A postcard showing the "Devil's Elbow" as it appeared between 1921 and 1932. Note the wood guard rails, and the stone retaining wall.

A postcard showing the "Devil's Elbow" as it appeared between 1921 and 1932. Note the wood guard rails and the stone retaining wall.

The same retaining wall as seen on the historic photo today, now crumbling.

The same retaining wall as seen on the historic photo today, now crumbling.

Thanks to “Highway Explorer” for these great finds!

One Response to “Old U.S. 14 Between Winona and Stockton”

  1. My Dad almost died in a car accident on Stockton Hill when he was a twentysomething dumbass riding around with other twentysomething dumbasses. Fifty years after the fact we were driving out to visit my aunt in St. Charles and he flat out refused to take US 14 to get there or come back to our hotel in Winona. Really liked the pictures – not sure if I’m going to show them to Dad though.

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