STOCKTON, Minn. — Crews are 2-1/2 months into the $7.3 million upgrade of U.S. Highway 14 over Stockton Hill and on schedule. The target remains late October to reopen the route, the state highway department said. The engineering challenge has been decades of erosion from runoff down the nearly vertical bluffs along the entire seven-mile climb on both sides. The contractor, Mathiowetz Construction of Sleepy Eye, is tackling the project in 20 units. These include massive retaining walls for a wide right-of-way, improved drainage to curb erosion, and better guardrails. Yes, it’s a long way down. Alas, just like the days of yore there’s no solution for the near-hairpin curves near the summit on both sides. Meanwhile, until the project is completed, motorists and grain trucks are taking a longer route along Garvin brook between Stockton and the upriver Winona suburbs of Minnesota City and Goodview. But wait, there’s more. The road surface over Stockton Hill will be temporary, just for winter. Repaving won’t come until 2026. So too will be more detours.
Earlier: Stockton Hill upgrade begins Monday

Holding back the bluffs. New retaining walls have concrete and metal anchors deep into the bluffs to curb new erosion. One goal is a wider right-of-way. The route now is three lanes – one downhill and two hill for passing. Image: Minnesota Transportation Department
Topography profile
The highway over Stockton Hill connects Gilmore Creek in Winona with Garvin Brook in Stockton. Early settlers, mostly on foot but some on horses, used the pass as a shortcut. The path evolved into a wagon trail, then an unpaved Model T route. Near the summit on both sides were wide spots where early motorists stopped to cool their engines and refill their radiators with water from spring-fed creeks flowing off the bluffs. By the 1950s, the era of “See the USA in Your Chevrolet,” the road had been paved and was promoted for tourism as the Black and Yellow Trail from Chicago to the Black Hills of South Dakota and Yellowstone Park. While Interstate 90 has supplanted the route for transcontinental commerce, U.S. 14 remains heavily bused for local connectivity. This includes Rochester-Winona commuting over Stockton Hill.
Databank
Elevation at summit: 1,284 feet above sea level.
Rise from Winona: 758 feet.
Rise from Stockton: 743 feet.
Comment: Why not tunnel
Norwegians love to tunnel. The Swiss do it instinctively. But not the Minnesota Department of Transportation. Instead of pouring million of dollars again and again into fixes on the seven miles of U.S. 14 over Stockton Hill, why not a one-mile tunnel? No more icy and sometimes fatal wipe-outs on the steep, narrow and 45 mph twists up above. Millions of dollars could be saved in fuel costs for the current 700-foot elevation climbs on both ends. The environment would be appreciative. Commute time would shrink. Think about it: 70 mph all the way between Winona and Stockton and illuminated day and night. Too expensive? The Norwegians do it. The Swiss do it. Hawaiians have done it in Honolulu with the Tetsuo Harano tunnels. Seattle did it in 1938 with the Mount Baker tunnel to the Lake Washington floating bridge. /jv