Bridge No. L-1409, with its coursed-ashlar masonry and 45-foot span, is historically significance as a bridge that combines a concern for workmanship and a massiveness of scale that makes it the state's most impressive, country, stone-arch bridge.
On September 21, 1894, residents of Hillsdale Township petitioned the Winona County Board of Commissioners to build a bridge in Section 23 across the South Branch of the Rollingstone River at the crossing of the Hart Hill Road. According to the Proceedings of the Winona Board of County Commissioners, the petition was "laid over for future discussion." Although there is no record of subsequent debate, the petition apparently was approved on October 10, 1895. The board considered eight bids "for construction of an arch bridge of stone" at the requested site "as per plans and specifications in the Office of the County Auditor." The board's minutes also note that the plans had been prepared by Fred H. Pickles, county surveyor in 1895 and 1896. The successful low bidder at $1,340 was Charles Butler, a local stonemason. In December, 1895, "engineer Pickles" reported to the board that Butler had faithfully fulfilled his contract on the stone-arch bridge, except for the "pointing," which presumably was completed the following spring. No other surviving architectural or engineering works by either Pickles or Butler have been identified.
Bridge No. L-1409 belongs to the category of "country" stone-arch bridges. Concentrated in the southeastern section of the state, these structures were primarily built by local governments during the late 19th and early 20th centuries as part of the "Good Roads Movement," a coalition of farmers, bicyclists, motorists, engineers and politicians who were intent on improving the quality, comfort and safety of rural highways and bridges. Typically, country stone-arch bridges are modest rubble-masonry, back-roads structures, rarely exceeding 15 feet in span. In contrast, Bridge No. L-1409 displays a 45-foot span and well-crafted ashlar masonry. Although its origin and location clearly establish its "country" lineage, the bridge rivals in scale and sophistication the stone-arch highway bridges known to have been built in the state's urban centers.