Highway 27 was marked in 1934. It replaced part of former State Highway 10 between Wheaton and Herman and part of State Highway 54 from Herman to Roseville Township; the remainder consisted of either concurrencies or new highways authorized in 1933. At this time, it was paved from Wheaton to Herman, along its overlap with U.S. 52 from Alexandria to Osakis, and from its junction with State Highway 28 to Pierz.[2][3]
It was paved from Long Prairie to its junction with Highway 28 in 1938,[4] and from U.S. 169 to then-State Highway 56 along the south side of Mille Lacs Lake in 1939.[5]
In the early 1940s, paving was done along short segments west of Wheaton, east of Osakis, west of Lastrup, and west of Moose Lake.[6]
After the end of World War II, the remainder of the highway west of Mille Lacs Lake was paved in stages, with these portions complete by 1955.[7]
In 1958, the roadway was realigned; instead of turning northeastward to travel through McGrath, it continued directly east to intersect Highway 65 at a four-way junction with then-State Highway 66.[8][9][10]
Highway 27 was relocated in 1961 along the routing of former State Highway 66 from State Highway 47 south of Isle to Highway 65 at Woodland. The 66 designation was simultaneously reused on another highway in Blue Earth County. Its former alignment from 47 to 65 was renumbered as part of State Highway 18.[11][12] Also in 1961, the highway was paved from the Aitkin-Carlton county line to the existing pavement near its crossing of the Kettle River.[13]
In 1970, the highway was extended through Moose Lake along former U.S. 61 and County Road 8 to an interchange with the newly built Interstate 35.[14]
The last remaining unpaved section, from Highway 65 to the Aitkin-Carlton county line, was paved in 1974.[15]
In 2012, Highway 27 was moved to overlap with I-94 from Alexandria to Osakis, with the old route turned over to Douglas County maintenance and renamed County Road 82. The highway was then routed along what had previously been State Highway 127 to connect with its existing alignment in Osakis.[16]
^1955 Official Road Map of Minnesota (Map). Cartography by The H.M. Gousha Co. Minnesota Department of Highways. January 1, 1955. § A-13 through J-12. Retrieved December 31, 2018.
^1958 Official Road Map, Minnesota (Map). Cartography by The H.M. Gousha Co. Minnesota Department of Highways. 1958. § K-11. Retrieved December 31, 2018.
^1959 Official Road Map, Minnesota (Map). Cartography by The H.M. Gousha Co. Minnesota Department of Highways. 1959. § K-11. Retrieved December 31, 2018.
^1961 Official Road Map, Minnesota (Map). Cartography by The H.M. Gousha Co. Minnesota Department of Highways. 1961. § K-12. Retrieved December 31, 2018.
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