1920s SR 27 was established at least as early as 1919 from Hawkinsville to a point northwest of Brunswick. It was also designated south-southwest and curved to the southeast to end at
SR 40 northwest of
St. Marys. At this time,
SR 28 was established from SR 39 in Georgetown to SR 7 in Vienna. By the end of 1921, SR 50 was established on its current path in Georgetown, becoming SR 27's new western terminus, since SR 39 was shifted southeast and out of the city. The eastern terminus of SR 27 was then indicated to be at SR 25 in Brunswick. SR 27 had a segment northwest of Brunswick, which meant that it intersected itself. It was then proposed south-southwest to SR 40 in
Kingsland. By the end of 1926, US 341 was designated on SR 27 from Hawkinsville to Brunswick. The separate segment from north-northwest of Brunswick to Kingsland was redesignated as US 17/SR 25. Nearly the entire Sumter County portion of the Preston–Americus segment of SR 28, as well as the portion of US 341/SR 27 east of US 17/SR 25, had a "completed hard surface". A portion of US 341/SR 27 straddling the Wayne–Glynn county line had a "completed semi hard surface". Nearly the entire Dooly County portion of the Americus–Vienna segment of SR 28 had a "sand clay or top soil" surface. Four segments of US 341/SR 27 also had this type of surface: the entire Telfair County portion, nearly the entire Appling County portion of the Hazlehurst–Baxley segment, from Baxley to just east of the Appling–Wayne county line, and the northern part of the Jesup–Brunswick segment. A portion of SR 28 east-southeast of Preston, as well as nearly the entire Wayne County portion of the Baxley–Jesup and the central portion of Glynn County segments of US 341/SR 27, was under construction. By the end of 1929, US 341/SR 27 had a completed hard surface west-northwest of Jesup. East of Lumpkin and in the Preston area, SR 28 had a sand clay or top soil surface. Southeast of Baxley, US 341/SR 27 also had this type of surface. Three segments of US 341/SR 27 were under construction: from Hawkinsville to Eastman, from McRae to Lumber City, and the entire Appling County portion of the Hazlehurst–Baxley segment. Two segments of US 341/SR 27 had completed
grading: nearly the entire Lumber City–Hazlehurst segment and nearly the entire Appling County portion of the Baxley–Jesup segment.
1930s By the middle of 1930, SR 28 was extended northeast to Hawkinsville. The entire Glynn County portion of US 341/SR 27 had a completed hard surface. A portion of SR 28 east-southeast of Preston, as well as the McRae–Lumber City segment and Wayne County portion of the Baxley–Jesup segment of US 341/SR 27, had a sand clay or top soil surface. A portion of SR 28 west-northwest of Preston was under construction. By the end of the year, a portion of US 341/SR 27 east-southeast of Baxley had a sand clay or top soil surface. SR 28's segment between Richland and Preston, as well as the Dooly County portion of the Eastman–McRae segment of US 341/SR 27, and a portion of those highways northwest of the Wayne–Glynn county line, was under construction. By the end of 1931, US 280 was designated on SR 28 between Richland and Americus. Three segments of US 341/SR 27 had a completed hard surface: from Hawkinsville to Eastman, from northwest of McRae to Hazlehurst, and from east-southeast of Hazlehurst to Baxley. Two segments of those highways were under construction: from Eastman to northwest of McRae and a portion east-southeast of Hazlehurst. In April 1932, the Hazlehurst–Baxley segment of US 341/SR 27 had a completed hard surface. By the beginning of August, their segment between Eastman to McRae was also completed. In September, the Vienna–Hawkinsville segment of SR 28 had a sand clay or top soil surface. Late in 1934, the northern half of the Appling County portion of the Baxley–Jesup segment of US 341/SR 27, as well as a small portion east of the Appling–Wayne county line, had a completed hard surface. In the second quarter of 1935, two segments of US 341/SR 27 had a completed hard surface: from Baxley to just east of the Appling–Wayne county line and nearly the entire Wayne County portion of the Baxley–Jesup segment. A small portion east-southeast of the Appling–Wayne county line had completed grading, but was not surfaced. By the beginning of October, the entire Wayne County portion of the Baxley–Jesup segment had a completed hard surface. A portion just west of the Appling–Wayne county line was under construction. By the end of the year, from Baxley to a point southeast of Jesup, US 341/SR 27 had a completed hard surface. Near the end of the year, from Richland to just west of the Webster–Sumter county line, SR 28 was under construction. The year ended with two additional changes to SR 28. From northwest of Preston to east-southeast of it, the highway had a completed hard surface. From Richland to northwest of Preston, it had a sand clay or top soil surface. In the first quarter of 1937, a portion of SR 28 in the southwestern part of Hawkinsville had a completed hard surface. It was under construction from just east of the Dooly–Pulaski county line to southwest of Hawkinsville. In the third quarter of the year, the entire Jesup–Brunswick segment had a completed hard surface. At the end of the year, the entire length of SR 28 was redesignated as a western extension of SR 27. From the Dooly–Pulaski county line to southwest of Hawkinsville, the highway had completed grading, but was not surfaced. The western half of the Lumpkin–Richland segment was under construction. In 1938, from east-southeast of Preston to east of the Webster–Sumter county line, SR 27 was under construction. By the middle of 1939, US 25 was extended southward, onto the Jesup–Brunswick segment of US 341/SR 27. The western part of the Lumpkin–Richland segment had a completed hard surface, while the central part of it had completed grading, but was not surfaced. A portion east of Americus was under construction. In the third quarter of the year, this segment had completed grading, but was not surfaced. At the end of the year, a portion just west of the Dooly–Pulaski county line was under construction.
1940s to 1990s In the first quarter of 1940, the entire Preston–Americus segment had a completed hard surface. In the third quarter of the year, the western half of the Quitman County portion of the Georgetown–Lumpkin segment was under construction. During the second half of the next year, a portion east-northeast of Vienna had a completed hard surface. The western half of the Quitman County portion of the Georgetown–Lumpkin segment had completed grading, but was not surfaced. The western part of the Webster County portion of the Richland–Preston segment was under construction. In 1942, from just east-northeast of Richland to Preston, the highway had a completed hard surface. Between the beginning of 1945 and November 1946, a portion from just west of Richland to Preston was hard surfaced. By February 1948, four segments were hard surfaced: from Georgetown to a point west-southwest of Lumpkin, the Lumpkin–Richland segment, a portion east-southeast of Americus, and the entire Pulaski County segment. Also, the eastern part of the Sumter County portion of the Americus–Vienna segment had a sand clay or top soil surface. By April 1949, the entire Georgetown–Lumpkin segment was hard surfaced. Between August 1950 and January 1952, the eastern half of the Dooly County portion of the Americus–Vienna segment was hard surfaced. In 1953, the entire Dooly County portion (except the extreme western part) was hard surfaced. Between June 1955 and July 1957, the entire highway from Georgetown to Brunswick was paved. In 1972, SR 39 was extended northward on the westernmost portion of SR 27, as it travels today. Between the beginning of 1981 and the beginning of 1987,
SR 782 was proposed between US 25/US 341/SR 27 and
SR 27 Alt. In 1989, a southwestern
bypass of Eastman, designated as
SR 841, was proposed from US 341/SR 27 west of the city to US 23/US 341/SR 27 southeast of it. In 1993, US 341/SR 27 through Eastman was shifted southward out of the main part of the city onto the path of SR 841. Their former path was redesignated as
US 341 Bus./
SR 27 Bus. Between the beginning of 1987 and the beginning of 1997, US 23/US 341/SR 27 through Jesup was shifted northeast onto the path of SR 27 Alt. and SR 782 ==Major intersections==