[1] The town began as a military outpost established near a small Shan village with two dozen households[2] on the Lashio-Mandalay trail between Nawnghkio and Mandalay.

In 1897, a permanent military post was established in the town and later, because of its climate, it became a hill station and the summer capital of British Burma.

The establishment in Burma (civil, commercial and military) would move to Maymyo during the hot season to escape from Rangoon's high heat and humidity.

[2][3] The military government of Burma renamed the town Pyin U Lwin, the word-for-word Burmese transcription of the Shan "City (ဝဵင်း, Weng⁴) of Paang²uu⁴ (ပၢင်ႇဢူး)".

Maymyo was an important educational centre during colonial times, with the GEHSs (Government English High Schools), such as St. Mary's, St. Michael's, St. Albert's, St. Joseph's Convent, and Colgate, are all based in the town.

Sweater knitting, flower and vegetable gardens, strawberry and pineapple orchards, coffee plantations and cow rearing are the main local businesses.

The most important flowers grown intensively are chrysanthemum, aster and gladiolus, which are exported to every corner of Myanmar throughout the year.