Ainslie was born in Jedburgh, the youngest son of John Ainslie, a druggist, Writer to the Signet and burgess of the burgh. He was educated at Jedburgh Grammar School. He began his career as an apprentice to the "Geographer to King George III", engraver and publisher Thomas Jefferys and worked as a surveyor and engraver for the English County series of maps. After Jefferys' death he returned to Scotland where he surveyed Scottish counties, engraving and publishing the maps. His primary focus was on the coasts and islands of Scotland. The quality of his maps challenged others to improve their mapping style making maps more clear and easy to read.
From 1787 to 1789 Ainslie worked on a new nine sheet map of Scotland publishing it in 1789. The map was a landmark in the improvement of the outline of Scotland and for the first time showed the Great Glen as a straight line and Skye, Mull, and Islay shown with more accuracy than had previously been seen.
On the side John was a book seller which helped him in writing and publishing works of his own.
- The county of Fife published in 1775
- Scotland, drawn from a series of angles and astronomical observations..., in 9 sheets, published in 1789
- A plan of Jedburgh published in 1780
- City of Edinburgh published in 1780
- Ainslie's Map of the Southern Part of Scotland published in 1821
- "John Ainslie". The Gazetteer for Scotland. The Gazetteer for Scotland. Retrieved 17 May 2011.
- Adams, Ian. "Ainslie, John (1745–1828), cartographer and land surveyor". Oxford Dictionary of National Biography. Oxford University Press. Retrieved 5 February 2014.
- "A Selection Of Famous Jedburgh People". Jedburgh Official Website. Jedburgh Official Website. Archived from the original on 22 July 2011. Retrieved 17 May 2011.
- "Famous Sons and Daughters". Jedburgh Grammar School. Jedburgh Grammar School. Archived from the original on 27 June 2011. Retrieved 17 May 2011.
- Ainslie, John (1789). "Scotland, drawn from a series of angles and astronomical observations..." Edinburgh: J. & J. Ainslie & W Faden. Retrieved 5 February 2014..
- Ainslie, John (1812). "Comprehensive treatise on land surveying, comprising the theory and practice in all its branches; in which the use of the various instruments employed in surveying, levelling, &c. is clearly elucidated by practical examples ..." Edinburgh: Printed for S. Doig & A. Stirling. Retrieved 5 February 2014.
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