Over time Ashkirk and the surrounding area developed as a mainly agricultural community and there are various old drove roads that run though Ashkirk that were important routes for moving sheep and cattle. In later history Ashkirk became an important staging post to serve horse drawn stagecoaches with the Ashkirk Smiddy being a reminder of this. By the 1800s the present Church had been built, as well as the school, a small sub post office, and police station.
Around 1914 Ashkirk was used as a military training camp for Lothian & Borders mounted squadrons. The camp being set up during the summer in the area where the Woll golf course is now situated. This was a camp for mounted regiments, where both the horses and soldiers were trained in preparation for WW1.
By the time WW2 arrived Ashkirk was also notable as an important look out point for the Royal Observer Corps (ROC) as part of a strategic military defence manned by local volunteers. It was from the ROC look out point and subterranean bunker at Ashkirk that the plane carrying Rudolf Hess was identified as he attempted to make his escape. Using calculations based on his flying speed and altitude over Ashkirk led to directly intercepting Hess where he crash landed in Eaglesham. Notable residents of Ashkirk have included watercolour artist Euphen Alexander (nae Cochran of Ashkirk House), Olympic Event rider Sir Ian Stark OBE, Scottish international rugby player Doug Davies and poet Will H Ogilvie.
Although Ogilvie was born in Kelso he spent his latter years living in Ashkirk and drew inspiration from the hills and countryside surrounding Ashkirk.
William Ogilvie The Road to Roberton by Will H. Ogilvie - Scottish Poetry Library