[1] A long-distance trail in the Caucasus has been a lingering idea for trekkers and hikers for many years since they started hiking remote parts of the region.

At the same time, explorer Tom Allen began an attempt to hike the length of the Republic of Armenia, which was unsuccessful due to an absence of known routes and detailed maps.

Allen devised a 'Transcaucasian Trail' project to remedy these problems, and discovered Stephens' shared vision when attempting to register the same domain name, at which time the two decided to collaborate.

[2] In late 2015, Allen approached 4x4 manufacturer Land Rover and the Royal Geographical Society for funding to scout a potential route traversing the Lesser Caucasus through Armenia and southern Georgia, launching the 'Transcaucasian Expedition' in April 2016.

[3] In July of the same year, Stephens initiated the first trail construction and maintenance project in Svaneti, Georgia, employing international volunteers to carry out the work.