Walkers usually tackle the Southern Upland Way from west to east in order to keep the prevailing wind to the rear. Its 212 miles runs from Portpatrick on the southwest coast of Scotland through relatively unknown and superbly unspoilt and varied countryside to the village of Cockburnspath on the eastern seaboard. Despite its outstanding beauty, the trail is exceptionally quiet and is a marvellous route for those seeking peace, solitude and wide open spaces.

Overall, the landscape is one of rolling hills rather than mountains, although there are plenty of stretches over 2000 feet in elevation and the remote nature of much of the route combined with the sometimes serious Scottish weather makes this a serious undertaking for those aiming to walk the entire length or the more isolated sections. The distances between accommodations can be quite long, over twenty miles in places, so many people choose to camp or arrange for collection by car at various points.
The trail begins with a gentle introductory section from Portpatrick along the beautiful coastline for a few miles before turning west across fields to Castle Kennedy. Here is where the true character of the trail becomes apparent with a long section over open moorland and through coniferous forests. Although a few roads are crossed en-route, this is essentially a wild and lonely place until you reach St. John's Town of Dalry. Keep an eye open on the way for the Beehive Bothy and White Laggan Bothy as places to shelter or overnight. The section through the Glen Trool forests by the side of the river and the loch is a scenic highlight of this part of the trail.