Ashkirk is on the A7 about half way between Hawick and Selkirk. This route is all road and takes in a mixture of valleys and open upland which can be quite bleak in bad weather.
Take the road out of Ashkirk heading uphill for the Ettrick Valley. This is called the Woll. It's a fairly stiff haul for a while before emerging onto the Woll Rigg with open views in all directions. As the road starts to go downhill, the large estate and mansion you can see ahead of you over the valley is Bowhill. It belongs to the Duke of Buccleuch, as does much of the land hereabouts.
Turn L at the T junction and you'll reach the main road up the Ettrick Valley after a mile. Another mile and a half brings you to Ettrickbridge - the Cross Keys is the local pub and can be recommended.
It's a fair way along the Ettrick now to the Tushielaw Inn, an old pub but one which rarely seems open whenever I pass it. [update: this pub has now shut permanently] Turn L here to follow the Rankle Burn for a while before heading gently uphill. Craik Forest is over to your R and, almost at the top of the hill, opposite an entrance to the forest, you'll find a small cairn marking the spot of what once was Redfordgreen School. It opened in 1885, closed in 1955, and it would be difficult to find a bleaker place in winter to site a place of learning.
Go past Alemoor Loch and as you head just slightly upwards, the familiar outline of the Eildon Hills comes into view to the NE. Drop into Borthwickdale now. To the E is Ruberslaw and, further on, the Cheviot Hills.
Go L at the T junction then L again after 300m signed for Ashkirk and upwards to a junction at Blawearie. This is open country with extensive views. It's pretty well downhill most of the way now to cross the Ale Water from where it's a mile or so back to Ashkirk. On the route, you'll pass a cairn in memory of a Will Ogilvie who died in 1963. It's not clear just who he was or what the connection is - perhaps someone could let me know?
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