Herd Hill is a modest rise in the flat country near Annan, the sort of landmark that appears on a map without much fanfare. What matters is where it lies: on the Scottish shore of the Solway, in Annandale, a broad farming valley that runs up to the Southern Uplands. Annan sits on its river, once a port with tobacco and timber trade, and has a long history as a border town where English and Scottish armies fought over a place that changed hands many times.
The country is full of small, surprising stories. At Ruthwell, a few kilometres west, the church holds the Ruthwell Cross, an Anglo-Saxon stone cross from the eighth century covered in carvings and runic verse, one of the earliest pieces of English poetry. Thomas Carlyle was born at Ecclefechan, a short drive inland, and Robert Burns spent his last years in Dumfries, along the coast. The Solway estuary beyond is wide, silty and teeming with birds, and the tide runs in across the sands with remarkable speed.
The riding is calm, a succession of small B-roads between pastures and woods, over low rises like this one, with gates and cattle grids and the occasional farm lorry. Surfaces are variable, mud on the corners near farms is common, and in wet seasons roads flood in low spots. It is a good area for a lazy day at a measured pace, stopping where the view or the sun suggests. Winds from the west can be fierce, and sea fog sometimes rolls in.
Annan is close with fuel, a supermarket, bakeries and cafes. Dumfries, a bit further, has more, and the M74 corridor is near if you want a quicker route south to Carlisle. The best months are May and June, with long evenings and flowering gorse, or September, when the sky turns a clear pale blue.