The A258 is a local road from Dover to Sandwich via Deal. Effectively it consists of two separate routes, as traffic going directly between its two endpoints takes the A256 instead.
Our route begins at traffic lights on the A256, 200 m northwest of that road's Townwall Street junction with the A20, and immediately begins climbing the steep tree-lined hill past Dover Castle using that old trick – sharp bends – to reach the summit. The site of this 12th-century castle is also home to a vast network of Second World War tunnels, a Saxon church, and a Roman lighthouse built in 46 AD.
After some open fields, we reach the roundabout with the A2 (which has taken a less winding and faster route from Dover) and continue straight ahead. This next section of road now has a 50 limit, which is strange as it seems devoid of habitation!
The pleasant village of St Margaret's at Cliffe (which has two lighthouses) is nearby, but we continue to Ringwould. There is a tree-lined dip before this village which merges seamlessly into Walmer and (after we meet the B2056 and come within sight of the sea) Deal.
There is a gentle descent to the seafront of this town which, in terms of population, is surprisingly as large as Dover. We pass Henry the Eighth's typically round castle and enter a brief one way system, TOTSOing right and then left to run along the seafront (note the lengthy pier).
Pedestrian crossing on High Street, Deal
Having bypassed Deal's High Street, we TOTSO left again at a roundabout and cross the railway as we leave the town. We meet the B2056 again in Upper Deal before reaching open country. There are a couple of hamlets to punctuate the flat run to Sandwich. A more interesting route from Deal to Sandwich is a toll road via Sandwich Bay golf course – the British Open has been played here.
On the southern edge of Sandwich we reach a roundabout and turn left which leads us out to the A256 bypass where the A258 ends. However, it is well worth a detour to the right for a look around this ancient and compact little town with its narrow bridge over the River Stour.
The A258 originally ended on the then-A256 Dover Road just south of Sandwich town centre, and appears to have survived the construction of the Sandwich Bypass in 1981 by some years.