The term "street" derives from its Old English sense (from Latin: via strata), which referred to any paved road and had no particular association with urban thoroughfares.

It crossed Hadrian's Wall through a large fortified gateway later called the "Portgate" which was still visible a few hundred years ago.

The A66 road preserves the route of the Roman-era Watling Street, branching off here to cross Stainmore to Penrith and Carlisle at the western end of Hadrian's Wall.

[11] Dere Street crossed the River Tees over a stone arch bridge near the present-day Piercebridge Roman Fort ruins.

[18] The route passes north into Redesdale and thence into the Cheviot Hills, where there are the remains of marching forts at Fourlaws, West Woodburn (Habitancum), Rochester (Bremenium), and at Chew Green.

The exact route of Dere Street through Lauderdale was investigated by the art historian Bendor Grosvenor and his wife Ishbel during the COVID-19 pandemic of 2020-21.

[20] Another well-preserved section rises through the Lammermuirs over Soutra Hill and on to Edinburgh, where Din Eidyn was a stronghold for the British Votadini tribe.

[22][23] Raymond Selkirk suggested that the ruins on the south side of the Tees at Cliffe are the remains of a dam;[24] the archaeological television programme Time Team investigated this in 2009.

King Malcolm IV established his Church and Hospital of the Holy Trinity halfway along this section to provide succour for the many pilgrims using it.

[28] After the destruction of the Border Abbeys during the "Rough Wooing" of Mary, Queen of Scots, by the Earl of Hertford's forces and during the Reformation of the Scottish Church, the route fell into disuse and disrepair.

Tough, vigorous men could walk from Darlington to York, and it was said that the quality of a horse could make the difference between a possible thirty and fifty miles per day.

Roads were described as so muddy and difficult between November and February that to finish the journey by daylight one could barely stop to eat; however a "royal highway" or alta via regia strata was passable in winter between York and Durham, and this could have been Dere Street.