The line was constructed by the North Yorkshire and Cleveland Railway (NY&C) between Picton (on the Leeds Northern's 1852 route between Northallerton and Stockton) and Grosmont.

It was opened in 1857 from Picton to Stokesley, with intermediate stations at Trenholme Bar, Potto and Sexhow.

A 2 miles (3.2 km) branch to the ironstone mines at Ailesbury and Swainby left the line southwards after Potto station.

This was opened with the initial section of the line and forwarded two ironstone trains per day to the furnaces on Teesside.

Passenger services were withdrawn on 14 June 1954, with goods traffic ending west of Stokesley in 1958.