Henry or Harry Maidment was born in Shoreditch on 29 April, 1868 the son of William and Annie Maidment. His parents were from Frome, Somerset and his father was a cabinet maker. The family lived at Prebend Street, Islington. His elder sister Ellen, who was 17 years his senior, married the artist Octavius Thomas Clark. Clark is widely believed to have taught Maidment, as their style and subject matter are similar. He married Alice Fisher Piggott in 1894 and they lived at 81, Elizabeth Avenue in Islington.

He was actually christened Harry, a name which is listed on all public records including birth, death and censuses. However, at some point the name of Henry was attributed to him, possibly in error as he usually signed H Maidment or with a monogram. He also worked under the pseudonyms of Robert or Robin Fenson and Arthur Wynne. In 1897, under the latter name, he exhibited at the Royal Society of British Artists.

Maidment travelled widely across the south of England, painting views of Surrey, Kent, Sussex and Essex. He also painted in Wales and Warwickshire. His skilled execution and gentle rural subject matter have made his works as popular today as they were in his lifetime. Maidment died in Nottingham in 1942.