Hugh Waydelin Crickmay was born in Oatlands, Chertsey, Surrey, England on 8 November 1908 and was the son of the architect George Lay Crickmay (1855-1921) who, in 1881, with his father George Rackstrow Crickmay (1831-1907), founded the architectural practice Crickmay & Son [from c.1894 Crickmay & Sons] which had offices in London and Weymouth Dorset.
Hugh Waydelin Crickmay studied at the Bartlett School of Architecture, University College, London and commenced practice as an architect in Slough, Berkshire. In 1937, with his cousin, Colin Rosser Crickmay (1904-1999), he took over the family practice in Weymouth which was subsequently known as C.R. & H.W Crickmay & Sons. The London office of Crickmay & Sons in Victoria Street was bombed in World War Two but C.R. and H.W Crickmay never worked there.
Hugh Waydelin Crickmay was elected an Associate of the Royal Institute of British Architects (ARIBA) in 1931. He retired from practice in 1977 and died in Weymouth, Dorset on 27 January 1978 at which point C.R. & H.L Crickmay & Sons may have ceased.