Duggleby is a hamlet in the civil parish of Kirby Grindalythe, in North Yorkshire, England. It was historically part of the East Riding of Yorkshire until 1974. It was part of the Ryedale district from 1974 to 2023. It is 20 mi north-east of York and 16 mi south-west of Scarborough. The village lies in the Great Wold Valley and the course of the winterbourne stream the Gypsey Race passes through it. To the south-east of the hamlet is Duggleby Howe, one of the largest round barrows in Britain. Duggleby was formerly a township in the parish of Kirby-Grindalyth, in 1866 Duggleby became a separate civil parish, on 1 April 1935 the parish was abolished and merged with Kirby Grindalythe. In 1931 the parish had a population of 155.