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Opposite the Old Grammar School is the Mansion House, the former home of Dr John Taylor a livelong friend of Dr Samuel Johnson, who he regularly entertained, along with James Boswell, Johnsons biographer.In 1764, Dr Taylor engaged Robert Adam, who was working on Kedleston Hall, to re-design his house.
Originally, the town lay only to the north of the Henmore, with the tiny hamlet of Compton to the south.Ashbourne has managed over the centuries to preserve much of its architectural character.The medieval layout with a long straight main street and a large triangular market place has remained intact.The work was actually completed by the Derby architect, James Pickford, who turned the house into a miniature mansion.Amongst the many notable features is an octagonal drawing room beneath a copper dome.The Old Grammar School was founded in 1585 by the Royal Charter of Queen Elizabeth.
Four hundred years later, another Queen Elizabeth, the Second this time, visited Ashbourne to celebrate the 400th anniversary of the school.
Over the years the school had become too small to meet the needs of the 20th century and a new school was built on Green Road.
The old school continued in use for many years after that, but in 1997, the decision to sell the Grade I listed building was taken.
Looking back across the road at the Grey House, you will notice that it is built in a similar style to the Mansion House.
This is not an uncommon occurrence and there are other similar instances in the town.
This decides the sides for the famous Royal Shrovetide football games, which take place on Shrove Tuesday and Ash Wednesday every year.