The name "Ashby" appears to be from the saxon "aesc" meaning Ash abd "byr", a habitation. "DeLa Zouch" was added in 1160 when Norman nobleman Alain de Parrhoet La Zouch inherited his position as Lord of the Manor by marriage. The family held the property until the 14th century when during the reign of Henry 1V it passed again by marriage to Sir Hugh Burell. It reverted to the crown in the reign of Edward 1V, who granted the manor to the powerful Sir William Hastings.
The Bull's Head in Market Street dates from the 14th century ad is said to be the oldest house in Ashby. After the surrender of the Castle in the Civil War, Cromwell's ordanance sergeant was billeted there while supervising the blowing up of the Castle Walls. The White Hart Public House was the last pub in Ashby to stage bear baiting. A bear pit can still be seen inside the pub. It is also reputed to have been a haunt for the notorious highwayman Dick Turpin
The medieval St Helen's Parish Church contains 8 bells dating from 1698 to 1849. St Helen's also boasts the only surviving "finger pillory" an instrument of punishment for absence from or misbehaviour in Church..
In the 19th century Ashby became a Spa Touwn when tourists visited Ivanhoe Baths. These were filled with water drawn from a Spa in Moira and moved by train. They were closed in 1884 and demolished in the 1960's. Now shopping is the attraction for visitors to the Town. A variety of locally owned and specialist shops trade alongside famous high street names. The Town also boasts an award winning Museum, nextdoor to the award winning Tourist Information Centre, and Ashby Castle is now owned by English Heritage.