Ashby is best known for its Castle, but did you know that the property began as a manor house in the 12th century and reached castle status in the 15th century. Built in the 15th century by the first Lord Hastings. The castle is an impressive ruin of a late medieval castle, dominated by its magnificent tower. It was here that Mary Queen of Scots was held prisoner for a time by Lord Hastings's grandson first Earl of Huntingdon.

Many of the buildings in Market Street, the town's main thoroughfare, are timber framed. Most of this structure is hidden by later brick facades.

The Ivanhoe Baths was an 1822 Neo-Grecian building with a Doric façade, it became derelict by 1960, and was demolished in 1962. The baths stood near to 'The Royal Hotel, originally called the Hastings Hotel, was built in 1826 to accommodate visitors to the growing spa. The hotel closed in February 2018.