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This is the main commercial thoroughfare of the town. Old half-timbered buildings stand side by side with houses of modern design, small businesses jostle with national institutions to make up a lively balance of retailing and financial transactions. The Bull's Head is said to be one of the oldest houses in Ashby, and dates from the 14th century. After the surrender of the castle in the Civil War, Parliament's ordnance serjeant, Bainbrigg, was billeted there while supervising the slighting of the castle buildings. Other public houses have interesting histories too: The Shoulder of Mutton is reputed to have been the place where early 'moving pictures' were shown against its outside wall;

The White Hart was the last place in Ashby to stage bear-baiting and had the dubious honour of being 'the bawdiest public house in the Midlands' in the 19th century. The Queen's Head was one of the great posting-inns of the town in the late 18th and early 19th centuries.

The Town Hall, built in 1856 on the site of the Bear Inn, ceased to be used by the Council some time ago, but it still holds the town's indoor market. The town's War Memorial recently refurbished, standing at the junction of Brook Street and Market Street, was unveiled by Sir Joseph Hood, Bart., and Lady Hood on 8 June 1922. It now also bears the names of the dead of the 1939-1945 war and is the focus of the annual Remembrance Sunday parade and service.

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