Dating back to the 12th Century, the Old Town High Street was the centre for commercial activity before the development of the new town. During the 15th Century, London merchants built country houses in the area.

The town centre contains many listed buildings dating back to the 16th and 18th Centuries, which were the homes of wealthy merchants who lived in Stevenage. It is the main stagecoach station outside London and the main commercial centre back before the development of the new town.

The Old Town High Street, now a conservation area, gained its distinctive buildings over the next few centuries. One of the oldest remaining buildings is the original schoolroom of the Thomas Alleyne School, founded in 1558. The Old Town retains much of its old world charm and today it has a host of specialist shops as well as offices, restaurants, a hotel and public house in the area. Ample parking awaits those who visit this hidden treasure of Stevenage.