Settlement began here in 1756 when the track on this straighter route from Poole to Ringwood was made into a road. Travellers could then bypass Kinson when a new inn, The Shoulder of Mutton, was built to cater for them.
The area was initially called Beare Bottom. Beare coming from the Old English word 'bearu' meaing woodland and Bottom due to being located near the bottom of the Stour Valley. On a map from 1778 the area was simply called 'Beare'. The strips of woodland or bearu still survive and give us the modern name Bearwood which neighbours Bear Cross. At the beginning of the Victorian Era the final ‘e’ had been dropped and the name for the wider area at this time was Cudnell. By the end of the 19th century, Bear had almost died out.
An alternative source of the name is reputed to have been derived from a local bear pit where bears were taught to dance and pitted against dogs in fights over which wagers were taken. This happened on the heathland which historically covered the area until the expansion of Bournemouth and Poole overtook it during the Twentieth century. This activity is reflected locally in the badge showing a bear in chains which appears on both the sign of the Bear Cross pub at the roundabout, and that of the local Oakmead College of Technology.
The longest road in Bournemouth, Wimborne Road, ends at the Bear Cross roundabout. House numbers reach 1714 on the even side and 1823 on the odd. It used to extend all the way to Canford Magna, along what is now Magna Road.