Early evidence of Late Stone Age people crafting bone tools including bone awls and spear points has dated to about 77,000 years ago at:

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The evidence of Late Stone Age people crafting bone tools, including bone awls and spear points, dating back to about 77,000 years ago, was found at Blombos Cave. This site in South Africa has provided significant insights into the technological and artistic behaviors of early Homo sapiens.

Early Evidence of Late Stone Age People Crafting Bone Tools