It's not impossible for the 'land bridge' to be open during summer months sufficient for game to travel over it, followed by hunters. Especially if, perhaps, their normal feeding grounds become barren from drought(?) or over-feeding; the animals just follow the growth of grass wherever it leads them. Whether they all reached the safety of the other-side before winter arrived is questionable, in which case they may have run quickly during autumn.
As to why no one does it nowadays could have something they didn't have then - political barriers.
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