When reading various types of Ancient Greek writings, to the best of my recollection, I don't remember any lengthy or even a minor discussion which referred to any group of humans or an individual person climbing Mount Olympus.
For the Ancient Greeks, Mount Olympus was their most sacred place....it was the place where 11 of the 12 main Deities resided-(not including, Hades). Perhaps the Ancient Greeks believed that this most sacred of sites, should remain as such and not be challenged by human adventurism....(and folly).
It should be noted that nearly 40 years ago, a team of Greek Archeologists literally unearthed the Ancient Greek city of Dion, at the foot of Mount Olympus. The archeological site of Dion, was a type of mini Pompeii, whose panorama....was the sacred mountain. Dion was apparently founded around the 600's BC/BCE, though was destroyed by an earthquake, followed by invading Goths from the Germanic hinterland 1600 years ago.
King Philip of Macedon, his son, Alexander The Great and even Augustus Caesar, visited the city of Dion. Interestingly, we have no archeological or historical evidence that any of these famous Ancient Leaders ever led a military expedition up the Mountain, nor do we have any archeological or historical evidence that the residents of Dion ever climbed Mount Olympus routinely-(or even infrequently).
Perhaps a further archeological inquiry may provide us with some proof that Ancient Greeks living in Dion-(or elsewhere in Greece proper), climbed Mount Olympus. However, until then, we have no evidence that the Ancient Greeks ever climbed Mount Olympus.