Beat all of the gyms in kanto and then go to the professor he will probably give you a pass then go to mount silver.even if he does not give you any thing still go to mount silver any ways
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Well, to go to Diglett's Cave, you have to Vermillion City in the Kanto Region.
When you get to violet city go to the pokemon center go left then down then you will come up on a place called route 32 and at the end you will find a pokemon center and a cave and thats union cave.
Technically Ash is not in Pokemon Crystal, instead there is trainer Red but we all know it is Ash. Trainer Red (Ash) is located in Mount silver. After you get every badge in the game, go to prof. Oak and he will unlock mount silver for you. you must use flash to see inside the cave and look around for Trainer Red.
I don't know if you can get it in crystal, but i know you can get it in Gold and Silver versions. So you go to Union Cave. then you take a secret path (involves surf) and you go to this small patch of grass. In there you can find Smeargle (I think that's how you spell it) and Natu. Again i'm not sure if you can find them in crystal.
go right from mahogany town and then go in to the cave and it will be icy it is (a bit) rare (i mean only a bit rare)