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Follow the road leading there.
Or just beeline straigh to Ivarstead if you have it marked on map but unexplored.
From there you can't miss it where to go to High Hrothgar. Ask Klimek for the supplies delivery to earn some extra money for your climb too.
1. Whiterun - Go past honeymead brewery and cross the bridge towards whiteriver watch Pass the Something stone (I can't recall which one it is, has a necromancer). Hang a right and you should encounter a stormcloak camp. Facing the Camp (12 0clock) aim for 10-11 oclock and go up a path in the mountains. Go through that and you will come out in the reach (North of Iverstead). Follow the right side path past an abandoned well and across a stream. Go right (watch out for Troll) and follow the road to Iverstead. From there see Klimmik and a Bosmer talking. The bridge they are on leads to HH.
Path from Tundra Homestead :
https://i.imgur.com/FmPj8Pj.jpg
Path from Riften (fastest way imo) :
https://i.imgur.com/J89vyCo.jpg
No hard encounters along the way, just one bear at low level near honey strand cave but easily avoided. Much shorter and safer than the Riften route, or you can go north and east from Whiterun through Valtheim Towers, which then bends south but it's a longer route with more ambushes.