re: Good pair of waterproof hiking shoes?

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Not really. For RMNP I’d say early May is 100% likelihood of being necessary. Late May is 75-90% likely.

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I'll agree with this, though more like 95% for late May. That's based on around 25 summers of hiking RMNP and living in Boulder for several years. It's not just the snow and runoff, if you are hiking in the afternoon it's pretty close to 50/50 that you will see rain, and some of it pretty heavy. We used to hit the trailhead just after dawn for that reason, and for better parking and less crowded trails.