re: Good pair of waterproof hiking shoes?

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Okay so our trip is May 21-28th so is that late enough where waterproof shoes are not necessary as often as early spring?

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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. Hell the vast majority of my may travel in that park has been in ski boots. As a point of reference, the road the bisects the park won’t open until the 26th.