I will say for places to eat, go outside the park and go to Twin Butte for Mexican. If you decide to stay in Pincher it's on the way. Otherwise, Crandall is a nice place to stay. They just rebuil the Kilmory Lodge and it looks as though they did a great job there too.
Everyone has listed the hikes quite well and there are tips/tricks all over the internet for Crypt. September is a great time to go as it's no AS busy on the weekends. Weekdays are quiet for the most part.
Feel free to reach out if you have any further questions
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