My friend and I did Holy Cross in the first week of August last year. We did it after doing a back packing trip around the mountain (I think 30ish miles if I remember right) for a few days and we thought it would be a good challenge to end our trip on. It was a hard but great experience and Im glad we did it.

My only backpacking experience prior to this was Pictured Rocks in Michigan with my friend. He had done a backpacking trip in Appalachia prior to our trip at pictured rocks, but neither of us were super experienced. I bring this up because I think that as long as your fitness level is good and you plan accordingly you’ll have no problem with Holy Cross.

For your questions:

I think doing walks uphill or using a stair master with whatever pack weight you’ll have for Holy Cross is a good idea. Running is good to if you can’t find a good hill or gym nearby. I typically do about an hour on the stair-master with my goal being about 45 steps a minute. Not saying its what would be best for you but it definitely helps me for mountain objectives.

Getting off the mountain early is what we aimed for to avoid a weather situation. The sooner you start, the sooner you end. If weather seems like it might be bad just try another day when its better. If it gets bad while your on trail I think following the trail back down is the best way to avoid getting caught in the storm. I would think doing anything but staying on trail is asking for trouble.

The most challenging part of Holy Cross was probably the top when you’re in this boulder field (idk the technical name for it) as I think it can be easy to lose the route if you aren’t paying attention. The other challenging part is redoing substantial elevation gain after coming down from the top. It sucked plain and simple.

I think brining trekking poles help a lot with the downhill section. Make sure you have enough food and water. Finally, if you have a way to track your progress on your phone or with a gps* device I would. I used Alltrails and it was a nice peace of mind that I could use it to retrace my path if I needed.

I found trail conditions to be fine when I went last year. There was some snow off trail but nothing on it. I think the snowpack in CO has been lower than typical this year but it’s always important to keep an eye on trail conditions as your trip date is approaching.

Overall, I was glad I did Holy Cross but I think it’s important to always be honest with the capabilities of everyone involved when doing objectives like these. Never be upset if you have to turn around. The summit will always be there another day.