Size Obsession

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I use the Sea To Summit dry bags and most of my stuff compresses reasonably well when you roll down the collar (say a 1:3 ratio or something along those lines). I did buy a compression sack for certain uses but I found the straps annoying on it when opening/closing so I stopped using. And most of the stuff like fire starters and the like are not compressible anyway so the sacks are more about organization than space.
Tight stuffing of small incompressible objects into stuff sacks actually wastes more space than loose stuffing once you put several such stuff sacks in your pack.

As far as water I do usually stop. I used to use (well use off and on - still undecided) a small Ribz type set up (because of course I have no space! :) ) that I'd put essentials in to avoid stopping (compass, camera, an 18oz Hydroflask, toilet paper, clotting gauze and other stuff that is super easy to have at your fingertips or super important to get as fast as possible). I find I need to force myself to stop at periodic intervals to give my legs a breather and avoid overheating (say every 2 hours or so) so that's when I'll normally chug some water and eat something. Because I do all of my hikes as day hikes with lengthy amounts of driving I've found these periodic stops are better over all for avoiding cramps on the drive home and fatigue in the following few days (I am not in anywhere near the kind of shape you are). In the past I would just crank it out of the woods to get finished up. Now I make it a point to break it into intervals for rest/water/food even if I don't feel tired, thirsty or hungry. For whatever reason I find I need far less water in winter despite what most people say about needing more. As I've experimented I've found I get much better performance hydrating and eating on my drive up to hike which probably contributes to why I seem to need less during the hike.
Thirst is suppressed by the cold--you should judge your water needs in winter by urine volume and color.

I have adopted a time based protocol in winter--I stop once an hour (by my watch) to eat and drink. (When hiking one can put food and water in one's pocket and eat and drink without stopping, however this is difficult to do when one has ski poles in one's hands... The time-based protocol is my way around this problem.)

In summer, I carry a 24oz water bottle in my pocket so I can drink without stopping. (I don't like bladders and they can be unreliable in winter.) I carry several of the bottles in my pack so I can simply switch bottles rather than waste time refilling bottles. In winter, I carry insulated water bottles in my pack.


Back to the original question:
I have packs in several capacities and choose one that can comfortably carry whatever gear I think is appropriate. I avoid tying gear on the outside.

Doug
 
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Tight stuffing of small incompressible objects into stuff sacks actually wastes more space than loose stuffing once you put several such stuff sacks in your pack.

It does, however, have the positive effect of reducing the chances you will drop said small, incompressible objects in the surround snow, possibly losing them until spring, or dropping other items in the snow while searching around inside your pack for the same. I.e., organization, but dropping the whole stuff sack probably keeps things dry and not lost or buried. I like to have one dry bag and/or plastic bag to stash wet or damp items like spent glove liners or the shirt I wore on the ascent. I also use the compression pocket on the back for these items if I have lined my pack with a kitchen garbage bag to keep the snow out.

I tend to fill those odd spaces with my wind pants, or heavy mittens, Thermos, or food.

Tim
 
It does, however, have the positive effect of reducing the chances you will drop said small, incompressible objects in the surround snow, possibly losing them until spring, or dropping other items in the snow while searching around inside your pack for the same. I.e., organization, but dropping the whole stuff sack probably keeps things dry and not lost or buried.
You may have misread my post: I was comparing stuffing small incompressible objects tightly in several stuff sacks vs putting small incompressible objects in loose stuff sacks. Both procedures protect against dropping in the snow and provide the same organization. The difference is in the total packaging volume. (The loose stuff sacks require less total volume.)

Actually, the protection against dropping in the snow is better with the loose stuff sack because you can rummage around in the stuff sack to find an object without removing anything. In a tight stuff sack, you may have to remove some objects to find the desired object.

Doug
 
Thirst is suppressed by the cold--you should judge your water needs in winter by urine volume and color.

Doug

I usually stop to urinate 2-3 times on a typical winter hike and unless I really avoided water the color is usually reasonably light. I think the pre-hike hydration and frequent stops to catch my breath probably keep me from really burning off a lot of water. In summer it is not unusual for me to kill 3 32oz Nalgenes and filter a 4th if possible yet I don't really urinate and usually drink tons of liquids on the ride home. In winter I only carry 2 32oz Nalgenes and depending on length of hike I don't even drink both. I find water gives me a brief nauseous feeling in winter too for some reason. It is far worse when the water is very cold but it seem to do it no matter what.
 
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