Decided to do this hike instead of Headwall/Fortress/Chester:
The forecast had some lightning in it and I didn't really feel like being exposed on Fortress for that show! Turned out to be a good call, on our way out the top of Fortress was enveloped in clouds/rain. That, and my wife doesn't have proper hiking boots and probably wouldn't have done well with the length/difficulty of the loose rock. We will have to work up to that one!
Turned out to be a decent hike for us, anyway. This was kind of a "redemption" hike for me as in grade 7 we did a camping trip followed by a hike. It rained/snowed all night, and we were all cold wet and miserable. Our gym teacher didn't care, and dragged us up this. We made it about half way before the knee deep snow and 1m visibility blizzard finally made him realize dragging 40 kids up this might actuality be a really bad idea. Since then, even the mention of "Pickle Jar Lake" hike gave me a giant nope! So good to finally make it up!