Brian, you are a sicko for doing this 3 times. Before starting, I thought fall would be the best time for this route -- not so hot and the bushwhacking wouldn't be as much of a problem. But as I approached, I realized that there would probably be ice and snow and running water to make it slippery. Yep! And the bushwhacking was still horrible. My forearms got slashed up (wear long sleeves as well as long pants if you're crazy enough to do this). Really, just go up through the lower tunnel, maybe the upper one, and work your way over to the Royal Arch and call it good. Don't put yourself through any of the hell that is above that.
Did the for the 3rd time and first time without snow yesterday. This route really sucks quite alot and is one of the worst bushwhacks imaginable. I was surprised at how much thicker the brush is in the summer and the poison ivy is EVERYWHERE! That said, it really should be considered a must do for the avid Flatiron hiker. The tunnel is cool and there is a neat upper tunnel as well. You're guaranteed total solitude and it is hard to feel so removed from people and this route totally does it. Do it, you know you want to.
EDIT: Don't use this for a climber's approach/descent unless necessary. There are MUCH better ways to go for almost everything around. We don't want a social trail forming up there now do we? ;)
Did this again to the top of Green Mtn. There was relatively deep snow for most of it and we were required to bust out the rope twice to pass sheets of ice covering slabs. This really is one of the most horrendous bushwhacks I have ever done. Maybe the snow complicates it, but pushing though bushes and crawling over fallen trees gets old. I'm pretty sure my buddy will never hike with me again after I recommended this! Haha. That said, this really is a great exercise in negotiating horrid terrain.
downclimbed through the tunnel after climbing the fourth. yeah, there is a good bit of bushwhacking, but that's pretty mild, and a doable descent route, compared to the adjacent terrain. i'll use it every time.
Went to the top of Green Mountain. Was pushing through waist-deep snow in places and it began to be very demoralizing. The tunnel itself is very cool but most of the route above is a brushy nightmare. Go do it!