My initial plan is to leave friday at some point, maybe morning or late morning - return monday at some point. I do have some flexibility on either side of the weekend, thur-tue if some one wants to extend a day here or there to hit up another trail or route…
The plans below are loose. I wasn't going to have to be anywhere at any particular time with the exception of the first night I definitely wanted to stay near st elmo to do a little poking around. The maps below are poor, but I do have detailed books for most of the off road portion of the trails.. which is the majority of the trip (except 285)
Friday
Leave Denver (time unknown) travel 285 to Buena Vista and up past St. Elmo. Depending on the time of day setup camp past St. Elmo on the road up to Tin Cup Pass. If there early enough enjoy the area, there are some great little lakes up there. Maybe explore up a trail or two or just chill out and cook a great meal.


Saturday
Continue up over Tin Cup pass down into Tin Cup itself and then around Taylor Reservoir to the north end of the valley and head up over Italian Pass. This is a very scenic route and at the pass you have th option to climb up to American Flag mountain to the summit.. and take in the sights. There are a few old cabins you can explore on both sides of the pass. After some sight seeing and maybe some lunch head down toward Crested Butte and camp along cement creek road or another area near Cement creek road. Again depending on the time of day and where we are camping explore a bit take in the sights good food.
Tin Cup Pass: http://www.traildamage.com/trails/index.php?id=120

Italian Creek: http://www.traildamage.com/trails/index.php?id=117

Sunday
Head down Cement Creek road into crested butte. Grab some breakfast or an early lunch. Lots of options here but my initial thought was to head over Pearl Pass and either continue on to Aspen via Richmond Hill Road which takes you basically to the top of Aspen Ski Resort. Then if the road through Aspen Ski resort is open (Aspen Mountain Rd) drive down the ski resort right into town.
Cement Creek: http://www.traildamage.com/trails/index.php?id=397
Pearl Pass: http://www.traildamage.com/trails/index.php?id=119
Richmond Hill: http://www.traildamage.com/trails/index.php?id=398
Aspen Mountain Road: http://www.traildamage.com/trails/index.php?id=399

or
camp somewhere in-between aspen and crested butte, explore the area - a few trails and sights around… then head down into Aspen on monday morning..

Check out the fullsize above map here: http://www.almostmadeit.com/g/galleries/Misc_Photos/CrestedButte-Aspen.jpg
Monday
Kind of a pot luck day...
Head up out of aspen over independence pass and head over Mosquito pass, Weston Pass or take Lenhardy Cutoff - all of which leads to FairPlay/285 then home.
Mosquito Pass: http://www.traildamage.com/trails/index.php?id=41
Weston Pass: http://www.traildamage.com/trails/index.php?id=110
Lenhardy Cutoff: http://www.traildamage.com/trails/index.php?id=434
None of the above is absolute or even that hard. I wanted to keep it loose and fun - If i saw something and wanted to stop or if I heard of another trail or road then maybe that could be an option. This was just a loose idea that could be a fun adventure.
I'm open to ideas and suggestions, I have been up to St Elmo (but not across the pass) and have been over Italian Creek/Pass so the rest was new to me.
Let me know your thoughts or if you want to come along - i like to wing it too but always wanted to do pearl pass into aspen