|12978 ft / 3956 m
Woolsey is certainly worthy of being one of the coveted 13ers in Wyoming, but alas falling short by 22 feet, Mt Woolsey remains, if nothing else, somewhat obscure. It is however, a NO WALKUP peak whose easiest route is 5.6. The setting is other worldly and the peak with its intimate view of the spectacular Innominate makes it a must do climb.
You can approach Woolsey from the north or the south. The northern approach from Big Horn Reservoir is long, scenic and worth the effort. There's a bit of a thrash getting into Penrose Canyon above Princess Falls, but other than that it's a wonderful journey in and of itself. From the south the approach is much more strait forward and can be accessed via Misty Moon / Cloud Peak and then after some cross country travel, a herd path into Wilderness Basin. This approach is not at all difficult. Your intuition should suffice. Get yourself to the Cloud Peak highcamp, then traverse west without giving up too much elevation as you slowly wind your way into Wilderness Basin. Travel in WB is both beautiful and quite mellow. You can get to the upper basin in a day and a half without too much effort.
There are several routes on Woolsey, but unless you're looking to do a first ascent, the one to do is the South Ridge. The orginal ascent in 1933 is an interesting read in the AAC journal. http://publications.americanalpineclub.org/articles/12193417000
That being said, if you are willing to put in the work to get yourself to the base of the route, then a little beta found here is yours courtesy of those of us who have been there. Keeping route info "on the low down" is a selfish attitude. Not many people are going to do this route. Sharing is paying it forward. A full trip report (without giving too much away) can be found at woolsey-s-ridge-aug-2019
If you have any questions etc, you can reach me at MLT contact form. Hint: the captcha answer, in case you aren't sure is "Warren Harding" - the original mavarick climber.
There is no red tape to climb in the Bighorns. There is no signout box at Bighorn Reservoir while there is one at Misty Moon on the south side of the Cloud Peak Wilderness. Other than that, you're good to go. In case you need directions, get a copy of Beartooth Publishing Cloud Peak Wilderness map. It covers the entire region. For the northern approach from Sheridan take rt 26 west and then eventually rt 293 south to Park Reservoir. From there it's a short but rugged 2 miles or so up to Bighorn Reservoir on rt 289. It's definitely high clearance only vehicles so buyer beware.
This is northern Wyoming so the season ain't at all like it is in the High Sierra. July to Sept is much like it is anywhere else in the Norther Rockies. You take your chances if you go here in Sept. But, it could be perfect and it certainly will be bug free if you go later in the season.
Great camping can be found on either of these approaches. A campsite in Highland Park on the northern approach is sublime. The choices in Wilderness Basin are endless.
No one other than Sarah @ 13er girl has published anything with regards to Woolsey. You can find her interesting and fun to read trip report @ Feelin' Alive on the Wyoming Thirty-Five