Chicago Basin to Mount Eolus is a 18.4 mile heavily trafficked out and back trail located near Silverton, Colorado that features a lake and is rated as difficult. The trail is primarily used for hiking, rock climbing, camping, and fly fishing and is best used from July until September. Dogs are also able to use this trail.
Windom peak was my first 14er. We rode the train from Silverton to the trailhead. Buy tickets in advance! Small town but free parking unlike Durango. Hiked to base camp - lots of sites but it can be crowded for a reason. So beautiful with many waterfalls and accessible water along the way. I carried 2 liters but could've gotten away with 1 bottle. We summitted Windom and saw how crazy the others looked so we went back to base camp in the rain and took a rest day the next day. Met amazing people and followed the creek for photography shots. The day after that we hiked out. The elevation is what makes this so hard. That and all the rocks you have to rock climb so put away those hiking sticks when you get past Twin Lakes. It was chilly at night dropping below 30 but we had enough gear and food. Lots of deer. Strangely we didn't see any mountain goats but heard they are normally so persistent that you have to pee on rocks and pack out #2 & all TP in bags that they give for free at the register box.
I summited Windom Peak in July of 2009 with a group from my high school. There were 12 students and 2 teachers, with student experience ranging from basically nothing to climbing at the local indoor climbing gym, to small excursions to places like Devil's Lake (in WI). My experience was only the indoor climbing gym and small, simple hiking excursions around my hometown. We took the narrow gauge train from Durango to the Needleton stop, which was basically a clearing in the forest. We camped in the Chicago Basin, which was about a five hour hike from the train stop including a lunch break. We woke up at 4:30 AM the next morning and began our hike to the summit. We reached the summit around 11 AM and headed back shortly after-about 12 hours round trip. Although I can't say much about the route we took, I can definitely say this is not for the faint of heart. It was quite a workout, but well worth it. Of the 14 of us that started out for the summit, 12 reached the top; the two that didn't summit suffered from altitude sickness or a fear of our height. So minor experience is okay, but only if you have experienced guides and are in good physical condition. The most difficult/technical part of the climb was sort of bouldering, but basically scrambling up a pile of rocks-not difficult, but also not a walk in the park. Overall this was a wonderful challenge.
Also, I only summited Windom. There are two other peaks very close by and it is possible to do all three in one day.