These are 2 mountains that are 4000ft+ in height with a prominence greater than 200ft. This qualifies both of these mountains for the AMC New Hampshire 48, New England 67, and the North East 111 hiking challenges.
Summary
Alltrails describes the trail as "Get to know this 8.3-mile out-and-back trail near Waterville Valley, New Hampshire. Generally considered a challenging route, it takes an average of 5 h 24 min to complete. This is a very popular area for backpacking, camping, and hiking, so you'll likely encounter other people while exploring. The best times to visit this trail are April through October."
Stats:
Distance: 8.3 miles
Difficulty: Hard
Elevation Gain: 2851ft
Route Type: Out and Back
Average Time: 5hr 24 min
Story:
I would definitely recommend getting to the trail head early. This is a very popular mountain! I got there at 8:30am on a Thursday and the parking lot was almost full. While the parking lot is small parking is allowed on the road just follow the signs because you are only allowed to park on one side of the road. This trail is also very rocky so ensure you have proper foot support. On the way to the first summit (Osceola) these dogs and their owner passed me and one of the dogs was ahead of the group of its owners and thankfully the dog and myself are friendly. The dog come running up and stops to sniff me and I pet her. SO CUTE. However if I was someone who is afraid of dogs or allergic this interaction would not be ideal. Dogs are allowed off leash on most of the trails. While you can peer through the trees and start to see the view Osceola has it offer, it was interesting heading up especially closer to the summit. If it rains anytime soon that you are doing this hike be prepared for mud areas and wet rocks. There small streams of water that run down the rocks on the trial. But once you reach the summit of Osceola you will see most of the area. You can see Waterville valley ski resort, squam lake, and the surrounding mountains (too many to name). As this being a popular mountain expect to see many people on the trail to Osceola and at the summit. The trail from the trailhead to Osceola summit is ranked Moderate. The difficulty increased over the one mile hike to East Osceola. Quite a few of the reviews for this trail say "save some energy for east Osceola" or "it is the same climb to East Osceola as to Osceola". This route is more difficult due to the chimney climb. Now you do NOT need to do the chimney climb and I would not recommend doing the chimney climb down. I made this mistake. There is a bypass trail going down the left side if heading to East Osceola. When I went down the chimney my pack got stuck on a few occasions and the footing is so slim I could barely get myself unstuck. There are some rocks on the trail where you can get a view from but there is no view from the summit on East Osceola. There is a pile of rocks noting the summit. Once you reach the summit of East Osceola you just came back the way you came. I would recommend climbing up the chimney. you get a nice view from the top and I found it a fun climb. I stopped at the top of Osceola again on my way down to take in the views one last time. Again if it rained anytime near your trek of this trial beware on the way down of slippery rocks. I slid a few times coming down. Thankfully no severe injuries but injuries could result in any slip while hiking.
As always be prepared, check the weather, and get exploring.
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