Mt. Osceola and East Osceola

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Raymond: and an undetermined amount of miles from the starting trailhead via road.

However, I really enjoyed the hike with short car shuttle from Waterville Valley gradually ascending the upper end of the Mad River and passing the Greeley Ponds (a White Mountain must see) and then traversing the Osceola Trail by ascending East Peak & Osceola and descending to Tripoli Road. The climb up East Peak is tough but also quite enjoyable. For me it brought back great memories of my first White Mountain trek in 1971.

Personally, I feel you are really missing the Whites if you just climb the peaks the quickest and shortest possible route. If you don't have time to do the whole traverse, maybe you should reconsider this hike and do a hike to Sandwich Dome from Waterville valley or a leisurely trek over Welch & Dickey. This is just my opinion and might not be acceptable to some. But there are alot of sites out there in the Whites besides 4,000 footers worth seeing.

Here is my photo album from my Osceola hikes.
 
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Osceola's & Tecumseh Loop

I know the original question of this thread was regarding info. on the quickest way to bag the Osceola's, but here is a loop I like, that might be of interest to the folks that want their hike to take more time than their drive to & from the Whites. It goes over the top of 3 NH 4's & is approx 17 miles in length.

Park at the same parking area for Greeley Ponds / Livermore Rd in Waterville Valley. I like to leave the Greeley Ponds trail section for last, so head out to the Tripoli Rd, turn right & go just a short distance & on the left you will see the Pipeline trail, which is a ski / bike trail that connects Tripoli Rd to the base of the Waterville Ski area.

After summiting Tecumseh, continue West on the Mount Tecumseh trail & down to Tripoli Road. From there it is 1.2 miles, at a slight up hill pitch (South/East or Right) to the Mount Osceola trailhead. Up & over both Osceola's & down to the junction with the Greeley Ponds trail, and then back (right) out to the parking area.

No car spotting required, and it is very easy to stash extra water at either of the Tecumseh or Osceola trailheads on Tripoli Rd.
 
I didn't know the Pipeline Bike/ski Trail existed. That is a loop I'll have to return to do. I just don't know if I like the idea of descending to the east off of East Osceola. I might want to do the circular in reverse. Is it hard to find the terminus of the pipeline trail at the Tecumseh/Waterville Valley ski area?
 
Finding the Pipeline trail at the Ski Area

WV is good at keeping their trails signed. Their x/c & bike division has personal out on the trails regularly, and there are trail maps posted at most intersections I've found.

If you drive directly to the ski area first to scope out where to pick it up, once you arrive at the counter clockwise parking network, bear right as if to head towards the Mount Tecumseh trailhead. Immediately upon making this right, you will see the Pipeline trail sign on the right (it looks like a grassy road non-winter).
 
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