Trip report

Mt. Osceola Hike

Hiking - Full Day DATE: 10/03/2026 - 10/03/2026

Trip/Event Location: Waterville Valley, NH

Trip Leader(s): dpbyrnes

Max # People: 10

Trip Guiding / Event Fee: No, I will not be asking participants for money

Difficulty Level: Moderate to Strenuous

I’ve been wanting to do Mount Osceola (one of New Hampshire's great 4000-footers IMHO) all summer and now I am going to be out of town on10/24 so will miss the GO trail maintenance day. So, for ...
Driving directions to the location and spot to meet at: I-93 North Take Exit 28 in NH towards Waterville Valley. Turn RIGHT onto Route 49 East for 10.2 miles Turn LEFT to the access road for the Waterville Valley Ski Area for 1.3 miles Turn RIGHT to Tripoli Road [dirt road] and follow for 3.2 miles where it crests at the 2,300-foot pass About 200 yards beyond, the Mount Osceola Trail enters the woods on the right, where there is parking area. However, you will most likely park alongside the road and short walk to the kiosk where we will meet.
Trip Report/Photos

Excellent views to enjoy on this stellar weather day. I only hope the trail maintenance day is just as nice.  I’ve never seen so many cars parked on the road before, it was a popular day for this hike.

The four of us started from Tripoli Road around 9:20 ascending to the summit of Mt. Osceola. There we a large number of hikers coming down (maybe 40-45) from a sunrise hike- they started at 4:30am! Overall, we met probably 75 friendly hikers and a number of dogs for the day - lots of nice views. And there was vista of course. ?

We reached the summit in a few hours and then proceeded onward to East Osceola where we had lunch and chatted with some folks.

It was a perfect fall day, and the trees changing color were beautiful. We’re definitely a few weeks behind in the turn of foliage down in Mass. 

Going in our direction the Mt Osceola Trail is a pretty easy though there are some tricky 45-degree rock climbs and the trail can get tight in places.  The real challenge is getting to the East Peak.  Very steep in places especially one section called the chimney.  But that was actually fun to climb back up on our return to the main summit (and one does feel a measure of pride for tackling it).

Back to the parking by 3:45. Great hiking day. 

  There are 6 photos in Album (Note: Move mouse pointer over larger pic and click on NEXT for better viewing)

Members That Participated

dpbyrnes

Outdoor Fitness Level: Moderate to Strenuous


Ipswich, MA


United States
MO

Outdoor Fitness Level: Moderate to Strenuous


Lancaster, NH


United States
baezfred

Outdoor Fitness Level: Moderate to Strenuous


Lancaster, NH


United States
Helvetic Hiker

Outdoor Fitness Level: Very Strenuous


Barre Town, VT


United States
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