Via the Greely Pond Trail and Osceola Trail 7.6 Miles Round Trip
Mt. Osceola and its East Peak are both considered separate four thousand footers on the New Hampshire list, coming in respectively at 24 and 34. There are two main routes of approach to hiking the Osceola peaks. One is easier; approaching from the Tripoli Road in the Waterville Valley area and the other which climbs the north spur is much rougher and steeper. This uses the Greely Ponds Trail off the Kancamagus Highway and connects with the Osceola Trail 1.3 miles from the parking area. Gaining first East Peak and then after 1 mile of ridgeline summiting Osceola. To return to the parking area, turn around and descend the same way to complete the more difficult of approaches. If you are new to hiking or you are unsure about your ability to handle difficult steep ledges do not attempt to hike Osceola from the Kancamagus side. This is a hike that dogs can do but only bring your dog if you are certain that you and it will be safe. It is extremely steep, ledgy and the footing is poor from East Peak to the Greely Ponds Trail on the Osceola Trail.
Parking for the Greely Ponds Trail is located off the Kancamagus Highway, it is on the left after the hairpin turn if arriving from the east. There is a fee collected at the site, although there are no facilities located here. It is also a rather small parking area, so while it is well signed and easy to find, on weekends it is frequently full early. The Greely Ponds Trail is very easy to follow. It is marked with yellow blazes for hiking and is crossed multiple times by a ski trail marked with blue diamonds. The footing is excellent; the grade is just above flat so extremely easy hiking. The 1.3 miles to the Osceola Trail junction is a breeze, and there is plenty of water for dogs along the way. At the junction bear right to follow the Osceola Trail for the summit of East Peak, but do not let the short distances fool you. While from the junction it is only 1.5 miles to the summit of East Peak it is a very grueling ascent.
The North Spur of Osceola ascends moderately at first, up a collection of stone stairs built by trail crews in the past. The footing becomes difficult as the trail climbs gullies of loose rock and scree. It becomes more challenging as you gain the cliffs of Osceola’s North Spur; these are visible as you ascend the trail. Here the trail becomes much more exposed, so use caution in inclement weather. There are several sections of ledges and slides, where the climbing is hard but the views are impressive. This is not a trail for inexperienced dogs and humans, but for those who are looking for a challenge with rewards it is an impressive trail. At the top of a small gully there is a lookout to the right with views of Osceola and surrounding peaks. From here continue on to the summit of East Osceola, marked with a small rock cairn.
From East Peak it is 1 mile to Osceola, which is visible straight ahead in the distance. This section of the trail is moderated by some flat stretches, paired with some rocky descents. As you approach Osceola there are a few sections that are more difficult with large boulders that need to be climbed using hands as well as feet. There is a steep chimney at the main pass between the summits that can be avoided by going to the left (I would recommend that most dogs avoid it). Compared to the ascent this section of the Osceola trail is much easier, and the summit of Osceola is gained relatively quickly.
The summit of Osceola has fine views that are unrestricted by trees. Mount Osceola is one the most climbed mountains in the Southern White Mountain region because of its easy approach from the Tripoli Road. Though Mt. Osceola never reaches timberline, the two views from the summit are spectacular. On any given clear, high visibility day you can see forty-one of the other 4000’s in New Hampshire and even faintly see Mt. Mansfield towards the west. There are remnants of a former fire tower on the summit, reminding us of a time when information traveled a bit more slowly. These concrete blocks now make excellent backrests or seats to enjoy a snack on before descending.
After enjoying the views turn around and go back the way you came. The descent from Osceola to East Peak is relatively easy, other than the section of chimney, again that can be avoided. However, the descent from East Peak to the Greely Ponds Trail is very steep and exposed in sections. There is loose footing, and in some places slippery rocks. Use extreme caution and take your time. This is one trail that took me almost as long to go down as it did to ascend. In conditions like these the dogs seemed to have the advantage of some extra appendages on the ground. They slipped around much less than I did. Once the Greely Pond Trail is reached it is a very easy 1.3 miles of nice easy walking back to the parking area.
Overall Osceola and the East Peak is a challenging day hike from the Greely Ponds trail junction. This can be avoided by doing Osceola from the Waterville Valley area off the Tripoli Road instead this is also a shorter route of 6.4 miles and more appropriate for new hikers. I would only recommend that experienced dogs and humans attempt Osceola from the Kancamagus and only on days where the weather is looking fair. The Osceola trail up from Greely Ponds will be more challenging in bad weather and no one wants to get hurt while hiking.
Parking area Trailhead Greely Ponds Trail to Junction Osceola Trail: 1.3 miles
Osceola Junction to East Peak: 1.5 miles (2.8 total miles)
East Peak to Osceola: 1 mile (3.8 total miles)
Osceola to East Peak: 1 mile (4.8 total miles)
East Peak to Greely Ponds Trail Junction: 1.5 miles (6.3 total miles)
Greely Ponds Junction to parking area: 1.3 miles (7.6 total miles)