"Mount Osceola is named for the legendary Seminole chief who waged war against U.S. troops during the late 1830s when the government tried to move his people from Florida to Oklahoma. He died in prison in 1837. He never visited his namesake peak in New Hampshire. In fact, it was likely not named for him until late in the nineteenth century. The reason is unknown. A map of the region, circa 1860, refers to it as “Mad River Peak.” Mount Osceola is the highest mountain in the Waterville Valley area, dominating the northwestern end of the valley.
There are two approaches to the summit, one from Tripoli Road in Thornton Gap and the other via the Greeley Pond Trail and East Osceola, a 4000-footer in its own right. The Greeley Ponds are a high-use area. In addition, there is a “chimney,” a non-technical vertical climb between the lower, tree-covered East Peak and the main summit of Osceola, making this route doubly un-dog-friendly. If the main peak of Osceola is your goal, the approach from the Tripoli Road is more direct and definitely preferable with a dog."