Getting ThereMT. OSCEOLA TRAILHEAD VIA TRIPOLI ROAD: (2280') This road is usually closed from November to April to snowmobile traffic. From I-93, get off on Exit 31 (Tripoli Road) and head east on Tripoli Road to past the trailhead on the Mount Tecumseh Trail. Mt. Osceola is 7 miles on your left (WMNF Mandatory Fee).
From Waterville Valley, head to the Waterville Ski Area. When you reach Tripoli Road make a right. When you come to a fork in the road, make another right. Head Past the Livermore Park Ranger Station and campground and all the way up Tripoli Road past the height of land. Mt. Osceola will be on your right just past the height of land.
KANCAMAGAS VIA GREELEY PONDS TRAILHEAD: Take I-93 to Exit 32. Take a left off the light at the exit ramp and stay on the Kancamgas Highway through the tourist town of Lincoln and past the Loon Ski Resort. continue past the trailhead to the East Pond Trail and until you begin up a switchback on the Kancamagus Highway. The Greenley Ponds Trailhead will be on your right.
Red TapeWMNF Mandatory fee at both trailheads.
When To ClimbMt. Osceola is usually climbed in summer and fall due to road access and the mud and black fly season in spring. Often though many people at a time will be on top of Mt. Osceola on summer weekends. During this time of year, Mt. Osceola would be best for new peakbaggers trying to get a taste of the 4000 footer's in the White Mountains
However Mt. Osceola can be climbed at all seasons. From Tripoli Road this hike though is dramatically extended in winter due to the closing of the road. Even with the closing of the Tripoli Road in winter this side can be climb by aid of only snowshoes due to its easy to moderate slope, although very long. From the east though crampons are very strongly advised due to a number of very steep sections on the trail.
CampingMt. Osceola can be easily done in day so there is little reason to camp while hiking the mountain. However if you like to do backcountry camping check out the Backcountry Camping Rules in the AMC White Mountain Guide (See Books).
There are also camping areas along Tripoli Road that only require a permit from Livermore Ranger Station and Livermore Camping Area nearby..
Mountain ConditionsHere are two websites that will provided you the best information on conditions in the White Mountains.
Appalachian Mountain Club
Current Trail Conditions
Also drop by the Livermore Park Ranger station in Waterville Valley for more information.