This trail was hiked and written up by Heather Cote

The Waterville Valley Skyline Loop is a challenging New Hampshire hike, covering 15 trails and nine peaks. The entire loop is roughly 34 miles long and has about 10,150 feet of elevation gain. This is not for the faint of heart, but the rewards are worth the effort.

Region: New England (White Mountain National Forest, New Hampshire)
Distance: 34 miles, 2-4 days

Physical Difficulty: Difficult

  • Weather changes in the White Mountains must be monitored
  • Rocky climbs for the ascents of Mt. Tecumseh, Mt. Osceola, East Osceola and North Tripyramid.  
  • The slides on North and South Tripyramid should be navigated with care only in dry conditions.
  • Cumulative elevation makes for near continuous climbing


Logistical Difficulty: Easy

  • Livermore Trailhead provides a perfect spot for either a one-day trip or multi-day trip. Using a car as a midpoint allows hikers to carry less gear if they desire.
  • No resupply options – pack what you need in your car.
  • No permit required; however, parking must be paid for at Livermore Trailhead if you do not have a White Mountain National Forest parking permit ($5/day at the iron ranger).

Season: Summer, early fall

Elevation (average): ~2,500 feet
Total Elevation Gain: ~10,150 feet


Hiking the Waterville Valley Skyline Loop

The Waterville Valley Skyline Loop is not comprised of new trails; in fact many of them can be found in the Appalachian Mountain Club White Mountain Guide.  The Loop strings together trails from the AMC guide, Waterville Valley cross-country ski routes, and Tripoli Road.  The intention of the established loop is to bring hikers to the Waterville Valley area, a less popular area than Franconia Ridge or the Pemigewasset Wilderness. This area also doesn’t get as much attention from hikers as the Presidentials to the northeast.  While this is a quiet, desirable feature of these trails and mountains, the community is eager to share it with others.

I have hiked the Skyline Loop in a variety of ways. I did this intentionally so I could experience it from both the overnight hiker and day hiker perspective. This loop is traditionally hiked clockwise starting with Mt. Tecumseh. I never hike without checking the mountain weather forecast from a variety of sources, including the National Weather Service Recreational Report for higher summits. Since these peaks are in the 4,000-foot ballpark, this forecasting is reliable. That said, prepare for all weather conditions in the Whites regardless of season. My kit includes rain layers, warm layers, hat, and gloves … even in the summer. 


Overnight Trip on the Waterville Valley Skyline Loop

I gathered a few friends for a 20-mile backpacking trip of the west loop. The weather forecast was for the 60s during the day and high 40s at night.  We started at the Livermore Trailhead and headed to Mt. Tecumseh by taking the Pipeline Trail to the Waterville Valley Resort and the location of the Mt. Tecumseh Trailhead.  This mountain is frequently hiked.  The trailhead has received a lot of work over the years, which includes the installation of the longest set of stairs I have ever seen.  We summited, had a snack and headed down toward Tripoli Road.  We were banking on refilling our water at the brook near the Tecumseh Trailhead at Tripoli Road and were rewarded with a flowing stream, despite dry conditions.  We loaded up knowing water would be scarce until the Greeley Ponds area.

We headed east on Tripoli Road for just over a one-mile dirt road walk.  I was surprised to pass open campsites along the road on this busy Saturday in August.  These are first-come, first-serve spots that would make a great camping option for this area if you don’t want to deal with White Mountain National Forest Backcountry Camping Rules. If you plan on staying on Tripoli Road, make sure you check in with the caretaker and pay the fee. This area can be challenging to tent camp due to the terrain. Hammock campers will have an easier time setting up and following the strict rules. Other camping options include Osceola Vista Campground on Tripoli Road. This campground has a combination of reservable and first-come, first-serve sites. The same goes for Waterville Campground, a short drive from this area.

Our hike up Mt. Osceola was gradual and comfortable with an overnight pack. The open summit is 2.9 miles from the trailhead and easily one of the best vistas on this hike. We took some time for a snack before heading over to East Osceola.  You will descend the famous chimney between the peaks.  On this day, we chose the bypass because we had overnight packs.  We made short work of this section and summited East Osceola quickly.  This treed-in summit has a cairn to signify the top.

The descent down the Mt. Osceola trail to the Greeley Ponds Trail is steep and unrelenting for just over a mile—in some spots the grade is over 25%. The trail eases up substantially as you come into the Greeley Ponds Scenic Area.  We hooked a right onto the Greeley Ponds Trail looking for flowing water. We passed by the Greeley Ponds, considering filtering from here but decided to take our chances on hitting flowing water at Mad River. We were thrilled to see the water was flowing nicely a few tenths of a mile south of Lower Greeley Pond. We stocked up for the night and set to work locating our camping location for the night.  We set up off the Greeley Ponds Trail, in keeping with backcountry camping principles, a few miles from the Livermore Trailhead, making for an easy walk out in the morning and a total of 20 miles for the west side of the Skyline Loop.


Tripyramids

There is such versatility with this loop. Livermore Trailhead makes a perfect spot for resupply if you plan on doing this in two-plus days. You can also hike part of the loop from this lot. The Tripyramids are a staple for any Northeast hiker checking off their 48 4,000-footers. The Skyline Loop recommends use of the Scaur Trail, giving hikers a gentle ascent to access North Tripyramid.  If you are feeling adventurous, take the detour and do the North Slide.  Be prepared for hand-over-hand climbing and tricky rock wall navigation.  You will be rewarding with breathtaking views and a badge of honor.  DO NOT attempt North Slide if it’s raining or the slabs have a chance of being wet.  Also, do not go down North Slide.  To follow the loop on the map, go up Scaur Ridge Trail to North Tripyramid, travel across the relatively tame and treed ridge walk and down the South Slide.  South Slide has a fair amount of scree, but it is manageable and short.


Kettle’s Path, Irene’s Path, Old Skidder Trail and Snows Mountain

I had not seen this section of the trail before preparing to write this article, and I will certainly go back. I parked at Livermore Trailhead on a beautiful Saturday, and I was surprised to not be sharing these sections of trail with another soul. I took all side trail options, which gave me a breathtaking view of Waterville Valley from the Scaur. I also visited the Flume Spur off the intersection of Irene’s Path and Old Skidder Trail. The water must rage here in spring and the rock chimney is worth checking out. Old Skidder Trail is not used much, so just a faint footpath remains. This entire area is connected by a system of “roads.” Essentially these are carriage roads used for mountain biking and cross-country skiing.  After exploring these sections, I filtered water from Slide Brook and took the carriage road over to get on the Snows Mountain Trail, then hiked toward Snows Mountain clockwise. My ascent was nearly 1,000 feet, and the summit has an overgrown outlook, but if you continue clockwise on your descent, you will come to a second outlook over Waterville Valley.  Heading down this way was much tamer.


How to get to the Waterville Valley Skyline Loop

Nearest Town: Waterville Valley

Located off Tripoli Road, Livermore Trailhead is prime for accessing this area.  Waterville Valley is a quaint town, with coffee shops and a country club.  The mountains and skiing are a major draw in this area.  Note: Tripoli Road is closed in the winter, so Livermore Trailhead may be accessed through the village of Waterville Valley.


When to Hike the Waterville Valley Skyline Loop

Fair weather hikers will want to stick to the warmer months of late May through early October.  Year-round hikers, with proper gear, including snowshoes and microspikes, will be able to enjoy some of these trails.  Enjoyment in the winter is limited by your interest in properly breaking trail in snowshoes, and experience is necessary. Please do not walk down the middle of the groomed cross-country trails in the winter!  

In clear weather, hikers will be rewarded with amazing views of the Whites.  As always, check the weather forecast (see below) and turn around if conditions deteriorate beyond your ability to stay safe. 


Waterville Valley Skyline Loop Terrain 

The bulk of this loop is classic White Mountain National Forest terrain.  Rocks, roots, and slabs dot most of the trails. The cross-country trails are a nice break on the legs. I always say the Whites are not for the faint of heart, so be prepared to work for all of your elevation gain, especially with a heavy pack.


Logistics: Permits, Camping, Water and Gear

Permits:  The Waterville Valley Skyline Loop is located in the White Mountain National Forest.  A permit for parking can be obtained ahead of time.  Otherwise, pay the $5 at the Livermore Trailhead parking lot.  The same goes for other lots located on this loop and managed by the WMNF.

Camping: While camping is permitted, you must follow White Mountain National Forest Backcountry Camping Rules. The terrain here is brutal for tent camping. Rocks and roots making finding a flat spot nearly impossible. Experienced backpackers may find a place to camp around 2,500 feet in some places.  Hammock campers will do best on this loop.  Established camping areas in close proximity include:

Tripoli Road Camping Area. Fee required and may be sold out early in the day in the summer.

Osceola Vista Campground

Waterville Campground

Water: Water is plentiful despite the moderate drought in this area in 2022.  While it looks clean and is flowing, filter or treat it! I carried 1.5 liters most of the time, filling up with extra at Mad River for the overnight.  You will not find water up high (over 2,000 feet in most places), so grab water when you can. 

Special Gear: 

  • Poles are invaluable in this terrain
  • Paper map and Gaia GPS with downloaded maps.
  • Ten Essentials for Hiking

Know Before You Go

Waterville Valley Recreation Department did a great job stringing together existing trails to create an adventure for day hikers and backpackers alike. I was impressed with how quiet the eastern side of the trail was (with the exception of the Tripyramids). I love the versatility of the trail system in that it provides day and overnight options if you plan well.  

Resources

Waterville Valley Skyline Loop: Information and map 

White Mountain National Forest Camping 

National Weather Service Recreational Report: For the White Mountains

Hiker friendly campgrounds:

Osceola Vista Campground 

Waterville Campground

Tripoli Road Camping Area

Appalachian Mountain Club White Mountain Guide and maps

Gaia GPS