A close second to the snowshoe debate is the controversial question of the hardest NH 4000 footers. I personally have been hiking the NH 4Ks since 2012 and have done each one at least four times and in every season (some with many repeats). This gives me a unique position to rank the 4000 footers with a bit more perspective. I haven’t hiked every single route to the peaks so this is of course the most challenging 4ks based on my own opinion and experiences.

The hikes included do not entail “death marches” like a full one day Presidential Traverse or single day pemi loop. They do include pairs of peaks commonly hiked together by someone with the intention of hiking the full list. These hikes are what I would consider my top 5 most challenging hikes and are not listed in any particular order.

1. Wildcats Traverse

Most hike the three Wildcat peaks from Wildcat Ridge and Nineteen Mile Brook trails which itself is extremely rugged and steep. One autumn (yes, the photo above was taken the second to last weekend in fall!) I was finishing my NH 4000 Footers in that season and decided to do a different route, climbing the three from Pinkham Notch. I didn’t know at the time, but the section from Pinkham Notch to Wildcat E is the steepest section of the entire Appalachian Trail (2000′ in 1.5 miles, with one 1000′ climb in 0.5 mile). ! I later learned about this from Guthook’s site.

That hike was particularly difficult because we broke trail the entire way through feet of snow. Each section usually entailed 3 steps forward, sliding backwards, and then going up again and really getting our snowshoe crampons into whatever solid surface we could find.

My first hike of the Wildcats was in the pouring rain which also makes the steep sections more difficult. No matter the route or conditions, the Wildcats are a difficult trio!

2. Jefferson

Of all the trail options on the Terrifying 25 list, five of the trails ascend Mount Jefferson: Caps Ridge, Castle, Six Husbands, Sphinx, and Castle Ravine.

There are many aspects that make Jefferson difficult no matter the route. From extreme weather on exposed trails to navigating through ladders, boulders, scrambles, and ledges- Jefferson always packs a punch. 

Caps Ridge is the easiest route of all the options and it is still a rough and exposed trail to the summit. The Six Husbands Trail is a fun route and at almost 15 miles, a full day of hiking.

3. Owls Head

lower section of Owl’s Head Path

Owl’s Head is notoriously left for almost last by most hikers checking off the 4000 footers. At 18 miles, it’s a long hike for a wooded peak. Overall it is a nice hike, but for many it’s their first overnight trip carrying much more gear than a typical day hike and staying in a wilderness campground. Owl’s Head is also the only NH 4K that involves hiking on an unmaintained trail and has the option for a couple of bushwhacks to save some mileage and avoid some larger water crossings.

4. Galehead and South Twin

I remember the first time I hiked down South Twin I was so thankful I wasn’t hiking the Twins from the opposite direction as it is exceptionally steep. I prefer snagging the Twins along with the Bonds (and also adding in Hale and Zealand) as a two day hike to get a bunch of peaks in for not too much more effort than just doing the Bonds alone. The climb up to South Twin from Galehead hut is extremely steep and lasts quite some time. The views from South Twin do make it worth the slog!

5. The Bonds

My favorite hikes tend to be the most difficult ones and it has to be for the effort-to-reward ratio. The Bonds are a 20+/- mile round trip hike. For that mileage you get a true wilderness experience, standing atop the summits without anything man made in sight. When I was working on the NH 48 in winter I actually burned the roof of my mouth because it was so cold out. Mouth breathing for 20 miles in one day in winter will do that to you!

There you have it- my personal opinion on the hardest NH 48 hikes! Are you just starting out? Here are my recommendations on 4000 footers for beginners!

I’d love to hear which of the NH 48 you’d say are the toughest! Leave a comment to let me know.

Last modified: July 29, 2019