Black Pin Hikes
This chart shows what I consider some of my toughest day hikes, but not all the black pin hikes. It shows the elevation profiles for each one in an easily comparable way. I got this chart idea from HikingGeek.com. For full details of each hike, see the associated trip reports. I decided to stop trying to rank the relative difficulty of these trips, other than to say that Tanriverdi Falls stands alone as my toughest day hike so far.
Tanriverdi Falls - A canyon hike leading to the largest waterfall in the Santa Ana Mountains. The first half of the canyon has a good use trail, but when you reach the second falls, it is totally wild. There are eight waterfalls that must be bypassed in the canyon to get to Tanriverdi Falls. On the way, you will face ticks, a forest of unavoidable poison oak, and difficult and dangerous navigation on the sheer canyon walls. While the stats look tame, this is the most dangerous hike I've done. I could only manage about 1/2 mile per hour in the technical mid-canyon section. Better for canyoneers than hikers, rarely visited. Not the same kind of challenge as long distance/gain on a trail. Bring your war face.
Cloudripper - The highest summit of the Inconsolable Range in the Eastern Sierra at 13525'. Starting at South Lake and heading toward Green Lake, about half of the hike is off trail boulder scrambling. You have to go over Vagabond Peak at 13347' or nearly over it to get to Cloudripper on this route. Both summits require some exposed class 3 moves to reach. The constant exertion at this elevation is a real grind. As much a mental challenge as physical.
Mount Whitney - The main Whitney Trail starts above the summit of Big Iron Mountain (Angeles National Forest), and it is all about altitude. Gaining over 6000' is not the hard part, but spending 8 of the 22.5 miles above 12000' is. Every step higher means less oxygen available to your body, and at the summit of Mt. Whitney, you only have about 59% of sea level oxygen. My body starts to feel the lack of oxygen around 9000'. This can be mitigated by properly acclimatizing before starting the hike, but there are no guarantees.
Cactus to Clouds - A famous 20 mile hike, known for the punishing gain from the desert to the top of Mt. San Jacinto. My GPS measured the gain at 10614', about two vertical miles. During most times of the year, there is a severe risk from the heat unless you start in the middle of the night. The weather 10000' up is quite different from the desert floor. On my trip, there was snow from Mountain Station to the summit where cool temps and strong wind made for wind chills in the 20s (Fahrenheit).
Cobblestone Mountain, Sewart, White - Probably the most remote peak in the Los Padres National Forest, Cobblestone has the profile of a canyon hike. You go up and down in 1000' spurts. It takes more than an hour just to navigate the dirt roads to the Buck Creek trailhead. Due to past fires, deadfall blocks the trail for miles at the beginning and around White Mountain. Navigation was hard and you can expect to make a few mistakes getting up and back. From the ridge to Cobblestone is practically cross country. Like Iron Mountain, there is no water anywhere. I packed in 248 oz (7.3 liters) and needed every drop. The final 1000' slog up Sewart at the end was brutal. This hike left me with a deep bone bruise in my hand that took 5 months to heal and I lost a toenail on my right foot. If you want to practice a similar, but much easier version of this hike in the San Gabriels, try Twin Peaks East and West plus Waterman Mountain.
Grand Canyon South Rim to North Rim - Heat, heat, and heat. This is an inverted mountain with most of the work at the end. The key thing is to mitigate the 100F+ temperatures in the inner gorge by being past it before midday. There are plenty of amenities and water along the trail, but managing your hydration and electrolyte balance requires attention. There are also logistical problems getting around the canyon when you are done. Once you mitigate the heat and deal with the logistics, it is just a simple 24 mile hike with 6000' of vertical gain.
Pyramid-Villager Loop - A harsh desert, canyon scrambling, cross country, waterless, ridge roller coaster...in the dark. As a pure desert hike, this one can only be attempted in the winter. Winters mean short days, and unless you are very fast, that means at least a few hours of this hike must be done in the dark. I started an hour before sunrise and ended three hours after sunrise. The 19.2 miles and 7107' of gain took me 14 hours and 45 minutes. Only Mt. Whitney took me longer. The big 1000' dip between Mile High Mountain and Villager near the end of the hike was the crux. I also ran out of water and was very dehydrated at the end. It's hard to guess exactly how much water you'll need, but there is nowhere to refill if you run out.
Big Iron Mountain - My baseline for tough day hikes. With a summit of 8007', you don't have the altitude issues of other hikes, but it is steeper than most with plenty of loose dirt. The descent is also brutal. I fell a number of times on the way down and shredded my shorts. They ended up with several holes in them and I had to throw them away after the ordeal. Another difference with the other hikes is that there is no water available along the trail. You must pack in everything you need, which was 224 oz (6.6L) for me.
Here are the same hikes showing the elevation profile assuming they all started at sea level:
Tough Red Pin Hikes
Following are some hikes that didn't rate black pins, but were very tough, strenuous hikes. I suggest getting armored up physically and mentally before tackling any of them. These are in no particular order as far as difficulty.
San Gorgonio from Vivian Creek - This hike to the highest peak in Southern California is over 17 miles round trip with over 5000' of gain and high elevation. A tough hike and I think one of the best Mt. Whitney trainers.
Cucamonga, Big Horn, Ontario - Sometimes, Etiwanda Peak is thrown into this mix (CEBO). I added a twist (and saved distance) by heading cross country up to Big Horn from the Cucamonga-Big Horn saddle. This hike was very memorable for me because it was the first time I encountered a herd of big horn sheep in the wild.
Indianhead - This hike in the Anza-Borrego Desert State Park looks like a low elevation cakewalk, but only about 2 miles of the 9 mile round trip are on a trail. Be ready for some route finding, large boulders and class 2/3 sections on exposed ridge lines. Oh, and expect close encounters with a dozen varieties of cactus and yucca. I bled quite a bit on this hike and getting down is every bit as hard as getting up.
Goat Canyon Trestle, Piedras Grandes, Puff BM, Moan BM, Indian Hill - This is a long, cross country, boulder hopping heaven with more of what Anza-Borrego does best. Serious route finding, cactus, yucca, and no water. The up side is you get to see one of the longest wooden train bridges anywhere. The structure is breath taking, and even if you don't want to do the full loop, just getting to the trestle and back is no easy task. Like Indianhead, expect to bleed.
Marion Mountain 5-Pack - Long climb up the Marion Mountain Trail, then cross country to 10000'. All five peaks are off trail. All have class 2 summits except Marion at class 3, but the granite is of the finest quality. I made this harder than it had to be by leaving the trail at a place that was not ideal. Regardless, this is a lot of work at high altitude. For a greater challenge, you can pick up the rest of the San Jacinto 10000'+ peaks.
Technical Hikes and Rock Climbing
These hikes range in difficulty but had some kind of technical component or rock climbing that required gear, a rope and/or advanced techniques. I am not sure they fit into the general difficulty scale because they use a different skill set. In all of these hikes, it was just the summit block was technical.
North Iron Mountain