Skyline Route

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Overview
The infamous Mt. San Jacinto Skyline Route (aka. Cactus to clouds, Chino trail, Outlaw trail) is known to some as the 5th most difficult and enduring dayhike in America. BLM (Bureau of Land Management) and the California Department of Forestry denies Skyline even exists because of the very frequent rescues and even deaths on the route. Marines have even been rescued from it. For experienced hikers, this route is a piece of cake and can be done in one day, with some fatigue in the end. In summer, people training for ironmans and marathons frequently use skyline. Even so, it is pretty much deserted most of the time. The reason why so many people have died on the route is because of the amount of inexperienced hikers and Sunday joggers from the nearby city of Palm Springs wanting to "prove themselves." Before attempting this route, it is highly recommended you meet the requirements written near the bottom of the page.
Stats 
Length: 16 miles one way, 32 miles round trip
Elevation Gain: Although the elevation of the peak of Mt. San Jacinto is 10,834 feet, the route gains 11,000 feet in elevation if you include all the downhill dips. That's a little more than one third the height of Mt. Everest.
Difficulty
When there is no snow on the ground (typically June through October) the trail is mainly easy to follow but at some points you may pause and wonder if you are on the right trail, some points may be strenuous, rated class 1 on the Yosemite Decimal System.When there is snow, you will need route finding skills. The stretch of area right before 8,000 feet requires class 3 climbing skills with an ice axe and crampons. It is very highly recommended that you hike the route at least once in summer before hiking it in winter. 
Time Required
Most people planning to do this route plan to do it in a day, but more than half dont reach the summit, get rescued, or end up having to camp somewhere. The average one way time (meaning from the start of the route to the summit) takes most people about 12 hours. The fastest one way time ever recorded is about 5 hours.
Location
The start of the trail is the Palm Springs Art Museum, the address is: 101 North Museum Drive
Palm Springs, CA 92262-5659. Drive to the back of the museum where there is a parking lot. There should be a trail with a sign reading "welcome to the museum trail."
Route Description
Locals usually divide skyline into a "4 part route" as is passes through 4 climatic zones. There is Lower Skyline, Middle Skyline, Upper skyline, and finally San Jacinto Peak trail.
Lower Skyline: This section is the first 4 miles and 4,000 feet of Skyline and is all desert terrain. There will be lots of cactus and desert shrubbery. The very first 0.7 miles of the route has many trails branching off and locating the right one may be tough to find. Many of them go for a little then disappear. It is strongly recommended that you check the area prior to your hiking day. At the end of the 0.7 miles you should see a flat area and some picnic tables. This is the end of the section locals call the Museum Trail. You should be at an elevation of around 1,200 feet. There should be two trails branching off in front of you. Take the one on the right. You are now on the official Skyline Route. For the next half mile after the tables, you should see numerous signs and spray painted rocks warning you how dangerous the route is and how people have died. These are mostly set up by rangers who are tired of rescuing people from the route. 3.3 miles after the picnic tables you are at the end of Lower Skyline, and at around 4,000 feet elevation. You may or may not see a pile of pebbles on the ground that form the number "4,000." The pebbles are constantly blown away in storms but people constantly put them back.
Middle Skyline: Middle Skyline is 3.5 miles long and gains a total of about 1,700 feet of elevation between the beginning to the end of the section, but you actually gain just under 3,000 feet. This is because the middle portion of skyline is a series of uphills and downhills. It will seem like you are not making any progress. In one area the trail suddenly dips 300 feet downhill after going uphill for over a mile. The desert cactus and grass that you have seen on lower skyline will give way to mostly coyote brush and a few small pine trees. The route gets greener and greener as you go up. In some areas the brush will be a bit thick and you may have just a little trouble locating the trail, but its not a big problem. Its a whole different story if there's snow on the ground.
Upper Skyline: This portion is the shortest but most difficult part of the route. It is 2.5 miles long, gains 2,300 feet and you end up in Long Valley at 8,000 feet. Snow is almost certain to cover this section in winter. The trail now will not look like a trail anymore, but like a path created by mules trudging on the same area of brush over and over. You will also notice the amount of tall pine trees start to increase. Its mainly the last mile of upper skyline that will really get to you. It gets steeper and steeper. In winter, the last mile involves class 3 climbing skills with ice axe and crampons. Be careful, this area is commonly covered with ice. If you fall, there is no way of stopping yourself from going down the 60 degree angle slope for a vertical 2,000 feet. People get easily lost in upper skyline during winter, usually at the 7,400 ft level. If you are at that elevation on the route, look and try to locate a 100ft rock that spikes towards the sky, named "Coffman's Crag." Once you locate the rock, climb up from the east side of the rock being parallel with it at all times. You will reach the end of Upper Skyline when the route suddenly flattens out and you find yourself in a valley. You should see some people there if its after 10pm.
Reaching the tram station: Once you have reached Long Valley, turn right and walk a little more than a quarter mile until you see the upper tram station of the Palm Springs Ariel Tramway. In summer, there should be a clearly marked trail. There is a restaurant in the station (but the food is expensive). Most people doing skyline are tired at this point and ride the tram back down the mountain (cost: $23.25). The tram normally opens at 9am and closes at 9pm. If you want to keep going, there's still much more (but easy) hiking to get to the summit. 
San Jacinto Peak trail: This is the final push of the trip. This last part is 5.5 miles long and gains just under 3,000 feet of elevation. Walk to Long Valley Ranger Station, which is a wooden cabin, and fill out a free dayhike permit. You will be fined if you skip this part. To get to the station, turn left (assuming you are facing the same direction you just came from), walk across a small footbridge, and you should see it. You should also see a sign that says "San Jacinto Peak 5.5 miles" and it is pretty straight forward from there. Just follow the clearly marked trail. In winter you will need ice tools and snowshoes. The snow will be up to 20 feet deep sometimes in places near the summit. After hiking 2 miles on the san Jacinto Peak trail, you will come to Round Valley, a campsite used by people planning on reaching the summit who want an early morning start. This is not to be confused with Little Round Valley, which is on the other side of the mountain. 3.5 miles after Round Valley you will be standing on top of the 2nd highest mountain in Southern California.
The Summit: From 10,834 feet, you can see a lot. The buildings from the city of Palm Springs you started out at will merely be little specks in the distance. To the north is Mt. San Gorgonio, the tallest mountain in Southern California. On most days, you will be able to see the beach, over 60 miles away from the mountain. Seemingly right below you and to the northeast, is the San Gorgonio wind farm, which brings electricity to Palm Springs.
Camping
Camping is allowed in designated areas. More information can be found here.
Weather
Mt. San Jacinto is a huge mountain, which can sometimes generate its own storms. Dont be surprised if it is sunny and hot in the morning and snowing in the afternoon. People often get caught in blizzards in the winter and afternoon thunderstorms in the summer. Heres what temperatures to expect on parts of skyline in different times of year in degrees Fahrenheit:
Summer: Lower Skyline: 80-115 degrees, Middle Skyline: 70- 105 degrees, Upper Skyline: 50- 85 degrees, Summit: 40- 75 degrees
Winter: Lower Skyline: 40-70 degrees, Middle Skyline: 25- 60 degrees, Upper Skyline: 0-50 degrees, Summit: -15- 25 degrees
November (considered by most as the best time to hike skyline)- Lower Skyline: 50 to 85 degrees, Middle Skyline: 35- 65 degrees, Upper Skyline: 25- 60 degrees, Summit: 5- 40 degrees
In Summer
Due to the surprising amount of people who have died on Skyline from heatstroke, most start at 3am to avoid the daytime heat. Already the temperature at 3am should be above 80 degrees, rising above 90 by sunrise. Watch out for snakes and scorpions. Average daytime temperatures are 115 degrees in the summer, but can climb over 120 degrees.
In Winter
To avoid frostbite in winter, when temperatures can suddenly drop to -20 degrees at the summit with 80mph winds, it is recommended you bring insulated gloves and waterproof hiking boots if the forecast calls for 35 degrees as a high for 8,000 feet, which means possible 0 degrees at the summit. Bring extra layers, even if it feels like you dont need them.
The Ten Essentials
Items very highly recommended you should bring if you are very unfamiliar with the route in winter:
  1. Map
  2. Compass
  3. Sunglasses and sunscreen
  4. Extra clothing
  5. Headlamp/flashlight
  6. First-aid supplies
  7. Firestarter
  8. Matches
  9. Knife
  10. Extra food 
Photography
The best time of day to get photos is between sunrise and 2.5 hours after sunrise and between sunset and 2.5 hours before sunset. For most people, it will be very difficult getting this time of day perfectly because the tram opens at 9am and best photographic locations are above 5,000 feet, where it takes hours to reach by hiking. It is recommended that you camp in Round Valley to get those shots. There is no best time of year to photograph for Mt. San Jacinto. Its different in its own way every season. In winter you get nice shots of snow coated trees with the barren desert below, in summer you get superb sunrises with excellent lighting on the trees.
Things to Photograph
The Desert Floor: Starting at 6,000 feet, you will start to get increasingly nice views of the desert below. Point your camera north for the best desert scenery.
City of Palm Springs: The best place to photograph this will be from Grubbs view at the upper station of the Palm Springs Ariel Tramway. You will see patterns of buildings and whole towns underneath your feet. At night, the light from all the buildings make it feel like you are on a plane.
Jeffery Pines: These are found within a mile of the summit. They are no ordinary pine trees. They are hundreds of years old and survive constant 50mph winds, which make them gnarled and twisted into odd shapes. The best lighting for these trees would be within an hour after sunrise or before sunset 
Rime Ice Trees: If you hike above 9,000 feet within 2 days after a storm has passed, you will see the trees weighed down with massive sheets of ice and snow. Sometimes there will be icicles up to 30 feet long. Try to photograph the tree and also show the desert below to bring out the contrast of the different locations. The best lighting for these rime ice trees is within 3 hours after sunrise or before sunset.
The Crowds and Best Time Of Year for hiking
In summer, late spring, and early fall, the San Jacinto Peak Trail will be very crowded from people riding the tram. There may be as much as 40 people on the summit at a time. In winter, there may be a lot of people near the tram station and children playing in the snow. If you go 2 miles on the San Jacinto Peak Trail, you will likely find yourself in a completely deserted area for miles. There may not be anyone on the summit for days at a time. Lighting resulting from the sun shining off snow is also more dramatic than summer. As for lower, middle, and upper Skyline, it is pretty much deserted all year round, with an average of 2 people a week on the route in winter. Most people prefer to hike skyline in November when the desert floor has cooled off and the winter blizzards haven't arrived yet.
Requirements to hike Skyline
It is highly recommended you meet the requirements below if you are planning this hike this route:
- You have done a dayhike out and back that gains at least 5,000 feet.
- You can run 1 mile in 6 minutes and 40 seconds or less.
- You can run/walk 15 miles on flat ground in 5 hours or less with at least a 15lb pack.
- (in winter) You have route finding skills with either a map and compass, or GPS device. With an ice axe and crampons, you know how to french step, self belay, and self arrest.
- (in summer) You can withstand a temperature of 110 degrees Fahrenheit in a T-shirt and shorts for at least 1 hour.
Maps and Photos
Skyline Route photos
Skyline Route Maps 
More Information 
Weather forecast for Palm Springs (the start of Skyline route)
Current Weather for the upper tram station (elevation 8, 516 feet, at the top of Upper Skyline)
5-day weather forecast for the upper tram station 
LIVE Long Valley Ranger Station webcam (elevation 8,200 feet, at the start of the San Jacinto peak trail)- If you see snow anywhere in the picture, the upper portions of Skyline are very likely to be covered with snow
Palm Springs Ariel Tramway official website