Milestone Mountain (4158m), the most prominent (but not highest) mountain of the
Great Western Divide, is located as far from a trailhead as you can go.
If you approach it from the west (Roads End in Cedar Grove) the one-way
hike is about 42 kms.
If you approach it from the east (Symmes Creek trailhead in Independence) the
hike is about 40 kms.
The difference is that you have more trail on the western side, and the
final pinnacle (that one can see from Mt Whitney to Alta Peak) is feasible
only on the western side.
Also, the eastern approach involves hiking up Shepherd Pass or from Whitney
Portal: Shepherd Pass is a logistical nightmare, and anything near Whitney
is a bureaucratic nightmare. The western approach from Roads End is relatively
Midway (4165m) is a few meters higher than Milestone but a lot less famous. It is also a much easier climb (class 2 instead of class 3). Being next door, the route is identical except for the last part.
Eastern routeClick here for the trail to Shepherd Pass. Once you reach Shepherd Pass, continue straight on the trail until you hit the John Muir trail. Turn right (north) for one km on the JMT. Turn left onto the first eastern trail and continue straight east (you'll pass the junction with the Lake South America trail). This trail hits a north-south trail at the Kern River. At this junction there's a little lake. Go south for about 400m and you will see the Milestone Creek coming down from the Great Western Divide. If you are lucky, you will not need to find the Milestone Creek but you will find a use trail that climbs the wall on your right. At this point leave the trail and start hiking upstream trying to stay to the right of the northern-most branch. After some steep climbing, you reach a first plateau/meadow. That's where you will probably lose the use trail. The Milestone Creek on your left is now very wide and appears to create one lake after the other (not on my map). Continue up this drainage and you'll start seeing the shape of Milestone Mountain. The mountain to the right is Midway Mountain (4165m), the highest peak in the Great Western Divide. Follow the creek upstream when it bends to the north. Be sure to turn left/west again and not follow the tributary that comes down from behind Midway (presumably from Table Mountain). Now the creek is minimal and you are probably walking between moraines and snow fields. The route should be obvious though: aim for the saddle between Midway Mt and Milestone Mt. From the saddle the route to the pinnacle of Milestone is not obvious but the direction is, so you will eventually find a way to get on the first western chute that comes down from the pinnacle. A more difficult alternative is (way before the saddle) to climb the moraine towards the pinnacle and then climb the notch just north of the pinnacle (class 3) which takes you straight to the pinnacle. Once at the base of the pinnacle (you are on the northwestern side of it), there is a cairn that marks the first step to climb the pinnacle. The first step is the most difficult. Once you've done that, there are at least two easy (if breathtaking) ways to reach the summit. I found very easy class 2-3 on the southern side (alas, with colossal exposure) but the cairns showed a safer if slightly steeper way with no exposure.
If you are heading for Midway, the easiest way is to climb the very prominent eastern ridge from down below the drainage. The northern side of this ridge is very easy class-2. A more difficult way it to climb to the Milestone-Midway saddle and then climb the class-3 southern ridge.
Milestone Mt from Junction Peak:
Panorama from Mt Keith:
Panorama from Shepherd Pass (Milestone Peak is at the far right):
The eastern cross-country route to Midway and Milestone Mt
Milestone Mt and Midway Mt from Mt Williamson (eastern route)
Western routeTake Highway 180 from Fresno all the way to the end, past Cedar Grove to Roads End. (You can camp for free in the portion of the paved road that falls into national forest). Hike on the Bubbs Creek trail to the junction with the Avalanche Pass trail (Sphinx Camp), then turn right over the bridge to the very steep Avalanche Pass trail (that follows the Sphinx Creek rapids). See this page for detailed directions (but continue to Avalanche Pass instead of leaving the trail for the Sphinx Lakes).
Basically, from Sphinx camp very steep switchbacks take you to the crossing of the Sphinx Creek and then more switchbacks take you to Avalanche Pass. The elevation gain in these first four hours is about 1,500 meters. The trail then descends rapidly towards a ranger station located at Scaffold Meadows. You can bypass it and save quite a bit of time if you keep heading south (or, better, southeast) when the trail bends west after contouring a small peak. After crossing a creek, climbing a ridge and then climbing a second (much smaller) ridge, you emerge on top of the the bank of the Roaring River: the trail is just north of that river (down below your ridge). Depending where you are on the ridge, it might be confusing which is the Cloud Canyon. Just head down the ridge as southeast as possible and you'll hit the trail, which will solve all doubts.
If you don't take the shortcut, you reach a four-way junction (26 kms after the start): take the Colby Pass trail into Cloud Canyon. After crossing the small creek that comes down from Mt Brewer (from the east), the Roaring River bends south and carves the Cloud Canyon. The trail coasts the river all the way through a forest to some increasingly large meadows. At the end of the meadows the trail climbs steeply the wall to the southeast (not what looked like the obvious canyon to the south) to reach Colby Lake (3226m), about 15kms later. Follow the eastern creek upstream in the general direction north (don't take any of the southern tributaries) and you will get to a lake (3502m) that lies just below the western face of Milestone Mt and the western ridge of Midway Mt.
For Milestone Mt you have to coast the lake to the north side and then start climbing east. Note that you never see the real summit as you are coming from the west: what you think is the summit is actually a false summit but it is a good reference point. Head for the S-shaped chute that becomes very visible once you are on the northeastern side of the lake.
The climb is easy class-3. When you reach the false summit, turn left around/above it and ascend to the crest. Once on the crest, the summit pinnacle is very visible: scramble east towards its base. See the eastern approach for how to climb the pinnacle.
For Midway Mt you have to coast the lake to the north side and head east for a ramp that allows you to walk west above the cliffs. Once above the cliffs, you reach an area that is almost flat from which you can climb the class-2 ridge to the top.
(Click on the names to see the topomap)
The two routes, western and eastern:
From the topomap, it seems also possible to reach Roaring River station by hiking cross-country from the Moraine campground located before Roads End, coasting Sentinel Dome but it implies wading Sugarload Creek in Sugarloaf Valley.
An alternative to the Roads End trailhead (with less elevation gain/loss) is the Marvin Pass trailhead. Whether you are coming from the north (highway 180) or south (highway 198), turn east into Big Meadows Horse Corral Road (10kms south of the Big Stump entrance to Sequoia/Kings Canyon parks), also known as forest service road 14S11. Continue on the paved road ignoring all side roads. You will pass two gates (the road is closed in winter). When you reach the sign "Marvin Pass trailhead", the road makes a sharp right turn and gets tough for the last 4 kms to the parking lot, which is also the Sequoia High Sierra Camp parking lot (GPS 36.741, -118.738). Hike to Marvin Pass (3 kms) and descend the other side. About 1 km after crossing the Rowell creek (and 5 kms from the trailhead), you should reach a junction (mostly obliterated in 2013): if you see it, go left and then left again to the Sugarloaf trail, but most likely you won't see any junction at all. Then you head east towards Comanche Meadows (5kms, 10 from the trailhead), where a trail joins from the south (Belle Canyon trail). Continue straight east. From Comanche Meadows to the Roaring River Ranger Station is about 13-16 kms (depending whether you trust a modern GPS in kms or the ancient signs in imperial miles). So the total from the Marvin Pass trailhead to the Roaring River station should be about 23 kms.