Scramble up the ledges to the right of Midway, to below the big roof.  Traverse left below the roof on good edges, and then upward through blocks and cracks to a good belay stance.  The second pitch climbs up and then traverses right into a crack system, and can be run all the way to the summit with a 60 meter rope.

Winter Solstice

From the Leavenworth guide book:

"Just right of the Midway chimney, this route connects a trio of bolts leading to a clean crack crux."

This route starts on the same belay ledge as Midway, just over to the right about 10-15 feet. There are three bolts slanting up and to the right that help protects some slope-y, slabby, face. After passing the three bolts, you'll get to the beginning of a clean, finger/thin hand crack. This protects very well and getting into and over the bulge at the bottom of the crack is the crux. After a 3-4 move sequence, you'll hit a bomber, incut jug in the crack and the route eases up.

Definitely worth doing if you're in the area. I'd almost give it three stars, but the climbing down low is mostly uninteresting.

Equinox

A very nice 3 pitch 5.8

The crux is getting up the first 20' and mid way up the 2nd pitch passing an old bolt/aluminum hanger on face moves.

When you get through the hard part of the 1st pitch, trend left till reaching a tree on a big ledge, a bolted anchor there.

The route veers up and right into a groove like inside corner or open book , pass 2 good pitons and the old bolt with aluminum angle for hanger. Veer right on a finger traverse ,pass another old piton and gain the arrete, either belay here or further up on horizontal cracks. Comes out on the north (left) side of the summit block.

I have led out from the bolted anchor all the way to the summit block in one pitch, even with scant gear and long slings pretty bad rope drag.

One should be a expert moss leader on this.

Saints

The first pitch is thought provoking tricky climbing. Not a great first 5.8 lead.

This could be done in 2 or 3 pitches and you could avoid most of the upper Saber pitch by climbing further right.

Century

Canary ascends from the right side of Logger's Ledge and reaches the top of Castle Rock in 2 pitches (3 may be necessary with a 50m rope).  A memorable line, Canary combines interesting climbing with terrific exposure.

Approximately 100 feet to the left of Saber, a short section of face climbing leads to a right facing dihedral and a broken crack system that reaches the left side of Saber ledge.  This is the start of Canary.

P1.  Begin by climbing approximately 15 feet of unprotected face to the base of a right facing dihedral.  This section is not trivial, but the holds are positive and it is no harder than 5.7.  Alternatively, it may be possible to begin in a small dihedral to the left and traverse right to gain the crack system at the top of the face.  From the top of the face, follow the dihedral and subsequent crack systems up with good gear.  Ascend until you are under the giant roof, then break right onto Saber ledge at the top of the crack system.  This pitch is the technical crux of the climb, culminating in the moves up and onto Saber Ledge (5.8).  Belay from gear or the giant eyebolts on the right of Saber Ledge.

P2.  From Saber ledge, contemplate what lies ahead.  The second pitch begins with instant exposure, and the airy step off Saber ledge may be the pyschological crux of the climb.  Begin by traversing obvious holds leading left and slightly up from Saber ledge.  Though intimidating, the traverse is easier than it looks, and giant holds await you on the arete.  It is possible to protect the traverse with a reasonable small alien on the face, otherwise it may be possible to place large gear (with long slings!) above Saber ledge before beginning.  Upon reaching the arete, climb past two bolts and follow your nose and your gear on increasingly easier climbing to the top of the formation.  Like many routes on upper Castle, the exact line is not obvious; expect some runouts on easier terrain. We were able to reach the summit with a 60m rope; a 50m would be somewhat short.

To descend, follow the trail off the back of the summit to Logger's Ledge.

Canary

First climbed in 1950, Saber begins from the far right side of Loggers ledge and reaches the top of Castle rock in 2 pitches.  Look for a left angling ramp just to the right of a large, low roof.  This is the start of Saber.

P1.  Climb the left angling ramp to the base of a left facing dihedral.  The rock in the dihedral has been polished to a slippery, disconcerting, mirror-like sheen.  When you hit a diaganol crack heading up to the left follow it to Saber ledge.  Belay from bolts. (~90 feet)

P2.  A few easy moves (~5.5) on the left side of a wide chimney take you up onto emminently forgettable and blocky terrain.  The climbing gets easier as you ascend, and I found myself on 4th or 3rd class terrain long before reaching the top of Castle rock (~190 feet).

I've stuck with the historical rating for this climb, which may be a bit of a sandbag-- a more realistic rating for the first pitch may be 5.6.  Combined with the polished rock, this route is probably not the best choice for a fledgling trad leader.  One star for history and for being an accesible moderate as well as a good place to booty gear, but I can't imagine wanting to do this twice.

Saber

Start as for MF Overhang, but continue to trend left after the first crux, ultimately pulling the large bulge/roof above the face of No Such Thing as a Free Lunge.

MF Direct

This route is listed as 10b, I think it is more like 10++, harder then Brass Balls- which for me is more like Crack of Doom- 10a.

Not often climbed, but worth doing.

There are 5 routes that go through the same roof.

From the left is Body and soul which still has 2 pins at the roof and  is thin,

and then Devil's Fright, which is more of wide fingers to  tight hands crack at the roof move.

Devil's Fright

Perhaps the "hardest" route at Castle Rock, Rainshadow Direct had gone though a complex history to become the classic sport climb that it is today.

Originally a 2-pitch A3 aid climb put up by Fred Beckey, Eric Bjornstad, and Jim Stuart, it was freed during the great Ltown renaissace of the mid-80's by Gred Child, Matt Kerns, and Jim Yoder. Former PNW crusher Kyle O'Meara envisioned a direct start up beautiful white rock which would allow the route to be climbed in one pitch. Unfortunatly, Kyle ran out of bolts, and was only able to sink in the first three. Nonetheless it didnt keep Kyle from freeing the line with a stick clip to start and traditional pro (a few cams and a sea of manky fixed pins) through the upper crux bulge. This half-finished pseudo-"traditional" version saw possibly just one additional free ascent over the next few years. In the spring of 2014, Dave Morales, added the missing couple of bolts to the direct start, replaced the manky fixed pins through the upper crux with bolts, and added a lower 2-bolt anchor.

The route begins with beautiful climbing using perfect edges and side-pulls on aesthetic white stone. From a midway rest ledge a perplexing bouldery crux leads to a more moderate finish up a shallow corner system.

Rainshadow Direct

A great climb up a widening crack.  Begin with a hand size crack that widens to offwidth and then to chimney.  The crux comes in the first 30ft but runnouts in the chimney keep things interesting.  Top out on Jello tower.

Damnation Crack

Slim Pickins climbs just right of MF Overhang.  If anything it's one of the more visually pleasing pitches.

Slim Pickins

The only sport route at Castle Rock (thanks to a couple of choppings), and a good one.  Some bouldery moves off the deck put you square up with a power crux at the third bolt.  There are cool moves the rest of the way; mostly sustained gently overhanging edges, with a deadpoint move to a rail and...well, I won't say anything about the end.

Das Musak

Worthwhile and historic option for the adventurous, which climbs the face left of the Saber corner, linking discontinuous cracks. Belay at Saber ledge at the bolted rap anchor. An optional second pitch angles right then up to the summit on typically vague upper Castle terrain. Depending on rope length, you may need a short third pitch to summit.

Directissima

Another variation of Saints. Follow horizontals and flakes up and left to a corner filled with poop and detached blocks. Finish as for saints either left to the rainbow connection anchor, or right to Angel anchor.

I started scrubbing a finish that avoids the junky corner by cutting right on good holds under a small roof. When you are just below the junky corner, cut hard right.

By the Sea

Climb the pod that makes up the start on Saints. Instead of exiting left out of the pod, traverse right and up through a few bulges on underclings jugs and flakes. Finish at the Angel Anchor.

Short N' Sassy

P1 (5.6): Climb the chimney on the right side of Jello Tower to the bolted anchor at the top of the tower.

P2 (5.6): Step across the gap and head up the right facing corner passing a large roof on the left. Make a slabby traverse right (crux) at some point to a wide/gully crack. Gear belay at a good little pocket ledge.

P3 (5.2): Head up connecting whatever flakes and knobby slabs you like; generally head up and right past the huge hueco up a big flake and then climb the easy slab all the way to the summit.

Midway

The direct start to Saber begins in the right leaning crack to the left of the standard start. A bouldery move off the deck leads to balancey climbing following the crack to the polished corner. Head to Saber Ledge and finish as per the rest of the route.

Saber Direct

A weird move onto a ramp leads to cracks leading to Saber Ledge. The second pitch leads up and right.

Cat Burglar

This is the steep face left of the Midway chimney.  Climb steep terrain to a bulge midway up the face.  After pulling through the bulge, the difficulties ease.  The climbing and the gear are both better than they look from the ground.  Belay from bolts on top of Jello Tower (shared by all Jello Tower routes).  Consistently fun and interesting 5.8+ moves the whole way.

South Face, Jello Tower

Old Gray Mare

There are several variations I have done off the Saber ledge. This is described as a horizontal traverse after going up the Saber Chimney  to join Canary after the bolted section. The book does not describe where or how far up Saber the horizontal is, maybe about 30' I have traversed a steep wall and come out on the blocky arete right of Canary.

Another good variation is to go straight up the face between Canary and Saber from the Saber ledge. It is still 5.9, but has some tricky steep face climbing and watch out for fragile flakes, instead of joining Canary, keep going up blocky arete, veering more right and come to a bolted anchor on the face left of Saber inside corner.

Orange Peel

Climb straight up the dihedral, after the step across, then move left on to exposed face. From a ledge, several variations, to the top are possible.

Midway Direct

This climbs the outside, left arete of Jello Tower.

MF Overhang

DDD follows insipient cracks and small edges up the face to the left of Damnation Crack.  There is pro but it can be thin and difficult to fish in while on the tiny edges.  This route should only be led by those confident at the grade.

The route, originally put with 3 bolts one of which was also used as a belay.  The original and additional bolts have appeared and disappeared several times over the years and the route remains a contentious poster child of bolting wars.

Most climbers now climb the route as a TR accessible from any of the routes that top out on the Jello Tower.

Dan's Dreadful Direct (aka DDD)

This thin corner crack offers mediocre gear, uninspiring feet, and plenty of sand, moss, etc.  If you like scaring yourself on dirty, poorly protected, short lines, then Lucky Charms is for you.

Begins in the right-facing dihedral uphill and to climber's left of OGM, and follows the dirty finger crack upward, trending eventually rightward to finish at the ledge below Crack of Doom.

Lucky Charms

Just to the right of the bolted line of Das Musak lays a gear route that rarely sees an ascent. Step off the boulder and clip the first bolt to protect a ground fall, a few hard moves leads to a jug and a perfect 0.5. Continue up and trend right to pull the first roof, a few more cruxes remain.

If it feels hard for the grade you are probably right, felt more like 11c then 11b in my book.  May look a little dirty, but it is clean where it counts.

Possible to reach the top anchor from either Saints or the top of Das Musak.

Rainbow Connection

The crack climbs an interesting line up a wide crack and through a roof.  The crux moves are physical but short lived.  Once past the roof move right and link up with Canary.

Crack of Doom

This pitch climbs the white colored rock climber's left of Crack of Doom. The crux is in that white rock, as it is slick and quite polished on flaring not-so-fun jams.

Devil's Delight

This steep classic has been challenging climbers for decades.  Solid rock and the unique features of the Jello Tower combine to make a stout climb.  The pro is good but you'll struggle to get it as you forearms pump up.  A combination of crack and face moves lead to the top of the tower.

The Nose, of Jello Tower

Start is the same as Cat Burglar with the boulder move up onto the ramp. Take the crack leading into a thin seam under the roof on the face. Crux is pulling the roof. After a few pumpy moves the climbing gets easy and dirty from there up to Saber ledge

Hangdog

The start to this route is an ultra-classic, super-short finger-crack. There's a good rest at the handjam pods high on the route. Some consider it cheating to reach out to the rail at any point that is not the very top of the horn. Also, watch out on warm days as the crack and the super-polished footholds can get very greasy. The route continues up to a rap anchor and several more pitches to the top of Castle Rock, but this is rarely climbed.

Angel

No Such Thing as a Free Lunge is an athletic route up the glass smooth north side of Jello Tower on Upper Castle Rock.  The climbing is sustained and the gear finicky.

Description

Location

Protection

Routes in Upper Castle