(WINTER) HOLD ON! If you don't have much high-elevation, winter climbing experience, be careful in your planning and take a partner. Even the "easy" 14ers (Quandary, Sherman, Grays & Torreys) can be deadly in winter.
From Interstate 70, take Exit 171 and follow U.S. 24. Drive almost 5 miles and turn right onto the Tigiwon road. The turn is just before U.S. 24 crosses the Eagle River and starts to switchback up the hillside. The Tigiwon road is dirt and cars can usually make it to the trailhead. Drive just over 8 miles to the trailhead. More information on the Tigiwon Road (#707) can be found on the US Forest Service Motorized Vehicle Use Map for the Holy Cross Ranger District.
Fill out a Wilderness Registration Card and hike up the Half Moon trail (Photo #1 and Photo #2) to reach Half Moon Pass after 1.5 miles - Photo #3 and Photo #4. Cross the pass and follow the trail as it gradually descends west - Photo #5 and Photo #6. Below 11,400', Mt. of the Holy Cross and the lower Cross Couloir route is visible to the southwest - Photo #7. Continue over the northwest shoulder of Notch Mountain and descend toward East Cross Creek - Photo #8 and Photo #9. From Half Moon Pass, you will lose about 1,000' of elevation to reach the creek. After a steep descent, reach the thick forest near East Cross Creek (approx. 10,700'). If you're camping in the area, please read the information sign (Photo #10) which has a map of defined camping spots on the north (right) side of the creek.
Just after you cross the creek (Photo #11) but no farther than the boulder seen in Photo #12, turn left and walk into some old, closed campsites. Continue a bit farther to reach a stream (Photo #13) which drains the small pond just off to your right (west). Cross the stream and locate a faint trail which heads southeast. Finding this trail makes it much easier to navigate the next mile of hiking. If you're climbing this route in spring when snow may be lingering below tree line, it may be difficult to follow the trail so study maps and have a plan in case you lose the trail. Follow the trail southeast then south as it weaves up through large boulders and steep terrain. Near 11,200', the trail turns southwest and climbs a rocky section (Photo #14) before zig zagging through more large boulders - Photo #15 and Photo #16. Near 11,600', leave the trees and enter an open area in upper East Cross Creek where the trail will likely run out - Photo #17.
Continue south along the creek and climb to the right to bypass the large rocks seen in Photo #17. At the top of the rocks, locate a narrow passage through boulders (Photo #18) and continue along the upper creek. Weave through willows, rocks and then a lot more rocks to reach higher ground below the outlet of Bowl of Tears - Photo #19 and Photo #20. Between 11,800' and 11,900', you're passing under the Cross Couloir but this route does not climb from the absolute bottom of the couloir because of cliffs near the bottom. Instead, the route swings south and ascends a portion of the east face before entering the couloir, near 13,000'.
Pass the outlet of Bowl of Tears and continue along west shore, below Holy Cross' east face. By now you've probably figured out that the approach to the Cross Couloir is quite tedious. Turn right and begin climbing the east face - Photo #21. Take the path of least resistance through some rock bands and continue west up the face - Photo #22 and Photo #23. Above 12,600', angle right (north) onto the tundra (Photo #24 and Photo #25) and continue above 12,900' to reach the entry of the Cross Couloir, just under 13,000' - Photo #26. As you enter the couloir (Photo #27 and Photo #28), the cliff section which you took so much time to bypass is not far below - Photo #29. Once you're in the couloir, the route is obvious - Photo #30. You'll immediately face a slope angle near 40 degrees but it eases slightly near 13,400' before increasing as you climb higher - Photo #31 and Photo #32. Enjoy a challenging finish as the slope angle exceeds 45 degrees, just below the top - Photo #33, Photo #34, Photo #35, and Photo #36. Turn right to gain the summit - Photo #37. Photo #38 is a head-on look at the couloir. Unless you're skiing or boarding the summit, it's best to descend via the standard, north ridge route.