This is a fairly well maintained dirt road, which gets heavy 4WD and off-road use, especially on weekends. A loop ride can be made by going up Little Annie or the Midnight Mine Road and down Summer Road. This is very scenic with great views of the town of Aspen, Castle Creek Valley and surrounding Elk Mountains.
The paved road quickly becomes a steep unpaved four-wheel drive road. Stay on the main road as it cuts across the front of Aspen Mountain and then switchbacks up Pioneer Gulch, reaching the site of the now closed Gwynn's Restaurant and the top of chair lift 1A at approximately the 2 mile mark. The steep switchbacks continue until the road contours into the top of Spar Gulch and reaches Bonnie's Restaurant (open only in the winter). The road then passes under the gondola before it finally reaches the Sundeck Restaurant (open winter and summer) at the top of Aspen Mountain.
From the top, there are spectacular views in all directions. You can access Richmond Hill Road (which follows the ridge behind Aspen Mountain to Taylor Pass), or Little Annie and Midnight Mine Roads (which descend into the Castle Creek Valley).
Directions from Aspen: From downtown, proceed on Durant Avenue east to Original Street and turn south. Follow Original 1/8 mile, keep straight and continue on the paved road as it curves behind 777 Ute Avenue and through the Aspen Alps Condominiums.