Update 7/22/13 by mtbgreg1:
The Phil's Area Trail System is the go-to trail system for mountain biking in Bend. Even the other trails in the region that aren't actually part of the Phil's Trail System feed into or connect to trails that feed into Phil's.
According to the locals, and for the purpose of our trail listings, the boundaries of the Phil's Area Trail System is a square comprised of Skyliners Road to the north, Highway 46 (Cascade Lakes Scenic Byway) to the south, Bend to the east, and the Storm King trail to the west.
This complex trail system offers a variety of different trails, but on average the trails are very buff, very flowy, with some great corners to rail. The trail tread is quite loose and sandy, and gets very dry, especially late in the season, leading to "moon dust" conditions. Here and there you'll find some rock gardens, skinnies, and sections of flow trail with big jumps and massive berms! All of the difficult sections do feature ride arounds, making this an extremely beginner-friendly area.
This route goes along a popular trail close to town and is ideal for mountain biking. A lot of the roads and trail names are unmarked so watch for the Bike Route signposts.
0.0 - Phil's Trailhead. Head west down the wide cinder road FS road 4606.
0.2 - Turn left onto a closed road (Phil's Trail).
0.3 - Bear left at the fork in the road/trail (Kent's Trail) staying on Phil's Trail.
0.8 - Turn right onto FS road 030 (white pumice road).
1.4 - At a pumice pit the trail continues off to the left side.
1.5 - Head straight at the next trail junction with KGB Trail
2.2 - The trail tops out and crosses FS road 4610.
2.8 - At the fork in the trail (Kent's Trail) bear left, staying on Phil's Trail.
2.9 - (For a shorter option look for Voodoo Trail on the right that will connect you back to Ben's Trail.)
3.9 - Upon reaching a red cinder road (FS road 300) turn right. (for a longer option continue up Phil's Trail and coming down Woops Trail. )
4.2 - Look for a trail on the right, take that trail and head down Ben's Trail.
The trail winds and crosses the FS road 900 several times.
5.7 - Fade Left at the junction with the Voodoo Trail.
6.3 - Where the trail crosses FS road 4610 go right and then immediately left, fade left again and just after a few woop de doos look for the start of Ben's Trail on the right.
7.3 - Turn right staying on Ben's Trail.
7.4 - Fade left staying on Ben's Trail (MTB Trail on right).
7.9 - Join Kent's Trail and head back to the trailhead by turning left.
8.3 - Head straight at the junction with Phil's Trail and return to the trailhead.
9.0 - Return to trailhead.