Phil's Trail system is by far the most popular trail in Central Oregon. It is close enough to ride from town and it was built by bikers for bikers. There are occasional runners in the first mile or two but there is plenty of room for bikers and runners to pass. Except for a few technical sections most notably on C.O.D. and lower Grand Slam, most of the riding is fast singletrack. For the first five miles or so, the riding is gradual and suitable for beginners or riders not in the best biking condition. Where the climbing does get a bit steeper, like past the Road #300 on Ben's and Phil's, less experienced riders will likely be ready to turn around anyway. There are dozens of variations on routes that can be made out of the various trails especially if you use the logging roads to connect them. This helps locals from getting bored on the same old loop. For those in good shape, these trails can be continuously linked to the higher elevation trails long enough to tire just about anyone. No matter where you are, if you are not tired enough there is no doubt some loop you could add. The truly great thing about most of the riding on Phil's is that the descents do not require a lot of constant breaking and you can let em run, not to mention that many of the ascents are gradual enough that you can actually have fun cornering going uphill.
The maize of trails can be challenging to newcomers but most of the intersections are marked with numbers and names that are on just about any mountain biking trail map of the area. The printable map provided on this site also has intersection numbers. Also, if you are lost, you can generally ask directions from other riders who are usually not too hard to come by. In the last few years there have been many trails that used to have one name that now have many names, mostly personal names. For some reason it has been deemed necessary lately that every little segment have it's own name. Consequently you will see names in magic marker on intersection posts that do not necessarily agree with maps or even the names on the posts made by the Forest Service. This could possibly be a source of confusion. The intersection numbers should be consistent with the maps.
This is not a particularly scenic trail system. It is almost all forested and there are scant few viewpoints. This was one of the first areas to be completely nuked by early loggers so most of the ride is in second growth ponderosa pine. It has been so long since then, that it is starting to look like a forest again. However, on November 1st, 2007, a big thinning operation started, covering a major portion of the Phil's trail system. This thinning effort is getting a big shot in the arm as of 2011 and will go all the way up to Swampy Lakes. Ultimately, this will be a good thing, and it needs to be done, but it will look like a bad haircut for a few years in places. There are other rides in the Bend area that are more scenic if that is what you're after. Phil's is more for blasting around and racing your friends where you are not too focused on the scenery. If you want to meet other riders, the trailhead at Phil's is the place.
Although you probably won't do any jail time for riding directly up the Whoops Trail, this is not advisable. One of the reasons is that downhill riders are supposed to give the uphill riders the right of way. This means slowing down or stopping to get out of the way for uphill riders which is going to screw up a hard earned descent. COTA now has a large sturdy sign now on the one way nature of the trail at the bottom.The only problem is that there is not much signage to direct you up the road. It starts just to the right of the bottom of the trail as you look up at it. There is one junction about a hundred yards up where you bear left. Eventually if they do not come up with a new route the road will become overgrown and will become single track. Unfortunately this road instead of becoming single track is being heavily used by shuttle riders.The other option is to take Phil’s (or whoever's first name that trail is now) up to the helipad. Even if you take the helipad route up do not be surprised to see yahoos in vehicles at the top. They really need to shut that road down and or at least create an uphill single track trail. The road now has deep powderized dirt from the aggressive vehicle traffic. There are too many trails in town that can be easily run as shuttles and those trails get chewed up much faster. There need to be some trails left that you have to earn your way in there to enjoy them and be able to get away from cars and car culture.
Trail Fee: Although this trailhead is in the National Forest you do not need a forest pass and there is no fee.
Getting to the Trailhead: From Google Maps copy and paste "NF-4606 @44.043520, -121.385600" as a destination. If you pass the parking lot with all the cars with bike racks, and people getting ready to ride you have gone too far.Phil's Trail System 8.5 x 11 Pocket Map (Marvin's, Funner and Tiddly Winks added 5/29/2010)