Climbing Pinedrops Trail

This unmarked trail in the Phil’s Trail system provides a great workout for legs & lungs. Nothing technical, just a good, fun climb.

As mountain biking season kicks into full gear in Central Oregon, my friends and I have started tackling longer hills. A good climb can get the blood pumping, making you feel you’ve really earned that downhill joyride. Hills are a great way to build stamina — which is always one of my goals — so I try to embrace the pain.

Fortunately, I have several friends who are climbers and their enthusiasm helps to carry the day when I’m feeling unsure or unmotivated. Now that the snow has melted off of Pinedrops (a two-mile climb in the Phil’s Trail system), I’ve started adding it back into my repertoire. It’s a great little unmarked trail at the top of Ben’s. When Ben’s intersects Road 300, follow the road to the left and keep an eye out for a narrow trail heading uphill on your right.

The Pinedrops trail starts to climb gradually, luring you into thinking, “This will be a piece of cake.” It twists and turns, winding up and down through manzanita and pines, protected from wind and sun. A little over a mile in, the trail flattens a bit and passes through a lovely grove of Ponderosas — an area we call the Picnic Spot, because it’s easy to imagine a few picnic tables scattered throughout. I like to take a quick breather here, because it’s early in the season and the hardest part of the climb is ahead.

From here, the trail quickly climbs in a straight, steep segment that punishes legs that are already tired. This is the hardest part of the ride. The trail then turns, rambling up and down again before descending neatly through the woods. There is really nothing technical about this trail but it’s a great endurance builder for legs and lungs.

The trail intersects with a dirt road where a massive bench invites riders to catch their breath and share snacks with friends. You’ll be adjacent to the trail marker for Whoops, a popular route for returning to Road 300, or you can descend on Pinedrops.

Pinedrops makes for a fun downhill, with swoopy turning and rolling terrain. For more of a thrill, check out the man-made hills and banked turns of Whoops. Do take it easy on your first time out on Whoops — if you get going too fast you can launch yourself off trail.

When my friends suggest Pinedrops, I remind myself of the benefits of climbing and let their momentum help me get going. Now that I have a base level of fitness, I’m trying to include more challenging rides in my weekly routine. Fortunately, my local cycling club (the Bend Bellas) offers lots of ride options and plenty of great people who are fun to ride with. Together, we have a grand time while help to motivate one another to do more.