2-Day Bikepacking Trip in Bend, Oregon: Phil’s Trail System to Tumalo Falls

The Map

Want the GPX version of the map or just more detail?  Click here.

Bend… The Final Frontier

Bend, Oregon is well-known as a mountain biker’s oasis. Its flowy, hard-packed, grainy singletrack allows riders to pack on the miles each day while still experiencing technical rock gardens, whoops, and other exciting terrain, all meticulously maintained by the Central Oregon Trail Alliance (COTA). Few places have such an established mountain bike culture.

I’ve been itching to get out into the snow again after my last snowy adventure at Waldo Lake a little over a month ago, and this past Sunday and Monday presented themselves as an ideal chance for me to get out for a quick 2-day ride. Looking around at my various options, Bend’s ideal wintry conditions were calling to me, so I decided to brave the Santiam Pass in my Toyota Echo and drive down to the famous Phil’s Trail System, where I’d begin my little adventure.

Christmas Present = New roof rack!

Leaving the comforts of smooth Salem tarmac…

For the snowy mess of the Santiam Pass and Bend.

Starting at Phil’s Trailhead.

Beginning on Ben’s Trail, I rode about 3 miles before the well-trodden hard-packed snow gave way to fluffy powder that was simply unrideable. Noticing that a forest road was not far from where I was, I decided to posthole my way towards the direction of said road. While I normally would not condone such behavior, it worked out great for me. After working my way over to Skyliners Road, I had a very pleasant snowy ride up towards what I supposed to be the rest of my singletrack journey.

Ben’s Trail.

Skyliners Road.

The Krampus doesn’t make very good snow angels.

This was kind of a slap in the face.

Brief Intermission

Not being a Bend local, I was completely caught off guard by the lack of knowledge surrounding the topic of groomed trails in the area. After talking to the Bend/Fort Rock Ranger Station, as well as two different Bend bike shops, I was left lacking any new knowledge about my potential route. It turns out that hearsay from the locals is the best information around. Because of three separate interactions with local Bend residents, I was able to find the trails needed to get at least somewhat close to my destination; thank goodness my route had me pass through somewhat well-used trails.

Just Around the River Bend…

Having run out of road on Skyliners, I spent the next 1 ½ hours following my GPS to a road that didn’t exist through a No Trespassing sign (maybe it does exist and is just covered in snow, I guess I’ll never know), and then riding circles in a labyrinth of Nordic trails, finally finding the hallowed ‘green gate’ that one of the local residents told me about.

This is just a suggestion. The cabins up at the top are actually quite nice!

I took my endless circles on these trails out of the map up top, but yeah… I was on these for a while.


I knew that shortly I’d have a choice to make: turn right on the South Fork Trail and follow Tumalo Creek towards Tumalo Falls, where after about 3 miles I’d find a small shelter stocked with firewood and a place to keep my tent out of the wind; or, turn left on Tumalo Ridge Trail where I’d follow switchbacks up a ridge and after about 4 miles find a small shelter similarly stocked.

My two options.

I’ll never know if I would have made it turning left, but the shorter distance of the South Fork Trail appealed to me as day was fighting a losing battle with night. Unfortunately, after riding 2.3 miles my trail fork towards the blessed shelter was in fact nonexistent, and after retracing my steps to be double sure it wasn’t there, I realized that the hoped for fire and shelter simply weren’t going to be a part of this trip. Maybe next time.

Tumalo Creek.

Losing the last of the light.

The last couple miles were covered via headlamp light.

Even though I didn’t have a shelter, my campsite was pretty awesome.

Dinner, an audiobook, and scotch finished the night off right.

The Woods are Lovely, Dark, and Deep, But I Have Promises to Keep

Sleep eluded me for much of the night because my feet were painfully cold. Eventually at 3am, I got up, boiled some water, and stuck my now hot Nalgene into the bottom of my sleeping bag, while also taking off my socks. This seemed to do the trick, and the next 3 hours went by relatively quickly.

It was either boil water for my feet or head out at 3am… I’m glad I opted for this option.

As always, by some stroke of weird bikepacking voodoo, I felt chipper and ready to tackle the rest of my ride when I got up in the morning. I technically had food for one more overnighter in case I found the trails to be stellar, but since my dad’s hip replacement was scheduled for the following day and the trails were just plain confounding, I decided to make my way towards the car rather than further explore the mystery trails.

A bit of morning snow buildup on the Krampus.

Tumalo Falls in the morning.

Ready for the ride back.

I did do a bit of exploring up the North Fork Trail before making my way back down to Skyliners Road and Phil’s Trail System, but this detour proved to be disappointing, as it was not the hard-packed snow needed for riding.

Once back at Phil’s Trailhead, I finished the ride with a small 4 mile loop before heading home. While short, this ride was just what I needed to satiate my bikepacking appetite for the next few weeks.  I often set strict mileage expectations for myself when heading for the outdoors, but this trip showed me the significance of simply getting out for the enjoyment of the experience instead of focusing on unimportant personal fitness goals.  The point is to have a memorable experience; mileage covered should simply be an afterthought.

Sun rising on my way out in the morning.

Three Creeks Brewery in Sisters. Great beer. Great burgers.


Categories: Oregon Bikepacking

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4 replies »

  1. Great post – what an adventure. I was a little nervous you being out there alone, kept me reading all the way through. I would’ve suffered all night, never thought of boiling water for cold feet. Can’t wait til your next story

    • Wow, thanks Frank. Glad it kept you interested. The cold feet are an ongoing battle for me, so I have to have tricks in my arsenal to combat them. At 3am, it was either figure out a way to warm them up or pack up early and head for the car. I’m glad I stuck it out.

  2. What an adventure. I’ve done some of those trails in the summer, can’t imagine trying them in deep snow. I’ve also seen those cabins, not sure I could get there without a guide, but it would be a fun adventure. Try talking to the folks at Cog Wild- very nice folk, and I’m sure they would be glad to give you trail info.

    • Great advice Jack, thanks. I’d like to do a 3 day trip that starts in Sisters and works its way around Bachelor in the summer, using many of the same trails, so I’ll make sure to give them a call before heading out.

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