Bikepacking The Oregon Outback: Sept, 2023

The Oregon Outback bikepacking route is a 364 mile mixed terrain trail that begins at the southern tip of Oregon (Klamath Falls) and ends at the northern tip (where the Deschutes and Columbia River Gorge meet). My dad floated the idea of doing this ride months ago - after lots of back and forth, we decided to go for it. My friend Nick and his dad, Bob, decided to join the party as well.

Before we get into the ride, I need to give a special shout out to my partner Anne. We have two little kiddos, so when one of us leaves for a while, it makes life much harder for the other one taking care of the kids. I did quite a bit of traveling this year (a few work trips + this ride), and she’s been incredibly supportive during each trip. It’s no small feat juggling the kids solo + she’s simultaneously working super hard to grow her new plant gifting business, Hey There, Houseplant, so I was very thankful we figured out a way to make this trip work. Anne rules. I am a very lucky dude.

Day 1: Drive to Klamath Falls + Trail Camping

We left Benicia at around 9am and headed north for Klamath Falls. The excitement was high as we hit the 5.

We stopped at a gas station for some snacks and water. On our way out, we spotted this Butts On Things sticker machine. Of course, we had to snag one for Nick’s ongoing sticker collection. He scored big.

Through mutual family friends, we found a place where we could safely store my dad’s truck while we were away. The plan was for us to rent a truck in The Dalles once we were finished with the ride, then drive back to Klamath Falls to pick up my dad’s truck before driving back home. It was incredibly nice of Doug & Lorna to let us keep our truck at their place. They even sent us off with snacks and beers! THANK YOU DOUG & LORNA!

Luckily, Doug & Lorna live right down the street from the beginning of the trail. After loading up our bikes, we said our goodbyes and started pedaling. We wanted to get a few miles in before setting up camp that night.

The Riders

This is my dad, David. Not sure who I’d be without this guy (and my mom of course). My dad got me into bikes, and I’m so thankful for that. He’s always there when I have bike questions (or any questions!) + he usually has the parts I need just laying around in his garage. I lucked out when it came to parents!

This is my friend, Nick. This guy is good at lots of things, including riding bikes. Nick grew up in the town over from me, and we eventually played in bands together, then later lived in SF together. He’s probably one of the funniest people I know. He also inspired me to get a Riv!

This is Nick’s dad, Bob. Bob grew up in Livermore, CA, but now he lives in San Marcos, TX. He’s a truck driver, a country music lover, and a solid dude to share the trail with.

It was starting to get dark, so we began looking for a place to camp. The part of the trail we were on was flat & quiet, so we decided to camp right on the trail. It was here where my dad realized that he forgot his tent! While he was packing his stuff, he decided he didn’t want to bring the rain fly, so he removed what he thought was the rain fly, but it was actually his tent that he took out. Whoopsies! Time for some cowboy campin’.

Day 2: Sprague River + A Magical Campsite

After coffee and a quick breakfast, we packed up our things and started riding.

We eventually made it to the small town of Sprague River, where we restocked on water and snacks. There were definitely some characters coming in and out of the convenience store we were resting at. One woman rolled up on a 250cc enduro wearing sneakers and pajama pants.

“Where did you ride from,” my dad asked.

“Panama,” she said.

My dad just about spit out his gatorade and proceeded to ask her a million other questions. In the 20 or so minutes we were there, we probably saw enough to inspire a novel. It was amazing.

One thing everyone talks about during this first stretch of the ride are THE GATES. There are LOTS OF THEM.

At first, these gates were kinda fun - a good excuse to get out of the saddle and regroup. But after a while, it started to feel like they’d never end. I didn’t count the gates, but there must have been 30+ of these things.

Another fun part of this stretch is watching the cows. At one point we were essentially riding with them on the trail. They had a playful energy and it seemed like they enjoyed having us there.

In addition to the cows and gates, there were lots of other obstacles on the trail we had to pay attention to. Sometimes the trail was so overgrown that it didn’t even look like a trail at all. We had to choose our lines carefully - it was hard to take in the scenery sometimes because I was too focused on not bailing, which I almost did many times.

We finally made it to the section of the day’s ride where we read about multiple bush camping options, so we kept our eyes peeled. We came across another trail that veered left and made its way along the Fivemile Creek, so we pulled over to check it out. At first, it seemed like the perfect spot, but Nick decided to walk down the trail just a bit further to see what was there. I’m really glad he did, because he stumbled upon one of the best camping spots I’ve ever seen. It was right next to the creek with beautiful flat grass patches + a makeshift fire pit. It was glorious. We set up camp and started cooking some dehydrated meals for dinner - fettuccini alfredo with chicken for me - which actually tasted amazing.

While we were eating, two more cyclists showed up across the creek - Hannah & Meryn (from Vancouver, BC) - who were doing the same ride. There was tons of room on our side of the creek for camping, so we told them how to get across. We chatted about our bikes + how the trip was going so far before calling it a night. We would end up riding with Hannah & Meryn off and on throughout the rest of the trip.

Day 3: Silver Lake + Meeting Brandon & Nova

Everyone slept pretty well at the magical creekside camp site, so we were feeling good about getting back on the bikes. Hannah & Meryn were ready before us, so they started riding while we finished packing our bikes.

We were all pretty sore at this point, but we could feel our legs getting used to 8+ hour days of riding. After reaching a rest stop, the trail ended and we started riding on pavement, which was a welcomed change. We were jammin’ at a solid pace while enjoying some great descents.

The pavement eventually ended and we were back in the dirt, which was starting to change a little bit - now it was an awesome red / amber color. We started to get a preview of some harsh washboard trails - where every line you took was nonstop rattling from bumps and ruts. It was pretty miserable at times.

We kept on riding and made it past the Cowboy Dinner Tree - a restaurant in Silver Lake popular with cyclists doing this route. We were originally going to eat here, but the only reservations we could get didn’t line up with our arrival date. In a way, I’m kinda glad we skipped it because when we pulled into town, we were greeted by a friendly guy named Brandon and his Alaskan Malamute, Nova, who were taking a break at the Silver Lake Mercantile store. It turns out, Brandon lives in Oakland and was doing the ride on an electric assist cargo bike - he was carrying a trailer with extra batteries & supplies + he had a big front bucket for Nova to sit in. We were all pretty blown away over his rig!

Brandon and Nova took off and headed for Fort Rock, which was about 20 miles away, while I sipped on a Modelo tall can with this guy…

Another highlight of Silver Lake was chatting with the store owner, Dave. He was incredibly friendly and let us hang out front for as long as we wanted. He even offered to let us camp in his front yard, which was right behind the store. I was struck by how accommodating and friendly he was to a bunch of random strangers. Dave also runs the motel right next to the store, and after my dad heard there were rooms available, he was stoked to stay there, so we all ended up staying there that night. Dad and I had Spaghettios + a few more brews for dinner.

Day 4: The Red Sauce

We woke up feeling rested after a night in the motel and made coffee at the picnic tables out front.

Today was going to be one of our hardest days on the trip. The stretch from Fort Rock to the Prineville Reservoir is a 70 mile haul with very limited water, so we’d have to be careful about how much we drank. Bikepacking.com does a good job warning you about this part…

I had 3 water bottles + a 2 liter bladder that I carried in my handlebar bag. I was hoping that would be enough.

We made it to Fort Rock and met up with Brandon and Nova again, who ended up camping behind the bar in town. They were still packing up, so we made our way to a restaurant in town and got a late breakfast / early lunch. The Fort Rock Restuarant and Pub is a must if you go on this ride. Incredible food + everyone was super friendly.

After we finished up our meals, we filled up our water bottles and ventured onward. This is where things start to get hairy…

This part of the ride is pretty tough. After the pavement ended, the trail got super bumpy (we kept yelling “AHHHH” “NOOOOOO” “WHYYYYYYY” due to the constant washboard feel). The miles were slow and it was pretty grueling. Once we got deeper into the forest, the dirt started to change to a deep red. This was the “red sauce” we had heard so much about. Parts of the trail were soft and we almost washed out many times. Another fun fact about this stretch - yellow jackets like to hang out here. Every time we would stop for a rest, the yellow jackets would appear almost instantly. They didn’t bother you too much if you were moving thankfully, so we only stopped briefly here. I didn’t take that many pictures during this stretch of the ride…probably because the trail was absolutely kicking my ass.

Bob’s pace was a bit slower than the rest of us, so we ended up pulling ahead quite a bit. He told us to go on ahead and ride at our pace. We made it to the end of the red sauce and found ourselves at Highway 20. We accidentally rode right past our bush camp option and got a text from Bob that said he was going to stop there for the day. We found ourselves in a bit of a pickle….the next real campsite was about 20 miles away. We were running out of water + we were getting pretty tired. We decided to push on though, and link up with Bob the next day.

The next 20 miles were a doozy. There was a massive climb that took us to the top of the reservoir - it completely wiped me out. Once we made it to the top, there was an awesome descent into the campsite, but it was getting cold and dark at this point, and we were all so drained from that climb, we couldn’t fully enjoy it. We made it into camp at around 8pm, completely exhausted.

Day 5: Prineville, Help From Strangers, and a Visit to the ER

After packing up our things in the morning, we decided to bike down the road until we get enough cell service to text Bob. We were able to snag some service not far from the campground, so we told Bob about the big climb he was in for. We also mentioned that we were waiting for him at the campground. We were totally ok with having a mellow day after yesterday’s 86 mile ride.

While we were waiting at the campground’s entrance, we noticed a man driving a Prius pulling into the campground. He was coming from Bob’s direction. Shortly after, he started driving back the same way he came, so we decided to flag him down and tell him that we were waiting for Bob, just in case he ran into him on his way back. He said he would keep his eye out.

About 30 mins later, we saw the man’s car coming back down the road, with Bob’s bike tied to the windshield. Long story short, Bob had taken a bad slam going over a cattle guard. He was pretty beat up and was having trouble breathing, which obviously got us all super worried. Luckily, another man (Steve) who was camping with his wife overheard what was going on and immediately offered to drive Bob and Nick to the nearby hospital in Prineville, about 20 miles away. We quickly loaded up Bob and Nick’s bike into Steve’s truck and they headed to town. My dad and I rode our bikes into town and met them at the ER.

In addition to some road rash, Bob ended up fracturing 6 ribs. He would have to stay in the hospital for the next two nights, so we ended up getting a hotel room down the street. We were all pretty shaken up over the crash. I felt extremely bad that our group got separated the way it did. Ultimately, things could have been much worse, and I tried my best to keep that in mind while my head was swirling with all the various “what if” kinds of thoughts. We were really lucky to get help from the folks back at the campsite - we’ll all be forever grateful for the kindness and generosity we received from them.

Day 6: Good Bike Co. and Skookum Rock Bush Camp

While Bob was recovering at the hospital, we took the morning to figure out a game plan for the last few days of the trip. Ultimately, Nick decided that it would be best for him to stay back and hang with his dad while my dad and I finished the ride. We would rent a truck in The Dalles and then drive back to Prineville and pick up Nick and Bob before returning to Klamath Falls where my dad’s truck was. We were bummed that Nick would have to miss the rest of the ride, but everyone agreed it was the right move.

We decided to cruise downtown and stop at a cafe called Golden Coffee for some iced coffees and bagels. On our way there, we rode past an awesome skatepark + a rad pump track. I couldn’t resist taking a few laps. My son Jack would have loved this spot.

After some delicious coffees and FaceTiming with the fam, we headed to a local bike shop called Good Bike Co. We showed up right as the owner, James, was opening the store. This is hands down one of the coolest bike shops I’ve ever seen. James was incredibly cool and helpful. The shop has an amazing selection + a spot in the back to chill out - lots of electrical outlets for charging your stuff + a water faucet and bathroom. This place is basically heaven for cyclists doing the Oregon Outback.

Hannah, Meryn, and Brandon also rolled up while we were at the shop to get a few things + some tuneups on their bikes. James helped everyone out and was super accommodating.

I decided to treat myself a bit while we were here and picked up a Swift Industries frame bag + a shop water bottle. The frame bag is perfect for keeping somewhat heavy items towards the center of your bike. I was able to put tools, a pump, a bag of coffee from Golden Coffee, my wallet, plus a few other random items there.

We said goodbye to James and headed out towards Skookum Rock campground. Nick did the first half of the ride with us before turning back to hang with his dad. We were all bummed to see him leave the other way! It was a solid climb out of Prineville, but we were treated to a nice descent into the campground, where Hannah, Meryn, my dad and I set up camp. We chatted about other rides they had done in the past - Hannah told us about the Tree to Sea ride in Vancouver Island that she had done a while back, which sounds pretty epic.

That night while we were all sleeping, we heard what sounded like 20+ coyotes running around our tents and howling like crazy. It was pretty cool (and slightly nerve racking) to hear them romping around.

Day 7: Ashwood, Antelope, and Shaniko

After coffee & breakfast in the morning, we ran into Brandon and Nova (who unbeknownst to us, had reached the campsite a few hours later than us and camped at a spot not far down the road from where we were). We packed up our stuff and headed out towards Ashwood.

We had read about Ashwood having an amazing rest stop for cyclists, and it’s true! There’s a fridge & freezer that someone keeps stocked with cold drinks and ice cream for riders doing this ride. It’s all on the honor system and you just drop cash in a box they keep there. Whoever runs this thing (if you’re reading this) THANK YOU THANK YOU THANK YOU!

After guzzling some gatorades and ice cream sammies, we were ready to get back on the bikes. We were immediately greeted to a solid climb out of Ashwood. We made it to the top and Hannah snapped this cool group shot with a timer.

Our next stop was Antelope, and if that rings a bell for you, it might be because of the documentary Wild Wild Country - the story of the Rajhneesh, “a controversial cult leader who builds a utopian city in the Oregon desert, resulting in conflict with the locals that escalates into a national scandal.” The documentary is absolutely insane (check out the trailer here) and I couldn’t believe we were biking through the area where such wild shit went down. There wasn’t too much happening in Antelope, but there is an amazing rest stop for cyclists, similar to the one in Ashwood, so we pulled over for some popsicles and water.

We left Antelope and headed towards Shaniko, our final destination for the day. We had another little climb before getting to Shaniko, with one stretch of twisty road that I’ve seen pictures of before. The photos I took didn’t really do it justice - it was really picturesque and fun (even though we were climbing).

Shaniko was another small town, but there was more going on there than in Antelope. They had a few stores + a really cool old hotel that had just been renovated. After hitting the tiny grocery store, dad and I decided to crash at the hotel while the others camped at the nearby RV park.

Day 8: The Final Stretch

We woke up feeling rested after our stay at the hotel. We decided to get an early start because we had to make it to The Dalles by 5pm to pick up our rental truck. We biked over to the RV park and said goodbye to the others. It was so much fun getting to ride with them throughout the week - definitely a highlight of the trip!

The ride out of Shaniko was fun, but also slightly sketchy - there was a nice wide shoulder on the road, but the trucks were flying by pretty fast. We were stoked to get off that highway and back on the gravel.

We stopped for lunch in Grass Valley at an amazing little grocery store (Grass Valley Country Market) before starting the final stretch. The last few miles of the ride reminded me a lot of riding through Tracy & Livermore in the summer - everything was pretty dry and dusty, but there was an epic view of Mt Hood off in the distance, which was incredible. There were a few more climbs before reaching the top of the hills, East of the Deschutes River. Once we made it to the top, we saw some great views of the river before descending into the intersection of the Deschutes & The Columbia River Gorge.

We finally pulled into the Deschutes River State Recreation Area at around 2:50pm. We had finished the official Oregon Outback route, but we weren’t done yet. We still had to make it to The Dalles by 5pm to pick up the rental truck, which was about 20 miles away. We quickly refilled our water bottles and got back on our bikes. We were super tired at this point, but we had to keep riding + we had to keep our pace up. We were immediately greeted by an insane climb - we had to walk our bikes it was so steep. After that though, it was mostly downhill into The Dalles, so we made it to the Enterprise car rental at 4:30. We did it.

After loading up our bikes, we drove back to Prineville. After chatting with Bob for a bit at the hotel, we walked across the street to Wild Ride Brewing for a late dinner and celebratory beer.

8 days, 380ish miles - throughout this whole ride, I couldn’t help but reflect on how lucky I was to get to do this. It was super special to get to spend this time with my dad and experience such a crazy ride together. We’ve done a lot on bikes together over the years, but this one might just be the craziest.