Rollins Pass Adventure Ride

Written by Scott Tribby (07/2021)

“Adventure should have an uncertain outcome” - Dan Milner

The great thing about adventure is that it comes in many forms and is experienced differently by anyone who participates. I firmly believe it should involve some sort of risk or adversity from which could come success, failure, introspection, and learning. For all of us who ride bikes, I think we can recall many times in which two wheels has put us in these situations (externally, internally, or more likely both).

I’m not sure I’m up for this….at least that was the phrase on repeat in my head in the days leading up to the Rollins Pass ride. Imposter syndrome is something I suffer from often, and “faking it until you make it” is only useful in particular situations, certainly not in an endeavor in which physical and mental shortcomings will be laid bare should you show up unprepared.


This ride had been on my list for awhile, but I knew little about it other than it was rough terrain that rewarded you with great views at the top. I had no doubt that I could ride to the top of the pass and back down. But, when TJ posted the route going all the way to Winter Park and back, that was a little more than intimidating. I knew riding my mountain bike was the better option (rather than my gravel bike). However, I’d never ridden it for longer than 4-5hrs at a time. How it would feel, or more correctly how my body would feel, was the question.


Let’s be clear, while I was nervous and full of self-doubt, the final outcome was never really in question. I would survive, most likely complete the route, and arrive back home safely. The outcomes I was unsure about were: How would I hold up mentally when the real suffering began? Would my body trick my mind into giving up? Would I let down or embarrass myself in front of the group?

The group which assembled early that Saturday morning was one of familiar faces, some new and a whole hell of a lot of Jorts! It was reassuring to be riding with people that I’d become somewhat familiar with….TJ, Ty, Jake, Libby, John, and many others. Everyone was in good spirits and ready to tackle the road ahead, literally as well as figuratively. As an adventure ride should go, the “rule” was that we would regroup in Winter Park (at the hot dog stand of course!) before heading out on the ride back over the pass. Little did I know how important that would be for me at the time.

The ride up Rollins Pass road was a rough slog through jagged lines and baby head rock gardens. There was a jovial mood about the group, though, as evidenced by almost every rider’s smile and pumped fist as I took pics along the way. The happiness that comes with riding a bike and sharing that experience with others was obvious. The larger group splintered quickly into smaller ones, but I don’t ever recall seeing a lone rider left out on their own.


As we began to get closer to tree line, the landscape became more spectacular…small alpine lakes, rock features, and vistas that made me stop and take notice more than once. At this point I felt pretty good, although stopping to take pics and then having to push to get back to the group numerous times did start to take its toll. I’m not a talented or strong rider, it's always a struggle it seems. That being said, I felt like I had my legs (and lungs) that day, so I was pretty pleased with how the day was progressing.

Our ascent up to the tunnel, and subsequent hike-a-bike over it, provided a breathtaking view of lakes and mountain peaks. While I'm not a fan of having to carry my bike, those views definitely made it worth it. There was a small sense of achievement and joy within the group at that point, and we all took a few minutes to soak it in, grab a bite to eat, and share smiles and small anecdotes about the ride so far (and of course tons of pics). We slowly made our way across the rock infested terrain and onto the short trail that would take us to the the famed train trestle.


Up until this point, we pretty much had the road to ourselves. But, that began to change quickly. It was approaching midday, and groups of people started to emerge ahead and behind of us. TJ, Leo and I spent a few fun-filled minutes getting choice shots of one another riding across the trestle, but the human traffic started to increase and we still had a long day ahead. A few short minutes of climbing up to the top of the pass, and we began the glorious descent into Winter Park.

To call that view breathtaking would be a gross understatement. The gravel road on the Winter Park side was like pavement compared to Rollins Pass road. So, on my MTB I could somewhat relax and be a little bit more playful with my riding. I got some good shots during the descent, including Jake’s usual child-like enthusiasm, Libby’s infectious smile no matter what she seems to be doing, and TJ cursing his chain after losing it multiple times on the way down.


The posted route linked up with some flowy single track as you approached Winter Park, but I knew that there were MTB trails starting even higher up, and was determined to take advantage

of being on a full suspension bike. At the first sighting of a trail branching off from the road, I took my chance and headed down on my own. Winter Park did not disappoint, the trails twisting and weaving their way down the aspen covered mountainside, inviting my bike to hit every feature it could on the descent. Fast tech, some rock gardens, smooth berms, and even a few short, punchy climbs…it all definitely made the ride (so far) worth it! While it probably added an extra 30 minutes (minimum) to my ride time, it made the ride down so much more fun.


Meanwhile, back at the hotdog stand, I met up with a portion of the group that was taking a breather and partaking in the food before heading back. I joined in, with the intent to head back once the group I’d been with arrived and was ready to head back. TJ, Jake and Libby arrived shortly after (Libby taking a spectacular digger on the side walk literally a couple of hundred feet from the hotdog stand). We all ate, drank, and let our legs get some downtime before heading back out… just as some weather started to roll in.

As soon as I got back on the bike and started to climb, I knew the ride back was going to be a trial. My 30-45 minute descent on the MTB trails had cooked my quads more than I’d realized, and every pedal stroke uphill felt like a slog. Then it began to rain. My body was tired, wet, and losing steam quickly. The group, which now included Dom and Kari from ThankgravelitsFriday, quickly started to pull away from me. I knew what pace I needed to maintain over the long haul as to not blow myself up. So, I resigned myself to the idea that I’d be riding most of the way back solo.

It was only a few minutes however, before I caught up with the group as they stopped to ditch their rain gear, as the rain had finally subsided. We headed off again, and again I got dropped rather quickly. But I caught them again as they stopped for a quick snack (or so I thought). This happened one more time before I realized what they were doing…they were waiting for me to catch up so that I wouldn’t spend the whole ride by myself without any support or company. At one point Dom dropped back and rode with me for awhile, our conversation helping to take my mind off of the suffering. To this day I am grateful to this group for what they did. Not only because it made my ride back more bearable, but because it also tempered the sense of isolation that is inevitable on the bike at times (sometimes welcome, sometimes not).


The final couple of miles up to the pass offered up stunning views of the mountains. The afternoon clouds cast dark shadows down upon them, creating a greater sense of drama and depth. More than once we stopped to soak it in and take pics, while at the same time giving our bodies a break. At this point we were approaching 8hrs in the saddle and still had a long, rocky descent ahead which would be taxing in its own right.

The sun was starting to get low in the sky, and as we came upon the trestle it lit up a cluster of large, puffy white clouds in the distance. We had the entire area to ourselves, and I think the scene pretty much took everyone’s breath away for a moment. Group pics were had, and as everyone started to ride across I made a point to get some more shots as well. It really is an iconic scene, and I was glad to have been given the chance to experience it with this group with no one else around.

Riding back down Rollins Pass road was “fun” for the most part on a full suspension MTB, as I could keep my speed up and let the bike eat up a lot of the terrain. With that being said, it still took a toll on my arms after awhile because of the sheer amount of vibration over such a long distance. I can only imagine how it was for those in the group who were on gravel bikes. They had to pick their lines much more carefully, lest they suffer a flat or worse, crash down onto the unforgiving surface.

Dom and I took a few opportunities to burst ahead of the group on our MTBs, and then would wait for them to catch up (returning the courtesy they had shown me previously). We were all chasing the remaining daylight, which was starting to fade fairly quickly. None of us wanted to be trying to descend as the darkness approached (I for one didn’t bring a light), but at the same time had to make sure we made it down safely considering the terrain.

As we rounded the last turn before reaching the bottom, the valley below greeted us in spectacular form. This would be our last stop as a group before parting ways to get back to our respective cars. I took the opportunity to get some shots of the valley and surrounding mountains, the fading sun casting shards of light onto the landscape below. The scene seemed to lift the spirits of everyone as we reflected on the day’s journey and said our goodbyes. With the sun fully set and dusk upon us, we chased the light down the road to Rollinsville and home.