Despite our most romantic visions, not all bikepacking endeavors are blessed with blue skies, top-notch trails and vistas that rival any others. The reality is that on occasion, even your best-laid plans prove to be fraught with obstacles, sending you on unexpected detours or back the way you came day after day. Getting booted off the more-traveled path and into lesser-known country can end up being a blessing in disguise or a curse, depending on the outcome. But that sense of uncertainty and the imposed fly-by-the-seat-of-your-pants mentality is where real adventure can begin, should you let yourself embrace it.

Recently, I found myself on a plane to Scotland, recruited to work the pits for a couple friends who were racing the Solo 24 Hour World Championships in Fort William. I was eager to have the opportunity to head over a bit early for a week of bikepacking in the rugged and beautiful Highlands, and I put together a route that would lead me out of Glasgow and meander through some of the country's most mountainous landscapes before delivering me to Fort William. And from what I was told, the fickle autumn weather would hold the blood-thirsty midges at bay, and it'd likely be grey and rainy. But from the moment I stepped onto the first airplane of the trip in Phoenix, things began to go awry, and that pattern continued with a missing bike, a cold tropical storm, uncrossable rivers and gale-force winds.

Arriving in Glasgow a day later than planned due to flight delays and then spending another day holed up in the city was not how I had envisioned my arrival to Scotland playing out. Amid the flight changes, my checked bike case hadn't kept pace with me, so I sat in a hotel room, catching up on sleep and staring at the window as Tropical Storm Callum lashed out with strong winds, pounding rain and chilly temperatures. I was actually relieved to not be out trying to ride in the storm, but it pained me knowing that a couple days of riding time were being excised from my trip. As the storm subsided, my bike finally arrived and I opted to hitch a ride north rather than riding out of the city as planned. Down to five days, I wanted to maximize my time in the higher country, so it was on to Plan B, starting a bit farther north right in the mountains.

I got dropped off in a lush, nearly treeless valley lined by rounded mountain peaks. Most of the forests in the Highlands were logged during World War II, so much of it resembles what I would imagine Appalachia looking like if all its trees were stripped away and replaced by tundra. Rain was still falling, and as soon as I left the road, I was splashing along a flooded farm track. Water was running down the hillsides in sheets, and the sheep looked as if they'd just climbed from a lake. A mile in, I turned onto a smaller track, passed a farm house and stopped in disbelief. What I expected to be a small stream was a roaring river that had swelled well over its banks. I looked at my map – it showed three crossings in the next half mile, and I didn't stand a chance at surviving even a single crossing. I turned around and pedaled back to the highway, resigned to moving onto Plan C. I just had to figure out what that plan might be.

When Plans A, B and C fail, the universe has to give you a pickle at some point. Getting out of the elements after a day of slogging through continuous puddles is a welcome relief—especially if there’s a good view.

The next afternoon, I got dropped off farther east at the northern edge of the Cairngorm Mountains—Plan C meant diving into the big mountains straight away and looping circuitously through them on somewhat primitive trails and two-tracks. Farther inland, the region is a bit drier, and a local guide thought that I'd find more cooperative conditions there. Into the mountains, I pedaled beneath a sky that began to show scattered patches of blue. The air was crisp and thick with moisture. I carried food for four days, a decision that ultimately gave me the flexibility to avoid passing through any communities to resupply. The holes in the grey cloud cover grew as I climbed out of the forest, following a steep but well-built trail. Subdued summits loomed just below the clouds, and as I crested a broad pass, the sun, already low in the southwestern sky, came out. Before long, it dropped behind a ridgeline and my trail quickly degraded as it traversed into the shade.

I spent the last hours of daylight bouncing over rounded boulders and splashing through the nearly continuous puddles down into a desolate valley colored golden by shin-tall grass. The Fords of Avon was my planned destination for the night, a river crossing that I hoped might still be manageable after the recent rains. But as dusk arrived, I could hear the roar of whitewater, and my heart sank when the river came into view. There would be no fording. Deflated, I retreated into a nearby refuge hut, little more than a wooden shed armored against the wind on three sides with stacked boulders. I pored over my topographic map as I heated up tea and dinner and constructed Plan D: climbing higher into the mountains in an attempt to cross the river closer to its headwaters. I had a hunch my bike would get to ride on my back going that route given how tightly the map's contour lines clung to one another.

Top: Bikepacking usually turns into bikehiking. Bottom: Two nights, two different trail-hotels.

The late sunrise bathed the landscape in a bright orange glow as I pushed my bike up a boulder trail above the still-raging river. This was not a heavily traveled trail, but as the head of the valley came into view, I grinned widely. Cascading creeks plunged a thousand feet down steep rock faces and granite turrets towered above a deep blue lake. The overwhelming magnitude and challenge of this place what I hoped to find in the Highlands: a thigh-deep river crossing, a treacherous bike carry to ascend a pass, then a rubbly descent into the cliff-lined valley far, far below. And I wouldn't have found any of it had I not been forced on to Plan D.

Going off the planned route can sometimes lead to places you would have never found otherwise.

That evening, I camped on soggy ground surrounded by orange autumn foliage in a narrow canyon with just enough cell signal to check the mountain weather forecast. My jaw dropped reading that the following day would have winds of 60 to 70 miles per hour at the 900-meter level! Climbing back among the peaks suddenly seemed unwise, so I pulled the maps back out to create Plan E: stay low among the forests and finger lakes, aiming toward the Grampain Mountains farther west instead. Battling gusty winds and intermittent squalls at far lower elevations proved to be the prudent decision, and I thoroughly enjoyed the challenge of following faint public paths that meandered through pastures, down farm driveways, through back yards and among conifer plantations. These old rights of way through private property are common throughout the United Kingdom, and unlike farther south, mountain bikes are welcomed on these paths throughout the Highlands—everyone I saw along the way waved with a smile and then continued about their business.

A fully loaded bike may keep the weight off your back, but saturated peat moss doesn’t care where the weight comes from—it’ll eat your tires either way.

My final day of riding involved climbing over the Grampians back toward Fort William after a night of steady rain. The over-saturated ground oozed as I pushed my bike along boggy trails. Even attempting to ride would sink the bike halfway to the hubs in peat moss, so I walked and admired the grey ambiance that enveloped my surroundings. A pair of very muddy runners I had encountered the prior evening, also out "bog trotting," suggested that I push my bike over a nearby pass to visit a particularly scenic lake. The descent beyond, they told me with clear excitement, was one of the best around on a bike. An alpine lake and another stellar downhill? I was sold. The trail wasn't on my map, but I took their word that I'd be able to make my way through and shouldn't encounter any substantial river crossings. Onto Plan F…

Plan F—not bad. Not bad at all.

And Plan F did not disappoint. Upon reaching the top of the two-hour-long and very soggy hike, the surrounding peaks, flanked by cliffs, abruptly emerged from the clouds as a rainbow spread over the lake. I stood in awe in complete silence, so thankful that I hadn't been able to stick to any of the prior plans. Not a single one of them would have brought me to that particular pass, nor would I have ended up puzzling my way through scenic farmsteads and colorful forests or carrying my bike into the high country. And the ensuing descent was nothing short of icing on the cake. I'm sure my original route plan would have been beautiful and enjoyable, but the uncertain nature of what unfolded each day and embracing it rather than becoming frustrated with being repeatedly stymied made the experience all that much more rewarding.