Cycling Through History: A Backroads Journey from Berlin to Prague
Most people dream of cycling trips through Italy’s sun-kissed hills or Spain’s sparkling islands. I’ve done both. In 2019, I rode the winding roads of Majorca and Menorca; in 2020, I pedaled past the vineyards and villas of Tuscany. Both trips were beautiful, classic in their charm, and populated with over 20 riders each—fellow travelers drawn to the well-trodden paths of Europe’s popular cycling routes.
But my most recent Backroads trip, a six-day journey from Berlin to Prague, was entirely different—and, perhaps surprisingly, my most memorable. With just four riders and two guides, the trip felt more like a personal expedition than a group tour. It was a deep dive into history, culture, and landscapes that often go unnoticed by those chasing Mediterranean sunshine.
We began under heavy skies in Berlin, at the famed 1936 Olympic Stadium—a haunting and powerful place to set off. It was drizzling as we clipped in and began our first ride, the kind of cold, persistent rain that might deter a less committed cyclist. But for us, it added an authenticity to the journey: we weren’t there for postcard perfection—we were there for something deeper.
The first two days took us through the East German countryside, a region still shaped by its post-war legacy. The terrain rolled gently, flanked by vast fields, thick forests, and villages that seemed unchanged for decades. The roads were nearly empty, giving us space to absorb the quiet beauty around us. Along the way, we stayed in magnificent countryside hotels—places with charm, history, and a kind of unexpected luxury that made each arrival feel earned. After a long day in the saddle, few things compare to sipping a crisp, fresh German beer on a terrace overlooking lush farmland while steam rises from your jersey and your legs slowly recover.
This was a far cry from the busy piazzas and tourist-packed cafes of Tuscany or the island charm of the Balearics. Instead of Mediterranean glamor, we found authenticity. Instead of crowds, quiet. And in that quiet, we connected more deeply—with the place, with each other, and with ourselves.
Midway through the trip, we reached Dresden, a city that embodies resilience. Nearly flattened during World War II, Dresden has been painstakingly restored, and its baroque beauty once again shines along the Elbe River. We visited the Frauenkirche, wandered cobblestone streets lined with palaces and opera houses, and unexpectedly found ourselves at a raucous American football game between the Dresden Monarchs and their rivals. It was a surreal but joyous cultural crossover—American sport played with German enthusiasm, beer steins in hand and bratwurst on the grill.
Our final day brought us into the Czech Republic, cycling alongside the Elbe River, its waters snaking through valleys and under low-hanging clouds. Though the skies remained stubbornly gray and the temperatures hovered around 60 degrees, the ride was sublime. Mist curled above the treetops. Villages dotted the riverbanks like scenes from old fairy tales. We stopped in towns where English was rare and dumplings and goulash were served steaming and heavy, perfect for cold-weather appetites.
What made this trip so special—more than the food, the beer, or even the stunning scenery—was its sense of discovery. While Majorca, Menorca, and Tuscany had offered beauty, they also came with a sense of predictability. This Berlin-to-Prague route was the opposite: unfamiliar, less polished, and steeped in history and contrast. The landscapes were bucolic, the stories complex, and the culture deeply rooted. Every meal was a culinary experiment—from sauerbraten and schnitzel to knedlíky and Czech pilsners. The gray skies, rather than dampening the mood, somehow heightened the experience. We were immersed in it, not distracted by it.
With only four riders, we became a small, tightly knit group. Conversations were deeper, the pace more relaxed, the support more personalized. There was room to pause, to explore, to reflect. There were no crowds waiting behind us at scenic overlooks. No pressure to rush to the next village. Just the rhythm of the pedals, the stories of the land, and the satisfaction of going somewhere most people skip.
As we rolled into Prague, its Gothic spires and red rooftops rising in the distance, I realized that this trip had offered something rare: the chance to go beyond the highlights reel of European travel. It was a ride into history, through a landscape shaped not just by beauty, but by resilience, complexity, and authenticity.
If you’re looking for postcard Europe, Italy or Greece might be the obvious choice. But if you’re seeking something more immersive, more off-the-beaten-path, and ultimately more rewarding, then the Berlin to Prague route is waiting. Even in the rain, it shines.