Cycling paths are usually known for their scenery. And while this can be all romantic and pretty, sometimes even breathtaking, some bike trails are more than that. They can be a full-blown landmark infused with histories, cultures, and transformations. Some places were made for something else, with bike-friendliness not being a high priority (or any priority at all). Regardless, they still ended up being some of the most popular routes for cyclists.
Why these cycling landmarks matter is that they teach us that a bike ride is more than just a new experience or scenery; it can be about transformed space, like in The 606 of Chicago. Sometimes it can be about the past, like the remains of Kinzua Bridge. It can also be about experiencing places that you can only do on a bike, something like seeing the ocean on the Shimanami Kaido. These landmarks are proving that you don’t have to build something new to create a new investment. Reimagining what already exists is a true art. Here we will show you, from vintage railways to city bridges (and back), all cycling routes that are defined by stories as fascinating as the rides themselves.
1. The 606, Chicago
High above the northwest Chicago streets was an old rail corridor. Its purpose was to carry freight trains along factories and neighborhoods. In the 1990s, the corridor was unsafe and abandoned. People thought that it was going to be torn down, but that wasn’t the case. The city found a new purpose for the old corridor. It became The 606. It is an elevated greenway now filled with cyclists, joggers, and strollers.
It is wonderful how something abandoned and useless turned into a community space. It is decorated with murals and lined with trees. Beautiful and different, but there are some complexities. Cycling there means you need to share space with traffic and go through intersections – never ideal.
In those conditions, unfortunately, accidents may happen. And in a city where cycling has experienced an unprecedented/exponential growth rate in a very short amount of time, the infrastructure, naturally, wasn’t able to keep up. So keep in mind that while you can take all the precautionary steps that you can (alertness, safety, gear, caution, reflective gear, lights, etc.), you’re still only 50% of the ‘accident’ equation. The other person that’ll be involved in a bike-related accident (car driver, another cyclist, a pedestrian, etc.) will be something that YOU cannot control. What you can control, though, is to help advocate for safer streets and fight for more awareness, especially regarding trails that are growing in popularity at this rate. Only experienced and specialized bicycle injury lawyers will help you not only get justice and compensation, but also make the trail perpetually safer.
2. Kinzua Bridge, Pennsylvania
Before, it was considered one of the world’s highest railway bridges. The Kinzua Bridge carried trains over a valley, but it was destroyed when a tornado wrecked almost everything in 2003. The state didn’t destroy what was left. What they’ve done is they transformed it into a skywalk and biking attraction. For cyclists, this is great for riding up to the edge of a steel construction with glass floors. This attraction is unique because you can see the valley floor below.
3. Shimanami Kaido, Japan
Did you hear about six small islands in Japan with a series of soaring bridges? If the answer is ‘no’, you need to hear about them! Shimanami Kaido was built for vehicles, but soon became popular among cyclists. Because of that, special lanes were added to make cyclists feel like they are flying over the water. What’s interesting is that this landmark’s infrastructure was made for speed, but now creates a slow travel experience. Cyclists can stop in fishing villages, see shrines, and look at the ocean. The Kaido is more than a connection between places. It’s really an invitation to linger.
4. Conquer the Classic Cobblestone Climbs
If you want a European experience, then you should dive into the heart of cycling history by tackling the legendary cobblestone sectors of Western Europe. This is more than just hills because they’re grueling stretches of pavement that demand precision, extreme power, and dedicated grit. If you imagine the roar of the crowds as you cycle the Muur van Geraardsbergen in Belgium, or perhaps you tackle the Carrefour de l’Arbre in northern France, as you etch your name alongside the Flandrian heroes of the Spring Classics. This adventure is a brutal but beautiful test of bike handling and endurance.
5. Embark on a Self-Supported Bikepacking Odyssey
Those adventurous enough to strip away the sag wagons and luxury hotels can experience the ultimate test of independence through a self-supported bikepacking trip. You can plan a multi-day route through remote wilderness, carrying everything you need: a tent, food, and a repair kit, on your bike. Whether it’s the Continental Divide Trail or a rugged local forest somewhere in North America, this journey will teach you about minimalist living, as you navigate by the stars, and rediscover the sheer joy of simplicity and resourcefulness on two wheels. This will also force you to discover the hidden history about the places you visit and experience in person.
6. Chase the Dawn Across the Coastal Trails
A different kind of adventure would be if you decide to experience the meditative rhythm of the sea by taking a multi-day coastal tour. As you cycle along dramatic cliffs, through charming fishing villages, and alongside pristine beaches, you will feel the salty air, the views will become expansive, and the challenge will be in the relentless head or tailwinds. If you picture yourself cresting a rise just as the morning sun breaks over the ocean, you will simply feel the exhilaration of covering vast distances powered purely by your legs and the stunning scenery. As our coasts are constantly shaped by the never-ending sea-waves, they can transport you to a historic time when the first settlers discovered the Americas or Australia.
7. Master the Technicality of Enduro Mountain Biking
Switch the pavement for technical singletrack and steep descents that demand focus and commitment. An Enduro adventure involves challenging climbs followed by exhilarating, timed downhill sections. From the root-strewn forests of the Pacific Northwest to the rock gardens of the Alps, this is a mastery of gravity and machine. It’s a high-adrenaline dance on two wheels, where precision and fearless cornering are the keys to glory. Even though this form of cycling is new, and it has been with us for several decades, you can still experience what the first pioneers experienced when they started this taxing form of cycling.
8. Immerse Yourself in a Historic Grand Tour Route
Follow the tracks of the professional peloton by riding one of the iconic stages of the Giro d’Italia, Vuelta a España, or Tour de France in a single day. Select a stage defined by a legendary, summit finish, like the Col du Galibier or the Passo dello Stelvio. Even though some would think that this is about the climb, on the contrary, it’s about the deep connection to cycling’s heritage, feeling the pain and elation that champions before you have felt behind. As they are more than 100 years old, there have been many legends that have taken this challenge and proved to the world that everyone can improve and be better at anything, even cycling the Tour de France.
9. Cycle the Extremes: The Frozen Landscapes
For a truly unique challenge, you have to gear up for an expedition across a frozen landscape or a remote winter trail. By using fat bikes with specialized tires that can withstand extreme weather, you’ll glide silently over snow-covered ground and frozen lakes, as you’ll push the limits of cold-weather endurance and experience something that others would not dare doing. As this adventure is a battle against the elements, the end result will be quite rewarding for you in the sense that it will be an eerie, beautiful experience of solitude and a profound sense of accomplishment in conquering nature’s harshest conditions.
10. Achieve a ‘Fastest Known Time’ (FKT) on a Local Icon
Turn a familiar route into a personal challenge by attempting a Fastest Known Time (FKT) on a significant local segment or climb. Known as the purest form of self-competition, due to its demanding meticulous preparation, pacing strategy, and an all-out effort, this is going to make you push your limits. Overall, it is a chance to put your training to the ultimate test, shatter personal barriers, and earn local bragging rights by leaving your absolute best effort on the road or trail.
In conclusion, cyclists cycle and they always move forward. This means that they require a secure trail and are at least somewhat bike-friendly. But if that trail is also continuously filled with a bunch of features that those same cyclists get to enjoy while on the trail, then that trail can easily become a cycling landmark. These examples we’ve covered are only a small drop in the ocean of the landmark cycling trails that the world has to offer, and it’s up to us to discover them all. When bridges, hills, or forgotten rail lines take on a new meaning, they can be turned into the most beautiful landmarks for cyclists to experience nowadays. Each of these cycling trips is a story waiting to be told, and when you are on the bike, you’re a part of that story.