I Am Virtually Walking Route 66, and I Can’t Say Enough About the Experience

This is the story of how I got my lazy self up off my cozy couch last spring and have walked over 1,900 miles (and counting) along an iconic American trail. I have explored roadside attractions, visited nostalgic restaurants and hotels, and traveled to numerous historic sites, but haven't even needed to leave my neighborhood to do so. How is this possible, you might ask? Well, all that is required is my cell phone and a good pair of sneakers.

Last year, New England experienced a particularly cold and windy winter, and by the time March rolled around, I was in dire need of some exercise. However, I just couldn’t muster up the motivation to leave the comfort of my warm, comfy home and brave the never-ending harsh weather. That is when I came across an ad for The Conqueror Virtual Challenges exercise app, which turned out to be a game-changer. 

I researched the Conqueror app and learned how it works. Participants pick a popular travel route and walk it virtually by logging steps from daily exercise completed anywhere. Challengers set their own time limit to complete the route and receive a themed medal at the end of the journey. The route, miles, time, and percentage of completion are all tracked within the app. 

This all sounded easy enough, but I have to admit I was a little skeptical about signing up for a challenge. I didn’t really see the point in virtually walking to a destination when I could just go and visit it myself. However, as I mentioned above, I needed the motivation, and it was either this or a Couch to 5K, and that certainly wasn’t happening. So I skimmed the numerous challenge options, which ranged from Rome to the Appalachian Trail, and decided to get my money's worth by purchasing the longest available challenge, the 2,280-mile Route 66.

I’d always been intrigued by tales of the historic road, but had never visited any of the sites along the way. In fact, except for travelling to Illinois years ago, this part of the country was brand new territory for me. I was excited to see what was in store. Since Route 66 is a very long challenge, I set my goal completion date for the maximum allowed time, two years from the start date. On the first day of spring, I strapped on my sneakers and excitedly hit the pavement running (well, actually walking) as I began my virtual journey at the start of Route 66, blocks away from the Willis Tower (formerly the Sears Tower) in Chicago.

Everything was going great until I sadly realized I wasn't traveling enough miles per day to meet my hefty mile goal within the allotted two-year period. The app kept telling me I was falling further and further behind, even though I always made an effort to walk 2 to 3 miles a day. Looking back, I realized that I should have started with a much shorter challenge.

But I was miles into Route 66, and there was no turning back, so I searched the Conqueror website for a way to resolve this issue. I discovered that I could still reach my goal if I formed a team of various challengers who work together to walk the allotted miles. Through the app, participants can form teams with random members or pair up with a friend. Lucky for me, my husband decided to step up and join me on my journey,

Because he runs regularly, we were able to regain the miles I had lost and were quickly on track to complete the challenge. In fact, before we knew it, we were actually ahead of the game. So far, we have travelled across eight states, and we are currently 86% of the way through the challenge. In fact, we haven’t even hit the one-year mark, never mind year two! 

I was completely surprised at how much fun this challenge turned out to be and how invested I have become in exploring this historic road. Every morning, my husband and I log our individual steps from the previous day and check the app's map to see where we are on the route. As we move through big cities and small towns, we pass by so many interesting landmarks (which we can get a detailed view of by clicking a Google Maps link). Every so often, we receive an alert that wehave earned a personalized virtual postcard with fun facts about an attraction. My favorite so far is Slug Bug Ranch, a quirky roadside attraction near Amarillo, Texas, where visitors can spray paint old Volkswagen Beetles.

My virtual journey has also piqued my interest in discovering more about this historic road. I recently learned that 2026 marks the 100th anniversary of Route 66, a road originally designed for farmers to transport goods between small towns and large cities and later an easy, scenic route for travellers to drive from Chicago to Los Angeles. The route's nostalgic hotels, diners, and roadside oddities now draw millions of visitors each year.

I can honestly say that the virtual challenge was one of my best purchases of 2025. It has been a great motivator to get out and exercise, and it has become a fun way for my husband and me to spend time together. I have learned a lot about places that I would never have thought to visit, so much so that we are considering taking an actual trip to see parts of Route 66. When the time comes, I plan to make the most of this adventure by mapping out our itinerary using the Only In Your State customized travel planner.

So what happens after we reach the Santa Monica Pier in California and receive our long-awaited finisher's medal? I can tell you for sure that we will be signing up for another challenge. Which one? Well, the possibilities are virtually limitless. Perhaps a European route, such as London or Vienna, or maybe we will decide to hike the Grand Canyon. There are even themed challenges, such as the Lord of the Rings and the Looney Tunes Series.

Have you completed a virtual exercise challenge? Where did your travels take you? If you would like to learn more about virtually walking Route 66 or other routes, please visit The Conqueror Virtual Challenges website and The Conqueror Challenges Facebook page. And if you would like to take a real-life journey across historic Route 66, you can set off on this ultimate road trip and visit 20 iconic roadside attractions.