Your First Solo Tour Is the Ride That Changes You

Guiding You Through the Who, What, Where, When, and Why of Riding Alone

On a crisp October morning in 2018, I boarded the Amtrak Capitol Limited bound for Washington, D.C. The next day, I set out on a bike tour from the nation’s capital to Pittsburgh. I had completed it three times before, always sharing the adventure, joy, sense of discovery, and feeling of accomplishment with friends.

2018 was different from my tours prior to that year. It was my first solo inn-to-inn credit card tour, carrying the essentials and staying in Airbnb’s and hotels along the way.

I first rode the 3-2-1 Ride in Pittsburgh that supports pancreatic cancer research in 2017. That ride was personal, as one of my cycling friends’ wives was diagnosed with the disease. In 2018, her family again formed a team to ride in her honor.

I joined cycling friends for the 2018 edition of the 3-2-1 Ride. The ride’s metric century became the final leg of my journey from Washington, D.C. to Pittsburgh. My first solo tour transformed into something bigger, with an ending with a purpose.

My passion for bike touring took root in 2011, cycling those same trails with a friend on our very first cycling adventure. We camped and stayed in B&Bs while discovering the meaning of life on two wheels. That journey opened my eyes not just to the beauty of the outdoors but to the joy of slow travel and shared experiences.

That 2018 ride from D.C. to Pittsburgh became a turning point. It showed me how much freedom, reflection, and joy can come from exploring the world alone on my bike.

Answering The Call of Solo Touring

There’s a distinct quiet that emerges on a solo bike tour. The gentle hum of the wheels, the rhythm of your breathing, and the intimate way you experience the weather. Riding alone balances effort and ease, solitude and discovery. It’s in the miles that you come face-to-face with your strength and resilience.

This essay explores the who, what, where, when, and why of solo bike touring. Think of it as a guide and invitation for anyone who’s ever hesitated to take that first step alone. This collection of reflections is for those curious about how time spent on the bike can transform and enrich your life.

Who: Discovering Confidence Within

I never considered myself an adventurer, but I’ve always been eager to expand my view of the world. That solo bike tour in 2018 felt just as challenging as my very first bicycle tour in 2011.

As someone who often worries about safety, especially the possibility of being stranded in the wilderness, setting off alone on desolate trails was daunting. Overcoming that fear was a vital part of the journey.

I learned that touring solo isn’t reserved for the epic around-the-world bike tourists. Solo touring is for anyone searching for space to have honest inner conversations and striving for personal growth.

I wondered whether I could really handle it. That inner question was exactly why I got on the bike in Washington, D.C. and cycled westward. The answer would come over the 334 miles of pedal strokes.

A unique aspect was resetting my mindset to embrace the role of a beginner after seven years of experience touring with friends. I had to become someone willing to rely on myself and trust in my ability to achieve what I felt was out of reach for a cyclist like me.

The answer to “who” is simple: it’s you. Solo touring is about challenging the inner voice that says, “I can’t do this.” It’s a time to uncover courage from within.

Before setting out as a solo tourist, take inventory of the experiences, challenges, and achievements that have shaped your life and cycling. This foundation moves the voice to “I can do this ".

What: The True Meaning of Solo Touring

Finding meaning in solo bike touring is personal. For me, it’s the freedom of carrying only the essentials, making my own choices, and earning the satisfaction that comes from ending a day of touring smiling, tired, but proud.

Independence is a common reason cyclists tour solo, but a deeper reason comes from within. Solo touring quiets the noise of everyday life, allowing true questions about life’s purpose and change to surface. In that silence, clarity and focus emerge.

There’s a confidence that comes from handling whatever the journey brings, from fixing a flat in the rain, climbing a hill you thought was impossible, and discovering strength you never knew you had. These moments are about learning to trust yourself, your instincts, and your abilities.

Riding solo engages you in your life by not letting past limitations or others’ expectations set your boundaries. It’s about being persistent, present, and finding joy in meeting yourself and the world with every mile.

Everyone who rides solo finds their own “what,” their personal motivation. For me, planning and completing my first solo tour opened a new chapter in my life. Whatever reason calls you, hold onto it. That “what” will open a new chapter for you.

Where: Choosing Your Destination

Choosing where to undertake your first solo tour is a decision that begins with clarifying your motivations and goals while reflecting on what draws you to solo cycling and stepping outside of your comfort zone. An adventure doesn’t require travel to far-off places.

Rewarding experiences can be found close to home or on familiar routes. Expand a day ride into a longer tour to assess your self-reliance and cycling skills. Research routes that stretch your abilities just enough but prioritize comfort, safety, and being open to new experiences.

Choose a destination that matches the level of challenge you’re looking for and fits within your available time. Ensure it offers the amenities you’ll need each day and resources for when the unexpected happens. Look for routes, whether trails, roads, or a mix of both, that suit your cycling style while keeping safety your top priority.

Pick a place that excites you as a cyclist. Seek advice and inspiration from fellow cyclists whose experiences resonate with you. Let their stories shape and validate your choice. Once you settle on a destination, you can focus on planning the adventure that awaits.

When: Timing Your Solo Adventure

Deciding when to tour by bike is shaped by where you are in life and your priorities. In the past, work schedules and sharing vacation time with my husband dictated my options. In retirement, I still consult my calendar but focus on current and future goals as a person free from work constraints.

Practical considerations such as weather, season, lodging options, and road or trail traffic play a big role in planning. Except for winter getaways in Florida’s perfect cycling weather, I favor the shoulder seasons of spring and fall. These times have fewer crowds, easier booking, and vibrant colors that feed the senses.

“When” depends on aligning your life circumstances with the optimal season in your destination. By considering both thoughtfully, you can choose a window that lets you fully enjoy and appreciate your solo journey.

Why: The Power of Solitude and Growth

Choosing to embark on a solo bike tour weaves together the motivations and lessons behind all the other questions. The “why” becomes clearer in the days after that first journey. Touring is, at its heart, about discovery. Those discoveries confirm and deepen what you learned from riding solo.

Solo bike touring is a catalyst for personal growth. Pedaling solo gives you space to reflect, challenge old fears, and address the obstacles that hold you back. It forces you to confront discomfort and boredom while uncovering unexpected moments of joy and awe.

Solitude teaches in unexpected ways. It reveals a resilience and resourcefulness you never knew you possessed. It invites empathy and connection with people to engage you in conversation, helping you better understand the places and local flavors you encounter.

Every mile you ride solo tests your endurance and strength, helping you grow on and off the bike. The lessons learned of adaptability, perseverance, and self-reliance stay with you long after the tour ends.

Tom’s Closing Thoughts

If hesitation is holding you back, take some time to answer the five Ws. Start close to home with a one or two-night trip. These short tours help you learn the essentials of planning, packing, and handling the unexpected. Each tour builds your knowledge, confidence, and motivation to take on longer, more adventurous rides.