We wander through the artistic harbor town of Grand Marais, where local shops, lakeside views, and creative energy make it a must-stop destination. Then we cross into Wisconsin to experience the historic and welcoming vibe of Ashland, known as the gateway to adventure on the south shore.

Along the way, we chase some of the region’s most breathtaking waterfalls, from roadside cascades to hidden forest gems, and share tips on how to find the best ones. We also talk about the unforgettable experience of spotting lightning storms illuminating the iconic Apostle Islands—a natural light show you won’t soon forget.

Whether you're planning your own North Shore getaway or just dreaming of cool lake air and scenic views, this episode is packed with stories, travel ideas, and small-town charm from one of the Midwest’s most stunning regions.

So - take a road trip on Route-66 and check out all the small towns along the way - However - I highlight some within the states of Illinois, Missouri and Kansas.

I'd love to hear from you if you've ever driven Route 66! Drop a comment.

Check out these two towns -

Obviously, there are so many great small towns in each state - for this episode here are two --

#ashlandNebraska #MedoraNorthDakota

What actually makes a small town… a small town? Is it population size, a single stoplight, or the fact that everyone knows your business before you do? In this episode of Midwest Small Town, we dig into the many definitions of “small town” and why the answer depends on who you ask.

Along the way, we visit a handful of towns across the Midwest, comparing numbers, vibes, histories, and lived experiences. From blink-and-you-miss-it places to towns that feel small no matter how big they get, we explore what ties these communities together—and what sets them apart. Whether you grew up in a small town, or are just small-town curious, this episode sets the foundation for everything that comes next. 🌽🏘️

We dive into the hallowed halls of the Surf Ballroom, a venue that feels frozen in 1959. It wasn't just another stop on the "Winter Dance Party" tour; it became the stage for the final performances of Buddy Holly, Ritchie Valens, and J.P. "The Big Bopper" Richardson. ### What’s in this episode:

1. The Surf Ballroom: Explore the "cathedral of rock n' roll" and why its atmosphere remains unchanged decades later.
2. The Fateful Night: A look at the grueling 1959 tour conditions that led to the decision to charter a plane.
3. The Crash Site: We discuss the pilgrimage to the lonely North Iowa cornfield marked by the iconic oversized glasses, and what it means to fans today.
4. Clear Lake Today: How this community honors the tragedy while celebrating the vibrant, living history of the music that refused to die.

Whether you're a die-hard vinyl collector or a fan of Americana, join us as we walk the line between small-town charm and rock n' roll immortality.