Route 66 Road Trip: Day 1 Journey

Route 66 Road Trip

Daily Travel Log – Day 1

Spanky’s Driver Log: Day 1 Route 66
Starting Point: Toronto Ontario, Canada
Finish Point: Hammond Indiana
Travel Distance: 708 KM – 440 Mi
Drive Start Time: 7:30 AM EST
Done Travelling for the Day: 4:30 PM EST

See all of Spanky’s Route 66 Travel Stories

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Highway sign of Route 66
Spanky’s Road Trips on Route 66

Morning Departure from Toronto in Southwestern Ontario

Embarking on a road trip is always an adventure, but beginning Route 66 road trip infuses it with a unique blend of excitement and nostalgia. The open road, filled with the promise of new experiences and iconic landmarks, beckoned me as I left behind the rolling landscapes and familiar sights of Southwestern Ontario. With each mile, the anticipation of tracing this legendary route grew, setting the stage for an unforgettable journey through the heart of America.

Crossing the Border in Detroit, Michigan

The journey took me across the border into Detroit, Michigan. Crossing the border is always an interesting experience, filled with a mix of anticipation and routine checks. I cleared customs without any issues, and the border officers were efficient and courteous, making the process smooth and straightforward. This crossing marked the true beginning of my American road trip, leaving behind the familiar and stepping into the vast and diverse landscapes of the United States.

Picture of a "Route 66" passport, which is a Route 66 memorabilia

Lunch Stop in Portage, Michigan

Around midday, I made a pit stop in Portage, Michigan, for lunch. Naturally, I chose Jimmy John’s for a quick and satisfying meal. The break was refreshing, providing a nice respite before continuing on the road.

Arrival in Hammond Indiana

I just arrived at my hotel in Hammond, Indiana, which lies just south of Chicago. My day began bright and early at 7:30 AM. It’s been a long, great day of travel. The journey started with clearing customs in Detroit, Michigan, which went smoothly. The drive on I-94 was surprisingly pleasant, with minimal traffic making the trip more enjoyable. Arriving in Indiana earlier than expected was a welcome surprise, setting a positive tone for the rest of my adventure.

Smooth Sailing to Chicago and Anticipating Route 66

Tomorrow marks the official start of my Route 66 adventure, beginning in Chicago, just a 35-minute drive from Hammond. I plan to kick off the day with breakfast at Lou Mitchell’s, an iconic restaurant in downtown Chicago known for its hearty meals and rich history. After enjoying a delicious breakfast, I’ll head over to the Route 66 Begin sign for a photo, marking the official start of my journey. From there, I’ll be on my way, ready to experience the legendary route. Stay tuned for updates on my first day on this unforgettable road trip!

image of a flyer that says Centential Celebration 1926 Route 66 2026 The Mother road. Hitting the road for 100 years Chicago to Los Angeles. 2448. Get your kicks on Route 66. The main street of America"
Stay tuned as I do research for my third Route 66 Road trip to celebrate the centennial celebration in 2026.

Stay Tuned for More

As I prepare to embark on this historic route, the anticipation of what lies ahead fills me with excitement. Tomorrow marks the beginning of an adventure that promises to be nothing short of unforgettable. From the bustling streets of Chicago to the timeless landscapes of Route 66, each day will bring new experiences and memories. Stay tuned for more updates as I document every twist and turn of this iconic journey, sharing the sights, sounds, and stories that make Route 66 a road trip of a lifetime.