Distance covered by motorcycle: ~530 km
Route: LaSalle, ON → Windsor Border → Detroit → Kalamazoo → Sawyer → Chicago → Homer Glen, IL
After a good night’s rest in LaSalle, the crew hit the road again just before 8 a.m., with the destination set for none other than Chicago — the official starting point of historic Route 66.
Into the U.S. – The Real Adventure Begins
Crossing the Windsor-Detroit border was smooth, though as always, the toll plaza and border checkpoint added a bit of a wait. But once across the Ambassador Bridge, the roads opened up into Michigan, and it finally felt like the adventure was kicking into high gear.
The first official stop stateside? Of course — a Tim Hortons in Belleville, MI. Old habits die hard.
Fuel for the Body and Soul
A few hours later, the group stopped at Gurdwara Singh Sabha of Kalamazoo, where the riders paused for a brief moment of calm. Sharing a spiritual meal, reconnecting with intention — this wasn’t just a trip about miles, but meaning.
Fueled up on food and faith, the group rolled through Sawyer, MI, topping off at Marathon Gas before the final push to Chicago.
Welcome to the Windy City
Rolling into downtown Chicago around 2 p.m., the eight bikes made quite a statement weaving past skyscrapers and honking cabs. First stop: Starbucks on South Michigan for a much-needed caffeine reload. Then it was time to officially mark the start of Route 66 at the Historic Route 66 Begin sign near Adams Street — the moment they’d all been planning for.
To celebrate? Deep dish, of course. The crew hit Giordano’s Pizza near the Rice Building, devouring layers of cheese and sauce like true road warriors.
Evening Ride to Homer Glen
After some tourist time at Navy Pier, the group rode out to Homer Glen, where friends hosted them for the night. The sun dipped low as they parked their bikes after a long but rewarding 530 km ride — tired, happy, and ready for the real Route 66 journey to begin.
🗺️ Highlights of the Day:
- Total motorcycle distance: ~530 km
- Riding hours: ~6 hrs 28 mins
- Border crossed: Canada → USA via Ambassador Bridge
- Stops of note:
- Gurdwara in Kalamazoo
- Deep-dish pizza at Giordano’s
- Route 66 sign photo-op in downtown Chicago
- Final stop: Homer Glen, IL