Chicago To St Louis By Bike Via Route 66: Day 1-Chicago To Pontiac

Описание: 🚴‍♂️ Chicago to Pontiac on Route 66 by Bike | Day 1 of My Chicago to St. Louis Tour
Chicago and St. Louis are connected by Interstate 55… but the real adventure lies along historic Route 66 — America’s Mother Road.
In this first episode of my 4-day, 330-mile bike tour from Chicago to St. Louis, I set off from the official starting point of Route 66 at Adams & Michigan in downtown Chicago and ride 105 miles south to Pontiac.
2026 marks the 100th Anniversary of Route 66, and there’s no better time to experience this iconic 2,500-mile highway by bicycle. This ride highlights the history, roadside attractions, industrial landscapes, small towns, and preserved landmarks that define the heart and soul of the Mother Road.
Along the way, I pass through:
• Downtown Chicago landmarks and the Loop
• Historic Ogden Avenue (original Route 66 alignment)
• The scenic Centennial Trail & I&M Canal Trail
• Old Joliet Prison (filming location for The Blues Brothers)
• The Gemini Giant in Wilmington
• The Polk-A-Dot Drive In
• Classic restored gas stations in Dwight and Odell
• Route 66 murals and the Livingston County Courthouse in Pontiac
This stretch of Route 66 features cornfields, classic diners, Burma Shave signs, vintage Americana, and plenty of miles riding alongside Interstate 55 — a reminder of how the interstates changed the fate of this legendary highway.
If you love:
🚴‍♂️ Bike touring
🛣️ Historic highways
🇺🇸 Americana & roadside attractions
📍 Small town Midwest travel
…this ride is for you.
This is Day 1 of my Chicago to St. Louis Route 66 bike tour. Be sure to subscribe to Get Out And Bike to follow the remaining 230 miles as I continue south toward the Mississippi River and the Gateway to the West.

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