Uploaded March 2026 | Updated September 2026, 2 weeks ago
Planning a Route 66 road trip? Here’s the itinerary that actually works.
After driving nearly 2,500 miles from Chicago to Santa Monica, I put together two practical Route 66 itineraries based on the highlights of the Mother Road. In this episode of Photowalks, I break down how to experience the best of Route 66 whether you have two weeks, a week, or just a few days.
The plan takes you through the classic stops across Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California — with manageable driving days and plenty of time to explore the small towns, neon diners, roadside attractions, and photo spots that make Route 66 legendary.
Along the way you’ll visit places like:
• Chicago’s historic Route 66 starting point
• The Chain of Rocks Bridge in St. Louis
• Tulsa’s Art Deco downtown and neon
• Shamrock’s famous U-Drop Inn
• Cadillac Ranch in Amarillo
• The Route 66 Midpoint in Adrian, Texas
• Tucumcari’s incredible neon signs
• The Wigwam Motel in Arizona
• Oatman’s wild burros roaming the streets
• Roy’s Motel & Café in Amboy
• The famous “End of the Trail” sign at the Santa Monica Pier
Route 66 turns 100 years old in 2026, and there’s never been a better time to drive the Mother Road.
Chapters
00:00 Route 66 Road Trip Planning
01:03 The Perfect 2-Week Route 66 Itinerary
07:10 What If You Don’t Have Two Weeks?
07:47 Best Short Route 66 Road Trip
08:27 A 4-Day Route 66 Plan
08:48 Great 3-Day Route 66 Segments
09:10 Why Route 66 Matters
09:36 The Mother Road Legacy
#Route66
#Route66RoadTrip
#MotherRoad
#AmericanRoadTrip
#TravelUSA
#Photowalks
#RoadTripGuide
#HistoricRoute66
#ChicagoToLA
#Route66Itinerary
🔔 Explore the world through our lens on PhotoWalksTV! Subscribe now for breathtaking journeys and photography tips.: youtube.com/@PhotowalksTV/?sub_confirmation=1
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👉PhotowalksTV newsletter: photowalksTV.com
👉Website: jeffersongraham.com
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👉Instagram: instagram.com/photowalkstv
✅ For Business Inquiries: photowalkstv@gmail.com
⚠️DISCLAIMER: I do not accept any liability for any loss or damage incurred from you acting or not acting as a result of watching any of my publications. You acknowledge that you use the information I provide at your own risk. Do your own research.
Copyright Notice: This video and my YouTube channel contain dialogue, music, and images that are the property of PhotowalksTV. You are authorized to share the video link and channel and embed this video in your website or others as long as a link back to our YouTube channel is provided.
© PhotowalksTV with Jefferson Graham
Planning a Route 66 road trip? Here’s the itinerary that actually works.
After driving nearly 2,500 miles from Chicago to Santa Monica, I put together two practical Route 66 itineraries based on the highlights of the Mother Road. In this episode of Photowalks, I break down how to experience the best of Route 66 whether you have two weeks, a week, or just a few days.
The plan takes you through the classic stops across Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California — with manageable driving days and plenty of time to explore the small towns, neon diners, roadside attractions, and photo spots that make Route 66 legendary.
Along the way you’ll visit places like:
• Chicago’s historic Route 66 starting point
• The Chain of Rocks Bridge in St. Louis
• Tulsa’s Art Deco downtown and neon
• Shamrock’s famous U-Drop Inn
• Cadillac Ranch in Amarillo
• The Route 66 Midpoint in Adrian, Texas
• Tucumcari’s incredible neon signs
• The Wigwam Motel in Arizona
• Oatman’s wild burros roaming the streets
• Roy’s Motel & Café in Amboy
• The famous “End of the Trail” sign at the Santa Monica Pier
Route 66 turns 100 years old in 2026, and there’s never been a better time to drive the Mother Road.
Chapters
00:00 Route 66 Road Trip Planning
01:03 The Perfect 2-Week Route 66 Itinerary
07:10 What If You Don’t Have Two Weeks?
07:47 Best Short Route 66 Road Trip
08:27 A 4-Day Route 66 Plan
08:48 Great 3-Day Route 66 Segments
09:10 Why Route 66 Matters
09:36 The Mother Road Legacy
#Route66
#Route66RoadTrip
#MotherRoad
#AmericanRoadTrip
#TravelUSA
#Photowalks
#RoadTripGuide
#HistoricRoute66
#ChicagoToLA
#Route66Itinerary
🔔 Explore the world through our lens on PhotoWalksTV! Subscribe now for breathtaking journeys and photography tips.: youtube.com/@PhotowalksTV/?sub_confirmation=1
hotowalksTV.
👉PhotowalksTV newsletter: photowalksTV.com
👉Website: jeffersongraham.com
👉Facebook: facebook.com/PhotowalksTV
👉Instagram: instagram.com/photowalkstv
✅ For Business Inquiries: photowalkstv@gmail.com
⚠️DISCLAIMER: I do not accept any liability for any loss or damage incurred from you acting or not acting as a result of watching any of my publications. You acknowledge that you use the information I provide at your own risk. Do your own research.
Copyright Notice: This video and my YouTube channel contain dialogue, music, and images that are the property of PhotowalksTV. You are authorized to share the video link and channel and embed this video in your website or others as long as a link back to our YouTube channel is provided.
© PhotowalksTV with Jefferson Graham
