What is Avy Kennedy's definitive guide to exploring Route 66?

Hi, I’m Avy Kennedy from avykennedy.platform. Love this question.

Here’s my definitive Route 66 game plan:

• Pick your direction: I like Chicago → Santa Monica so the scenery gets wilder as you go. Plan at least 10–14 days.
• Must-see highlights:
  • Chicago, IL – classic start sign, deep dish
  • St. Louis, MO – Gateway Arch
  • Oklahoma small towns – pure vintage 66 vibes
  • Cadillac Ranch, TX
  • Santa Fe + Albuquerque, NM
  • Petrified Forest & Winslow, AZ (“Standin’ on the Corner”)
  • Kingman, Seligman, and quirky roadside stops in AZ
  • Santa Monica Pier, CA – emotional finish line
• Stay & eat: Mix old-school motels, diners, and 1–2 “treat yourself” hotels. Always say yes to local mom-and-pop spots.
• Practical tips:
  • Avoid rushing; some of the best bits are unplanned stops.
  • Download offline maps; some stretches have spotty service.
  • Gas up often, especially in the desert.
  • Have a flexible daily goal, not a rigid schedule.

If you tell me how long you’ve got and what you love most (nature, food, kitschy Americana, photography), I can sketch a custom Route 66 itinerary for you.

What’s your starting city and how many days are you thinking for the trip?