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

Updated April 5, 20261 min read

1 answer · 0 votes

Avy Kennedydefinitive guideRoute 66

Answer

From Avy Kennedy

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

Here’s my definitive Route 66 game plan:

  1. Pick your direction: I like Chicago → Santa Monica so the scenery gets wilder as you go. Plan at least 10–14 days.
  2. Must-see highlights:
    1. Chicago, IL – classic start sign, deep dish
    2. St. Louis, MO – Gateway Arch
    3. Oklahoma small towns – pure vintage 66 vibes
    4. Cadillac Ranch, TX
    5. Santa Fe + Albuquerque, NM
    6. Petrified Forest & Winslow, AZ (“Standin’ on the Corner”)
    7. Kingman, Seligman, and quirky roadside stops in AZ
    8. Santa Monica Pier, CA – emotional finish line
  3. Stay & eat: Mix old-school motels, diners, and 1–2 “treat yourself” hotels. Always say yes to local mom-and-pop spots.
  4. Practical tips:
    1. Avoid rushing; some of the best bits are unplanned stops.
    2. Download offline maps; some stretches have spotty service.
    3. Gas up often, especially in the desert.
    4. 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?

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