In June of 2019, my dad and I took a 14 day road trip on historic Route 66 from Santa Monica, CA to Chicago, IL. On the drive, we tried to stop as much as we possibly could to see all of the attractions, historic points of interest and small towns we passed along the way. Our goal was to document these spots so that others could see what Route 66 was like and also to encourage them to drive this historic route. If you are interested, you can see all of the Route 66 videos on my YouTube or read about each day of the drive by clicking below. Let me know what you think of Route 66 in the comments.

Day 1: Santa Monica, CA to San Bernardino, CA

  • Around 85 miles of driving
  • Highlights: Santa Monica Pier, Chicken Boy Statue, Fair Oaks Pharmacy, Colorado Street Bridge, Donut Man, Cucamonga Service Station, Wigwam Motel
  • Read more about Day 1

Route 66 Day 2: San Bernardino, CA to Kingman, AZ

  • 280 miles of driving
  • Highlights: Original McDonald’s Museum, Bottletree Ranch, Amboy, Oatman, Cold Springs
  • Read more about Day 2

Route 66 Day 3: Kingman, AZ to Flagstaff, AZ

  • 160 miles of driving
  • Highlights: Kingman Powerhouse Museum, Hackberry General Store, Grand Caverns, Seligman, Museum Club, Hotel Monte Vista
  • Read more about Day 3

Route 66 Day 4: Flagstaff, AZ to Gallup, NM

  • 190 miles of driving
  • Highlights: Twin Arrows, Standing on the Corner Park, Jack Rabbit Trading Post, Wigwam Motel, Petrified Forest National Park, El Rancho Motel,
  • Read more about Day 4

Route 66 Day 5: Gallup, NM to Santa Rosa, NM

  • 260 miles of driving
  • Highlights: Continental Divide, Grants Mining Museum, Rio Puerco Bridge, Rattlesnake Museum, Dog House, Blue Hole
  • Read more about Day 5

Route 66 Day 6: Santa Rosa, NM to Amarillo, TX

  • 180 miles of driving
  • Highlights: Tucumcari Route 66 Museum, Blue Swallow Motel, Midpoint Cafe, Cadillac Ranch, Big Texan
  • Read more about Day 6

Route 66 Day 7: Amarillo, TX to Oklahoma City, OK

  • 260 miles of driving
  • Highlights: VW Slug Bug Ranch, Leaning Tower of Texas, Devil’s Rope Museum, U Drop-In Cafe, Sand Hill Curiosity Shop, Route 66 Museum
  • Read more about Day 7

Route 66 Day 8: Oklahoma City, OK to Tulsa, OK

  • 120 miles of driving
  • Highlights: Milk Bottle Building, Pops Soda Ranch, Arcadia Round Barn, Seaba Station Motorcycle Museum, Cyrus Avery Centennial Plaza, Meadow Gold Sign, Buck Atom Space Cowboy
  • Read more about Day 8

Route 66 Day 9: Tulsa, OK to Carthage, MO

  • 140 miles of driving
  • Highlights: Blue Whale of Catoosa, Will Rodgers Museum, Ed Galloways Totem Pole Park, Cars on the Route
  • Read more about Day 9

Route 66 Day 10: Carthage, MO to Springfield, MO

  • 75 miles of driving
  • Highlights: Jasper County Courthouse, Gary’s Gay Parita Sinclair Station, Fantastic Caverns
  • Read more about Day 10

Route 66 Day 11: Springfield, MO to St Louis, MO

  • 250 miles of driving
  • Highlights: Munger Moss Motel, Uranus, World’s Second Largest Rocking Chair, Meramec Caverns
  • Read more about Day 11

Route 66 Day 12: St Louis, MO to Bloomington, IL

  • 165 miles of driving
  • Highlights: Ted Drewes, St Louis Arch, Hare it is, Cozy Dog Drive In, Muffler Man
  • Read more about Day 12

Route 66 Day 13 – 14: Bloomington, IL to Chicago, IL


If you want to watch our entire Route 66 journey, you can see the full trip in the below video playlist.

Hopefully you enjoyed this trip down Route 66. Let me know what your favorite spot is on the drive in the comments, or if you have any questions we can answer.