Inspiring • Authentic • Tailor-Made

Inspiring • Authentic • Tailor-Made

Pettitts Travel UK 01892 515966

The Biggest Kicks on Route 66

Author: Lauren Curd

Route 66 or 'Main Street of America' as it is often fondly referred to as, is the most iconic road trip in the USA. It is a holiday featured highly on many people’s bucket lists, purely due to the kudos created by programmes such as Billy Connolly’s Route 66, Thelma and Louise, Cars and The Grapes of Wrath. However, we often get asked 'What is there to actually do and see when on Route 66 holidays?' so if you are wondering what to do with your time in each of the famed locations, read on and be inspired!


  • Millennium Park in Chicago is 25 acres of landscaped gardens with art and music and many concerts/events taking place throughout the year. Here you can visit 'The Bean' and take a picture of Cloud Gate
  • Historic Navy Pier - amusement rides including a giant Ferris wheel, Chicago Children's Museum, IMAX theatre, boat cruises, Chicago Shakespeare Theatre plus great places to eat and drink
  • The entrance to Grant Park is where Route 66 300 acres of green space separating the downtown area from Lake Michigan, see the Buckingham Fountain and the Art Institute of Chicago
  • The Magnificent Mile - a history-packed part of Michigan Avenue that rivals New York for shopping
  • Clubs - Chicago boasts an abundance of Jazz Clubs and Comedy Clubs


  • Hall of Fame in Pontiac
  • Henry's Rabbit Ranch in Staunton
  • Funks Grove in Shirley - home to the best maple syrup!
  • Behind what was the Riviera Roadhouse Restaurant in Gardner Illinois (unfortunately burnt down in 2010) is an old diner cart which has been restored by the National Route 66 Org. and is free to visit


  • Stand under the iconic Gateway Arch in St Louis
  • Ted Drewes in St Louis where you’ll find the best frozen custard and has been a Route 66 icon for decades
  • Route 66 State Park
  • Merimac Caverns in Stanton
  • Devil’s Elbow route is a very pretty drive
  • Springfield Missouri is full of Route 66 memorabilia


  • Some of the old brick road of Route 66 is on the lands of Oklahoma
  • Blue Whale roadside attraction in Catoosa – an iconic Route 66 attraction
  • The world’s largest totem pole can be found at Ed Galloway’s Totem Pole Park in Foyil
  • Route 66 Museum in Yukon (Garth Brook’s home town)
  • Route 66 Museum in Clinton, filled with vintage cars and an indoor “drive-in” cinema
  • Round Barn in Arcadia
  • Route 66 Museum in El Reno
  • National Route 66 Museum in Elk City
  • Milk Bottle Grocery in Oklahoma City – a giant milk bottle sits on the roof of this building that sells Vietnamese snacks and iced coffee


  • U-Drop Inn is the iconic green petrol station and restaurant in Shamrock which served travellers until the mid 90s and is now a tourist office
  • Cadillac Ranch in Amarillo, where you can spray paint Cadillacs with their noses in the desert
  • The ghost town of Glenrio – fantastic for Old West photos

New Mexico

  • Part of New Mexico have unpaved Route 66 which you can still drive on (be careful with your vehicle insurance if driving on unmade roads)
  • Ruts and marks from the old wagon trains can still be seen on this part of the route
  • Great shopping in Gallup
  • El Rancho Hotel in Gallup has had many film stars stay and is classic Route 66
  • Explore Santa Fe’s adobe-style architecture
  • The Tee Pee Curios shop in Tucumcari


  • Route 66 is really well preserved in Arizona and is some of the best driving – very twisty and sometimes precariously close to the edge of mountains
  • The most photographed part of the Route 66 including Petrified Forest, Painted Desert, Meteor Crater and Seligman, a small town completely engulfed by Route 66 with lots of whimsical themed shops
  • Sleep in a ‘teepee’ on Route 66 at the Wigwam Motel in Holbrook
  • Take a side trip off of Route 66 to visit the mighty Grand Canyon, which we often add in to our tailor made Route 66 holidays as an extra stop after Holbrook or Flagstaff, before continuing on to Las Vegas


  • Although not officially on the Route 66, most travellers wish to include the bright lights of Las Vegas within their road trip before heading on to Los Angeles
  • Stroll along the famous ‘Strip’, try your luck in world-class casinos or catch your favourite singer performing live on stage


  • Explore the wilderness area of Joshua Trees National Park en route to Los Angeles
  • Visit the Route 66 Museum in Victorville
  • Cruise along the final stretch of Route 66 before it turns into Sunset Boulevard opposite the Pacific Ocean in Santa Monica
  • Enjoy some fun on Santa Monica Pier


**This blog post was previously published on Medway Leisure Travel, now trading as Pettitts Travel**

Holiday Suggestions

Keep In Touch With Pettitts Travel

Sign up for our weekly travel ideas by email, keeping you up to date and inspiring you with ideas, information and suggestions for your next holiday.

Sign Up

Follow Us

Contact Us

Contact Us

01892 515 966

Speak to one of our Travel Consultants (* fields are required)

I would like to receive news and special offers