10 DAY – Route 66 Guided Motorcycle Tour

Self Drive Tours


Day 1 – Arrive in Chicago

We meet after lunchtime at the hotel. We also do an orientation with the bikes. Then we go out for dinner to discuss our big adventure!

Day 2 – Chicago to Springfield, Illinois –185 miles

Start Tour out of Chicago. Let’s go! We settle into our bikes, and aim for California. This is our first night on the road. See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.

Day 3 – Springfield, Illinois to Saint Louis 175 miles

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Lebanon, MO – 153 miles

Riding our motorcycles on Rt 66 through neat little towns, we have really fallen into synch with our Harley Davidsons. Americana. Devils Elbow is amazing.

Day 5 – Lebanon to Tulsa, OK – 233 miles

A great section of RT 66 with all the Googie Architecture. A really great motorcycle ride on old pavement of the Mother Road. We visit some great old diners. This is RT 66!

Day 6 – Tulsa to Clinton OK – 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles

Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner? Everything is bigger in Texas. Let’s live a little old Route 66 today on our motorcycle and tonight. You will know you are on old Rt 66 today. It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.

DAY 8 – Amarillo to Santa Fe, NM – 279 miles 

Cadillac Ranch is a Route 66 stop we must do. Who has ever spray painted a vintage Cadillac on Rt 66 before? Let me ask you again in the future… Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 on our Harley Davidson.

Day 9 – Santa Fe to Albuquerque

We start the day slow today. First have a leisurely breakfast in Santa Fe. Stroll around the town square, or take a ride up into the mountains. Next we ride the curvy hills to Maggie’s Diner in Madrid where the big showdown was in “Wild Hogs”. Plenty of time to soak in the unique town of Madrid and have lunch. There are also some other neat stops we have added in on the way to Old Town Albuquerque where you spend the afternoon exploring.

Day 10 – Albuquerque Departure Day