Congratulations! After months of anticipation, the day to embark on this incredible journey has finally arrived. Take the shuttle or a taxi to your Chicago hotel and check in for the first night of your adventure. We’ll be in the hotel lobby to welcome you at 7pm and to inform you of our next days agenda for our trip to Milwaukee and the Harley Davidson Museum.

Chicago, IL– Milwaukee, WI

Our adventure begins in earnest today as we drive in the very comfortable Mercedes support van to Milwaukee. We’ll be back at our Chicago Hotel tomorrow night, so feel free to leave your large bags with the bell desk, & just take an overnight bag to Milwaukee. On arrival we’ll check into the exquisite Pfister Hotel. Your entrance ticket is included in the cost of your trip and you will have plenty of time to visit the hallowed ground of the Harley-Davidson motorcycle museum, & gain a fascinating insight into this iconic institution.

Milwaukee, WI – Chicago, IL

You’ll have free time this morning to re-visit the HD museum if you want to, before heading back to Chicago around noon. Upon arrival, you’ll have time to relax or enjoy a walk along the river or Navy Pier, before meeting up with the remainder of your fellow riders who will be joining you on the Route 66 guided tour.

Day 1: Route 66 Arrival Day, Chicago IL

Congratulations. After months of anticipation the day to embark on on this incredible, 2,850 mile journey, has finally arrived. Take the shuttle or a Taxi to your Chicago hotel and check in for the first night of your adventure.

Day 2: Chicago

Free day to explore Chicago and visit the start and end points of Route 66! You can also visit the Willis Tower and step onto the glass platform (if you dare!).  You will complete the paperwork for your bike rental late afternoon at the hotel, ready for us to pick up the bikes tomorrow morning and start riding Route 66!

Day 3 Chicago, IL – Bloomington IL – 125 miles

Today we put rubber to the sacred pavement of Historic Route 66 for the first time. The 2850 miles of concrete, steel and the grandeur of Route 66 lie ahead. We’ll ride through Joliet, Illinois,  then stop to say `Hello’ to the Gemini Giant standing guard at the entrance to Wilmington and Route 66 West. After lunch at the Polka Dot diner, we’ll visit The Standard Oil gas station in Odell which is a reminder of the many refuelling points which stood along Route 66 in its heyday.  The exceptional Pontiac Route 66 Museum comes next where you will learn about Bob Waldmire who was an artist and spent his life travelling Route 66.

Day 4: Bloomington, IL – St Louis, MO – 187 miles

The excitement is just beginning today. As we enter St. Louis, Missouri, we immediately notice the magnificent Gateway Arch. The gleaming, stainless steel structure welcomes travelers heading from East to West. It lies along the banks of the Mississippi, and is an absolute engineering wonder. Take an elevator ride to the very top, where you’ll have a fabulous view of the city below. Be sure to try some frozen Ice Custard from Ted Drewes world famous stand, just like the pilgrims of yesteryear did as they drove west on the Mother Road.

Day 5: St Louis – Joplin MO – 308 miles

Today you’ll be amazed with the fabric of countryside and the scenery the Midwest has to offer. The roads out of Rolla are a riders dream. We begin to navigate the gentle winding roads that put us into the rhythm of the ride. We take our time to ride through the ‘Devil’s Elbow’ to view what once was the deepest road cut in Missouri. Soon we’ll get a taste of what the real Route 66 was like. You see, when Route 66 was in its heyday folks knew this was an opportunity to make a living selling all sorts of sundries, offering hospitality and lodging to weary travelers, and re filling their cars thirsty gas tanks every few hours. Many savvy businesses came up with all sorts of interesting ways to grab attention and get folks to stop and spend a little money while filling up. We will stop at the Gay Parita Sinclair Gas Station, which drew customers in by the hundreds.  We end our day in Joplin, MO. For a well deserved night’s sleep.

Day 6: Joplin, MO – Oklahoma City – 254 miles

We start our day with a visit to Galena where we’ll see some `Cars on the Route’ and then ride over the Rainbow Arch Bridge at Bush Creek.  Miami comes next with some Vintage Iron to sort though.  After lunch you will see the famous Blue Whale at Catoosa, where travellers visited to bathe in the pond in days gone by.   A great days riding for sure!

Day 7: Oklahoma City, OK – Amarillo, TX – 274 miles

After coffee at Lucille’s we visit the Route 66 Museum in Clinton.  This is one of the best museums along the route and has fascinating interactive exhibits.  There are several eating places to choose from in Elk city where we stop for lunch.  We’ll ‘Drop In’  at the oil town of Shamrock and the most iconic of all Conoco gas stations.  We’ll  then show you the way to Amarillo! Get ready for a steak “Texas Style”, like a 4 1/2 pounder! A visit to the Big Texan steakhouse will surely stretch your digestive system to its limits!

Day 8: Amarillo, TX – Santa Fe, NM – 296 miles

Today we make our way into the heart of the Western United States and one of her most beautiful cities, Santa Fe, New Mexico. This quaint mountain town is nestled high in the Sangre de Cristo, or Blood of Christ, mountain range, which are thought to have been names for the deep red hues of the mountains during some sunrises and sunsets. Santa Fe is rich in Spanish and Native American history and culture, a unique blend that is reflected in the local art, architecture and cuisine.  You can’t spend more than just a few minutes walking the narrow streets of Santa Fe before you fall in love with this city and her people.

Day 9: Santa Fe

Today is a free day in Santa Fe. Relax in the hotel spa, enjoy the many fine art galleries, or just explore the heart of Santa Fe. The local native Indians are offering their superior craftsmanship products throughout the market square, & their handmade jewellery is particularly good. Don’t forget to try the Green Chilli Stew that has become a favourite of locals and visitors alike. The gastronomic selections increase here in Santa Fe. If you have been waiting for a fine culinary break Santa Fe offers it. If you feel like a ride today we can organize a day trip into the fresh mountain air of northern Arizona and southern Colorado. The trip north to Taos is stunning. The scenery changes as one heads north, & it’s hard to miss the great northern Arizona grandeur. One could spend a week here exploring the corner regions.

Day 10: Santa Fe, NM – Gallup, NM – 211 miles

Wild Hog or Del Fuego?  The choice is yours as we ride into intriguing Madrid this morning, the setting for the comedy film ‘Wild Hogs’. Be sure to call in at ‘Maggies’ for your souvenir T-shirt!  Lunch is a real treat at the Route 66 Diner One in Albuquerque.  New Mexico describes itself as ‘The Land of Enchantment’, and our riding today will confirm this. Look out for the beautiful and simplistic adobe architecture you’ll see along the way.

Day 11: Gallup, NM – Grand Canyon, AZ – 309 miles

It seems that our ride is just getting better and better each day. Soon we’ll cross into the Petrified Forest National Park where we’ll stop by and watch a short video explaining the unique beauty of the area, with miles of petrified logs, rocks, and artefacts. Did you ever imagine that you’d actually be ‘Standin’ on the corner in Winslow, Arizona’ as made famous by The Eagles in their song ‘Take it Easy’? You will today! We’ll take a diversion from Route 66 to the biggest hole in the ground you ever did see! It’s hard to explain just how big and marvellous the Grand Canyon is. No picture truly captures the grandeur and enormous size of this natural wonder.

Day 12: Grand Canyon, AZ – Kingman, AZ- 182 miles

Today’s riding is outstanding! Seligman, AZ is a town where the Spirit of Route 66 is alive and kicking and we’ll take advantage of a very famous BBQ/Steakhouse cafe for our lunch. Heading west along old Route 66 we get a real feel for what the mid west emigrants had to endure on their long trek to the promised lands of California. Our final stop for the day is in the famous Route 66 town of Kingman, situated in the Hualapai Valley between the Cerbat and Hualapai mountain ranges.

Day 13: Kingman, AZ – Las Vegas, NV – 185 miles

Leaving Kingman we head west through the quaint town of Oatman where mules are left free to roam the streets. Here you can get a real flavour of what the mining towns of the old west were like and you can take a jump into that past by visiting Oatman’s various shops and saloons. Las Vegas isn’t part of Route 66, but as we’re so close it seems madness not to visit this “Disneyland’ for adults!”.  See a show, have a flutter, or just enjoy the atmosphere of this crazy town where each hotel on the famous Strip vies for your attention by being more outrageous than the last.

Day 14 : Las Vegas

Free day to explore Vegas and take in the sights. Perhaps try your luck on the tables, or see a show at Caesars Palace!  And you will have time to fit in a Helicopter flight to see the Grand Canyon from the skies, or even land there depending on your choice of tour!

Day 15: Las Vegas, NV – Big Bear Lake, CA – 269 miles

The Mojave Desert offers stillness and interesting colours that only a few riders ever explore.  Just settle back into your seat and enjoy the ride. We head south from Las Vegas and into the Mojave National Preserve. This is California Desert riding and we will pass many old railroad sites and towns and we will see many of the unusual Joshua trees that the area is known for. Rejoining Route 66 we then head for Barstow before once again heading south to our overnight stay in the San Bernadino National Forest at the resort of Big Bear Lake.

Day 16: Big Bear Lake, CA – Los Angeles, CA – 168 miles

We are almost there now. With some of the best riding of the whole tour today we’ll take in the Crestline Highway and the amazing ‘Rim of the World’ before lunching at Newcomb’s Ranch.  Our ride then takes us on through the suburbs of Los Angeles and down to Santa Monica Pier where we’ll visit the plaque that announces that you have arrived at our final destination. After we linger and admire this sight we’ll grudgingly take our trusty bikes back to EagleRider. Tonight we’ll celebrate our fantastic journey and achievement over a beer or two. It’s the last night of the ride, but the beginning of a long friendship and many stories.

Day 17: Los Angeles, CA Departure

We have given you something that you never will forget; an incredible ride through the famous Route 66 with new friends, on the bike of your dreams. Thank you for joining us, we’ll miss you, and we hope we can arrange for another adventure with you in the future.

Autumn special Route 66 guided motorcycle tours prices: