Route 66 Harley-Davidson Exclusive VIP 10 Day Guided Tour

Guided Tour 10 Days / 9 Nights
Tour Map
  • 1620.0 mi = 2592.0 km
  • Summer, Spring, Fall
  • 55.0 - 105.0°F = 12.8 - 40.6°C

What could possibly be better than riding Route 66 on a Harley-Davidson? Well, how about kicking off your Route 66 guided tour with two nights in Milwaukee to enjoy a VIP experience at the Harley-Davidson Museum! This unique experience will be available to less than 50 riders per year, and only offered through EagleRider as the exclusive US provider of rentals and tours for Harley-Davidson Motor Company. You will spend two nights at the incredible Iron Horse Hotel right next to the Museum, you’ll see the actual size of the tiny shed where Mr. Harley and the Davidsons built their first motorcycles; all capped off by a one-of-a-kind Museum Experience. And if that’s not enough, you still have an incredible journey down The Main Street of America, Route 66, to look forward to. Route 66 in and of itself is the journey of a lifetime for most riders. Now, toss in a couple of days immersing yourself in the history, as well as the future, of Harley-Davidson, and you have the recipe for an unforgettable experience that will make you the envy of every rider on the planet.

Tour Itinerary

Welcome to Milwaukee, the birthplace of Harley-Davidson, and one of our favorite Great Lakes cities. We will help you with transfers from the airport to the Iron Horse Hotel in Downtown Milwaukee. Once everybody is settled, we will meet up with the rest of the group for a fun dinner and night out at one of our favorite local restaurants.
We will grab a great breakfast at Iron Horse before making the short van trip over to the H-D Museum for a truly VIP, behind the scenes experience. There is a lot to see in the Museum, so feel free to spend as much time as you like. It’s only a ten minute walk back to the hotel, where we will have a meetup planned for later that evening.
Today, we grab out Harleys and make the easy ride along the shores of Lake Michigan to the start of Route 66 in downtown Chicago. We will meet up with another EagleRider Route 66 group that is starting their journey in Chicago for a fun night out on the town, and maybe ribbing them a bit about how we just got to spend two days as VIPs in Milwaukee with Harley-Davidson! Tomorrow, we begin our journey down historic Route 66!
We’ll get a leisurely start to our day to give our Chicago riders a chance to grab their bikes from EagleRider. Once they are set, we will meet up with them and begin our epic journey, cutting through the state of Illinois before running all the way to the Pacific Coast. From Chicago you head south along the Pontiac Trail, the original name for this bit of the road here, passing through Joliet, checking out the Launching Pad Giant, stopping at the amazing RT 66 Museum in Pontiac and generally getting a feel for the rubber on the Mother Road.
Today we head towards St. Louis! We will stay primarily on the 2-lane sections of the Mother Road, traversing cornfields and small towns that represent the heartland of America. Our arrival into St. Louis will be over the Chain of Rocks Bridge, the original bridge where RT 66 crossed the Mississippi River. Enjoy the short ride today into the "Gateway to the West," St. Louis. This amazing city rests along the shores of the mighty Mississippi River and is home to some of the best live music and BBQ ribs in the country.
Try to get up early to walk across the street today and enjoy an early morning view of the St. Louis Arch and Mississippi River before we hit the road. We quickly leave the city in mirrors as we settle in to enjoy the rolling Missouri hills that make this area so beautiful and fun to ride in. We will stop and see the famous World’s Largest Rocking Chair in Fanning, wind our way on the twisting roads of Devil’s Elbow, and stop at other Route 66 icons. Tonight we will enjoy a stay in Joplin, a city that was hit very hard in 2011 by a massive tornado. Maybe tonight we'll hang with the locals and hear some amazing stories about what it was like to be in the eye of a massive tornado!
Today is all about the route! From Joplin we will head west through the hills and horse country through Oklahoma, crossing Miami, Claremore and Catoosa, home of the legendary Blue Whale before passing through Tulsa, We will also go through the reservations of several Native American tribes. In the 1830s, much of this land was considered "unusable" by the Federal Government, so various Indian tribes were "settled" there after colonization, including the Choctaw, Chickasaw, Seminole, Creek and Cherokee. This evening we will stay in Oklahoma City, the heart and soul of Route 66.! At night you can enjoy at Bricktown, the neighborhood in the heart of the city full of lively restaurants, bars and shops.
This morning we travel along some of the oldest stretches of Oklahoma’s Route 66. Once the land of vast buffalo herds, this section of 66 traverses some of the great cattle trails which were used in the 1860s to drive herds of cattle from Texas up to the railhead in Abilene, Kansas. We will ride along a section of the Chisholm Trial, which passes through Yukon and El Reno, and stop at the amazing Route 66 Museum in Clinton. After lunch we cross the border into the Texas Panhandle, the southernmost portion of the Great Plains. Once in Amarillo, our good friends from "The Big Texan Steakhouse" will pick our group up at the hotel in a fleet of old Caddies graced with the horns of Texas Longhorns across the hood and take us to enjoy the absolute best steaks in Texas
Today you leave Texas and are on your way into “The Land of Enchantment”, New Mexico. After passing through the world-famous Cadillac Ranch, we'll stop at the midway point of RT 66 in Adrian, Texas! And how about the ghost town of Glen Rio, where you can stand with one foot in New Mexico and the other one in Texas? From there we enter the land of the Comanche Indians, where mesas, mountains, cactus and pines define the landscape as we head up into the High Plains and altitude of Santa Fe in central New Mexico.
Today you will take a short ride to our EagleRider Albuquerque Location where you will return your motorcycles.We hope you enjoyed your EagleRider tour. Please be sure to let us know if you need an extra night or two in Santa Fe to enjoy the sights. See you next year! EagleRider.
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