Selfguided Tour – Bike & Hotels
Eastern Route 66
from Grapevine, TX to Chicago, IL
On this section of the world-famous Route 66, you'll travel the original Route 66, also known as "America's Main Road" or "Mother Road." It's 1,700 km long and crosses two time zones and four states: Texas, Oklahoma, Kansas, Missouri, and ends in Illinois. Route 66 was and is the path of migrants, dreamers, rogues, and an entire generation of travelers discovering the vast West. The 1950s were a glorious time for Route 66, when thousands of cars drove bumper to bumper to experience the Western Frontier. Hotels, motels, gas stations, classic restaurants, and the "new" America were everywhere. Many Route 66 classics, such as gas stations, restaurants, and nostalgic landmarks, have survived. The famous and nostalgic Route 66 is a road seemingly built in heaven for motorcycle touring. Simply put, this is THE tour of tours in America.
GRAPEVINE – ARRIVAL
Days 1 & 2: Grapevine is a ten-minute drive from DFW/Dallas Airport. Grapevine's historic downtown is the starting point for your Route 66 Eastbound trip. Here you'll find numerous boutiques, galleries and artisan workshops, wineries, and restaurants. Must-sees include the Grapevine Vintage Railroad, a 1920s-era stagecoach depot (with daily round-trip service to Fort Worth), and Nash Farm, a late 19th-century working farm. Grapevine has evolved into a fun, Western-themed, shopping-oriented, and historic small town within the DFW Metroplex. From the Grapevine Observation Tower, 500 feet tall, you'll enjoy 360-degree views of the Dallas and Fort Worth skylines, DFW Airport, and beautiful Grapevine Lake.
GRAPEVINE – OKLAHOMA CITY
Day 3: Today you'll reach Oklahoma City, the third-largest city in the country, where you'll join Route 66 and visit the Oklahoma State Capitol, the only state capitol building with a working oil well. The city has so much to offer, including the First Americans Museum, the National Cowboy and Western Heritage Museum, the Oklahoma City National Memorial, River Sport Adventures, Stockyards City (home to the Cattlemen's Café and OKCOpry), as well as Bricktown, Midtown, Uptown, and the Paseo Arts District with fantastic food and plenty of entertainment. And be sure to try Oklahoma's signature dish: chicken fried steak. We'll be arriving in Oklahoma City via El Reno and the mile-long Pony Truss Bridge. 219 miles / 350 km away.
OKLAHOMA CITY – TULSA
Day 4: You leave OKC after a brief stop at the Oklahoma City Capitol. Then you drive the Mother Road, 100 miles through Indian Country in the Old West. The ribbon of asphalt that is Route 66 follows the landscape as if it has always been there. Along the way, you'll find attractions like the Seaba Gas Station in Warwick and the Red Barn in Arcadia, before arriving in the legendary city of Tulsa. Situated on the Arkansas River, Tulsa is a vibrant city known for its diverse neighborhoods, exceptional restaurants, and an unparalleled love of art, as well as one of the largest collections of Art Deco architecture in the USA. Overnight in Tulsa.
120 mi/ 192 km distance
TULSA- SPRINGFIELD, MO
Day 5: The next major city is Joplin. The old steel arch bridge over Rock Creek is on the itinerary, as is the blue whale in Catoosa. You'll visit the historic city of Miami and see the Route 66 Vintage Museum and the famous Coleman Theatre. US star Will Rogers regularly performed here. Attractions here include the Rainbow Bridge and the small town of Galena, which is almost at the border with the state of Missouri. Afterward, you'll visit the historic courthouse in Carthage and the old Sinclair gas station in Halltown. You'll pass through lesser-known towns like Conway and Lebanon, which lie along Missouri's Route 66. You'll spend your lunch break at an outdoor shopping paradise with a museum, the Bass Pro Shop, in Springfield, MO, where we'll also spend the night.
SPRINGFIELD, MO – ST.LOUIS
Day 6: The afternoon takes you through the hills of the Ozark Mountains, and you'll visit the Munger Moss Motel, famous from many Route 66 picture books. Another highlight of the day is the Devil's Elbow Bridge with its namesake biker bar. In the afternoon, the world's largest rocking chair and the Wagon Wheel Motel in Cuba are on the agenda. In the late afternoon, you'll reach St. Louis on the Mississippi River. The city's landmark is the gigantic arch, visible from afar. Overnight in St. Louis (215 mi/344 km).
ST.LOUIS – SPRINGFIELD, IL
Day 7: After breakfast, you'll cross the Old Men River as you leave the city and enter the state of Illinois. You might want to visit the Chain of Rocks Bridge there. There are too many towns along Route 66 to stop at every one, but the Paris Stop Cafe in Ariston and the Lady of the Highway statue in Waggoner are must-sees. In the early afternoon, you'll reach your overnight stop in Springfield, which is also the capital of Illinois. 97 mi/ 155 km
SPRINGFIELD, IL – CHICAGO
Day 8: Today, unfortunately, your tour comes to an end. But not before you see the last highlights of the old Route 66. The Capitol Building in Springfield is the first stop, followed by the Smiley Water Tower and the gigantic Hot Dog Man in Atlanta. Passing Funk's Groove and endless maple forests, you'll reach the Dixie Truck Stop. Along the way, you'll visit some old gas stations from the 1930s before reaching the Gemini Giant & Launch Pad Drive Inn in Willmington. From here, you'll continue along Route 66 past Countryside to Des Plaines. There, you'll return your bikes to our rental station. Overnight accommodation for the next two nights will be in the Chicago/O'Hare Airport area. Of course, an extension to Milwaukee and the Harley-Davidson factory is also possible – we'd be happy to advise you. (202 mi/323 km)
CHICAGO
Day 9: Today is yours to explore Chicago, also known as the "Windy City," at your leisure. Experience the city on a guided tour by double-decker bus and visit the Willis Tower (formerly the Sears Tower), where you'll have a fantastic panoramic view of the city from the Sky Deck. The Route 66 sign, Millennium Park, Navy Pier, Buckingham Fountain (featured in the opening credits of the TV series "Married... with Children"), and the iconic Bean are also on the itinerary (optional, advance booking required!). This evening, enjoy a meal at a nice restaurant and reflect on your tour. Overnight stay in the Chicago/O'Hare Airport area.
OUR TIP: Chicago City Tour
Dates
Daily departure.
Extension possible, no minimum number of participants! Individual trip planning. Flight not included (we would be happy to provide you with a quote at the current daily rate).
Included services:
- 9 nights as per itinerary in good standard or mid-range hotels or motels, some including breakfast.
- Rental of an HD Big Twin® including unlimited free miles, local taxes, preparation fees, half-shell helmets (subject to availability), saddlebags, security lock and motorcycle briefing.
- VIP supplementary insurance without deductible in case of damage or theft***
- Additional liability insurance for EUR 2 million
- One-way fee of $555 + tax
- detailed roadbook with extensive information and road maps
*** In case of theft/tire damage, the deductible is a maximum of US$2,000 or US$5,000 and must initially be paid by the customer. Following the tour, the claim will be submitted and the deductible reimbursed after review by our German reinsurer. INFO: Any recovery/towing costs are not covered and can be insured separately.
Services not included:
- Flight (we will be happy to make you an offer at the current daily price)
- additional transfers, personal expenses, parking fees, petrol, oil, entrance fees, road tolls, tips, other fees
- Travel insurance
Seasonal surcharges from:
- ."04-01-30.06.25
EUR 85. - p P. 2 people on a bike
EUR 170.00 p. P. 2 people on two bikes and single driver - ."08-01-30-09.25
‚ EUR 149% p. P. 2 people on a bike
‚ EUR 295, - p. P. 2 people on two bikes and single driver
Notes :
- The above prices are valid for the travel months of July and November to March (31.03.).
- For the E-Glide, Street Glide and Road Glide models, there is a surcharge of approximately 8.00-10.00 EUR per rental day
- Minimum age: 21 years
- A class 1 or A driving license is required.
- We recommend that you bring an International Driving Permit. However, this is only valid in conjunction with your national driving license.
- You will need a major credit card to pay the deposit.
- The transfer must be registered with EagleRider by telephone.
- The following Harley models are available upon request: HD Electra Glide, Road Glide, Street Glide, Heritage Softail, Low Rider
- Please note that no guarantee can be given (model guarantee can be booked from EUR 125,-)

