The beginning of the Historic Route 66 currently starts at the Art Institute of Chicago, on the corner of South Michigan Avenue and East Adams Street. The original road began at Jackson Boulevard and Jackson Avenue and moved several times before the route was officially decommissioned.
One of the first stops along the route out of Chicago is Dell Rhea's Chicken Basket, which opened in 1946. In the beginning, the restaurant's famous fried chicken was served in a basket with a few sides. The restaurant attracted national attention in 2009 via a Food Network episode of Guy Fieri's "Diners, Drive-Ins and Dives."
Continuing southwest, travelers historically stopped to fill gas tanks and grab snacks at Ambler's Texaco Station in Dwight, Illinois. Opened in 1933, Ambler's was the oldest surviving gas station on Route 66 until it closed in 1999—it's since been reopened and serves as Dwight's welcome center.
The Funk family in Shirley, Illinois, has been tapping maple trees and making Funk's Grove Pure Maple Sirup—yes, it's spelled correctly—since 1824. When Route 66 was established in 1926 it passed by the family farm, bringing a steady stream of visitors to purchase the deliciously sweet products. Road trippers can still purchase maple syrup at the Funk's Grove Store.
The Chain of Rocks Bridge crosses the Mississippi River from Madison, Illinois, to St. Louis and quite distinctively makes a 30-degree turn halfway across the river. The bend made the bridge safer for river boats and, because of the incredibly rocky river bottom in that section of river, put the bridge on sturdier ground to support the weight of the piers. A new Chain of Rocks Bridge was built in 1967 to accommodate Interstate 270 so the original bridge now serves a more leisurely purpose connecting bike trails on both sides of the river.
You know you've arrived in St. Louis when you see the Gateway Arch. The monument was built in 1935 to commemorate westward expansion of the United States and at 630 feet, the country's tallest monument is hard to miss traveling along the route. The top of the arch offers views for more than 30 miles on a clear day.
Weary travelers can still find rest at the oldest continuously operated motel on the route—Wagon Wheel Motel in Cuba, Missouri. For an extra peek at Americana, ask for Room 16. It still has a "Magic Fingers" coin-operated, vibrating bed.
The Devil's Elbow in Missouri was named for a sharp bend in the Big Piney River that frequently stalled lumberjacks trying to float logs downstream. Despite its sinister name, it's been called one of the prettiest places along Route 66. The town hearkens back to the highway's heyday with quaint shops and restaurants. The old truss bridge dates back to 1926.
As you pass Cars on the Route in Galena, Kansas, make sure to point out Tow Tater to the kids. The 1951 International Boom truck was the inspiration for the loveable "Mater" in the Pixar movie "Cars." The former gas station plays up its connection to the movie, and also offers travelers sandwiches, snacks, antiques, "Cars" memorabilia and local artwork.
In the early 1970s, Hugh Davis built the Blue Whale in his pond in Catoosa, Oklahoma. Family and friends already used the pond as a swimming hole, but the addition of the blue whale brought more people wanting to dive from its tail and the Davis family opened it to the public. Even overheated travelers along the route would stop for a dip. It's no longer open for swimming, but it has become one of Route 66's most recognizable roadside landmarks.
Lucille's Roadhouse is based on the original Lucille's restaurant located a few miles down Route 66 in Hydro, Oklahoma. This 1950s-themed diner has vintage gas pumps out front and is bedecked in chrome, glass bricks and colored lights. Hungry ramblers can fill up on chicken-fried steak, hearty burgers or—if it's early enough in the day—an all-you-can-eat Route 66 breakfast.
The Tower Station and U-Drop Inn in Shamrock, Texas, was originally a service station and cafe. Legend has it it's unique design was first scratched into the dirt with a nail. With light pink exterior and neon lights, it is a shining example of architecture during the Mother Road's heyday. Visitor can still drop in but now it's a visitor center, chamber of commerce and community center.
A newer icon of the famous road trip is the Cadillac Ranch in Amarillo, Texas. In 1974, 10 Cadillacs were buried nose down as an art installation created by the art group Ant Farm. The paint schemes are ever-changing, as graffiti artists—and perhaps Route 66 travelers—continually leave their marks.
All that traveling can make you hungry. Hungry enough to eat a 72-ounce steak with all the accoutrements? If so, stop at the Big Texan Steak Ranch while passing through Amarillo, Texas. The meal is free for anyone who can polish off the enormous steak, a salad, baked potato, shrimp cocktail and a roll in less than an hour. Patrons of all appetites are welcome to browse historic Route 66 memorabilia in the gift shops.
To really experience the Route 66 of the 1950s, check into the Blue Swallow Motel in Tucumcari, New Mexico, with rooms that boast period furniture and vintage lighting. It's one of the few motels remaining that have garages next to the rooms and several feature murals from "Cars" painted on them.
Route 66 passes through the heart of Laguna Pueblo in New Mexico. Buildings are made of stone and adobe, and the people here have been here since at least 3000 A.D., although the village was established in 1699 after the Pueblo Revolt. Stop to learn about the history of the area and purchase local crafts and pottery.
Petrified Forest National Park and the Painted Desert in Arizona are only one of the spectacular landscapes the Mother Road passes through. The desert gets its color from the layers of shale, siltstone and mudstone. The Petrified Forest features 222-million-year-old trees turned to stone and fossils found here include dinosaurs, freshwater snails and ferns. It's a great place explore while walking off the stiffness of a long car ride.
While traveling through Arizona, stop at the Skywalk, a newer Route 66 attraction in Peach Springs, Arizona. Opened in 2007, the attraction is part of Grand Canyon West Resort and offers a unique view of the natural wonder from 4,000 feet above the Colorado riverbed. The glass floor allows brave travelers to look straight down into the canyon.
Onward toward California, travelers can find a town that time forgot. Oatman, Arizona, has changed little since it's gold-mining days around the turn of the last century. It died out in the 1930s, leaving plank boardwalks and rustic but authentic buildings. Burros—wild donkeys—freely roam the streets looking for a snack. Catch a stagecoach ride with a local who will likely offer to sell you their handmade wares.
Another new attraction along Route 66 is Elmer's Bottle Tree Ranch in Oro Grande, California. In 2000, Elmer Long welded "branches" onto poles to hold colored glass bottles. The creation resembled Christmas trees, and now number more than 200 trees. The folk art installation is free to wander through and visitors are welcome, but be mindful that it is on Elmer Long's private property.
Weary travelers can sleep in a wigwam at Wigwam Village in San Bernardino, California. The location is the seventh of a chain of wigwam village hotels across the country but only three remain—in Kentucky, Arizona and California. The wigwams are teepee-shaped cabins resembling an Indian encampment, but feature all the modern amenities.
Route 66 ends at the pier on the Pacific Ocean in Santa Monica, California. For a little excitement, ride the Ferris wheel on the Santa Monica Pier, or take a stroll along the boardwalk.