The sign at the intersection of Adams Street and Michigan Avenue in downtown Chicago that reads “Illinois US 66: Historic Route Begins” is small, unremarkable, and arguably an unworthy trumpeting of the road that is ahead. Indeed, not a single office drone pays it any mind on this gloomy fall morning as they rush from the city’s lumbering El trains to their designated steel and glass towers for the day. Nevertheless, Ryan and I stand in front of it with beaming smiles and angle our iPhones just right so that we can snap a selfie that will surely be the envy of all.

This is day one of an eight-day, turn-by-turn journey that will cover all 2,448 iconic miles of Route 66, the most famous highway in the United States. It was designated in 1926 and made famous by westward thrill seekers, Dust Bowl migrants, and the oft-covered song of the same name. During its six-decade span it was realigned several times, decommissioned in 1985 in favor of the Interstate Highway System, and brought back to life more recently by road trip enthusiasts, municipalities looking to bolster tourism, and folks wistful of a vanishing America.

Although the road is book ended by Chicago and Los Angeles and winds through the heart of several cities including St. Louis, Oklahoma City, and Albuquerque, the highway is really a journey through numerous small towns to countless to name, some of which have survived and even thrived, off Route 66 nostalgia, and others which have all but rotted. To cross the country via interstate highway is to merely skim the continent, but to do it via painstakingly slow Route 66 is to discover an America that is undeniably friendly, often kitschy, and ultimately vanishing rapidly.

Our faithful companion for the journey is a 2015 canary-yellow Ford Mustang convertible. Thanks to her elaborate engineering, she requires no turn key in her ignition and is so badass in her numerous bells and whistles that we affectionately name her Carol, after the resilient, take-no-prisoners survivor of the zombie apocalypse in AMC’s The Walking Dead. We love this car.

Savoring the Windy City leg of the journey really means admiring the route’s literal starting point on Michigan Avenue where a 360-degree survey of the intersection puts road trippers in close proximity to Anish Kapoor’s much-photographed steel-sculpture Cloud Gate, aka “the Bean,” majestic Buckingham Fountain, and the newly revitalized Chicago Athletic Association Hotel thats current incarnation as a boutique hotel, carefully refurbished to pay homage to its roots as a turn-of-the-century men’s club, aligns perfectly with the legacy of Route 66 and is thus an ideal hotel for travelers seeking a starting point along the Mother Road.

Adams Street begins our westward journey cutting (what is for us as locals) a familiar path through the frenetic Loop, then crossing over the Chicago River, and onward to the city’s West Side. Route 66 signposts take us left onto Ogden Avenue and through Lawndale, a neighborhood which these days looks like it’s slouching. We see rail cars and power plants, this is the guts of the city, but the murals along the avenue brighten the drive, and we’re happy to wave goodbye to our famously “big shouldered” hometown as it vanishes in the rearview mirror.

Soon our eyes take notice of pretty Berwyn whose wide streets, Chicago-style bungalows (the most in the nation), and flashes of mid- century signage point to the Americana which lies ahead. We’re barely outside the city and already a USA that “once was” is looming large before us. Meanwhile there is Joliet, which, like many industrial cities, hints at former greatness but now feels like a drag on the American Dream. The rest of Chicagoland rushes by as 66 merges with I-55, but a slower pace soon returns as the road veers south and into small town America, the real beginning to our adventure.

Part of the thrill of driving Route 66 is that it is lined with superlatives such as “largest,” “biggest,” “longest,” “oldest,” etc., and in this regard Illinois does not disappoint. In Wilmington, for example, there is the Gemini Giant, a historic landmark in the form of a luminous 30-foot-tall “Muffler Man” astronaut who stepped out of the Atomic Age to serve as an advertisement for a now-defunct restaurant. There is also the giant Paul Bunyan “Muffler Man” statue in Atlanta, a sliver of a hamlet with a tiny, but winsome downtown. In nearby Pontiac, a series of pretty Route 66 murals cover most downtown buildings. Here we spot a cute gay bear strutting down the street in a shirt and jeans and think to ourselves, we could get used to small-town America.

Springfield, one of three state capitals we visit during our journey, yields a bounty of Abraham Lincoln related attractions including the stately residence he called home from 1844 until 1861 when he took office to become the 16th President of the United States. It’s right along the route, and so is the gimmicky Cozy Dog Drive In, a 66 icon and so-called home of the original corn dog. We have no idea if this claim is actually true, but neither of us has ever said no to putting a tasty wiener in our mouths, so we happily indulge. Illinois fatigue begins to set in, but not before the road brings us to Collinsville where we offer a round of applause to the town’s 170-foot water tower atop which stands the World’s Largest Catsup Bottle. Onward to Missouri.

I’ve always had a soft spot for St. Louis; I lived there briefly as a child. Its Gateway Arch is as stunning a monument as any, especially at dusk when its horseshoe shape beams against the melting sun. The city is just big and cosmopolitan enough to serve as an ideal day one stopping point. Unfortunately, St. Louis has all but bulldozed over all remnants of Route 66, a dilemma for strict Mother Road purists like us, but we do grant a reluctant seal of approval to the Magnolia Hotel, a landmark downtown building thats close proximity to the actual route and origins back to 1924, which officially qualifies it as a place worthy of resting for one night.

The bearded bartender at Central Table, a West End eatery set in a loft- ed warehouse, is what Ryan and I call a “crossover” guy in that he’s just distinguished and bearded enough to satisfy Ryan’s taste in men while being svelte and hipster enough to satiate mine. Meanwhile, we tease the gayness right out of our own adorable server Kevin who recounts the gay bar he visited in Chicago that made him take his shirt off (against his wishes) as part of its dress code. Kevin disappoints us by sharing intel that our cute mixologist is chatting with his steady girlfriend.

Later that night, under the overlapping paths of St. Louie’s intersect- ing freeway system and a billboard of a busty blonde dubiously pro- claiming “I love Chuck’s Boots,” we decide to take advantage of the moderate late-autumn temps and do some alfresco imbibing among the smokers at JJ’s Clubhouse and Bar. It is here that an uninvited plus- sized gal in a deep V-neck tee plops herself down awkwardly next to us and says, “I don’t have a penis, but I love you guys.”

She goes by Mama Bear, a name that makes Ryan and I bristle since our own nicknames are Papa Bear and Big Daddy respectively, and she’s apparently here to play the role of Cupid, although which of her friends she’s trying to set us up with she never does say. What she does do, however, is wedge herself firmly into our night dropping pithy one-liners like, “Santa Fe is for bitches,” and shoulder dancing to the Eurythmics “Sweet Dreams (Are Made of This)” which produces large beads of sweat around her face and cleavage.

In the morning we do find Route 66 nostalgia at Donut Drive-In, a 24-hour bakery that is a St. Louis institution including long lines that point to its worth. Day two is full of highlights beginning with a guided tour of Meramec Caverns, a 4.6-mile cavern system in the Ozarks. Our docent is Jeremy, a pear-shaped oddball with matted bangs and a cackle that is like a cross between a hyena and the Wicked Witch of the West and who offers random non- sequiturs like, “Get ready to meet your maker!” and “I’d hate to have you fall on your butt without placing your face in mine!” His tour is the kind of kitsch we are craving and makes us love this road even more.

Part of our Route 66 regimen is to ensure that both lodgings and restaurants are as strictly “mom and pop” as possible and this brings us to Shelly’s Route 66 Café, a threadbare charmer in teeny Cuba thats menu items are each named after cars. We build our own sandwich by asking our server to take their spicy breaded chicken and top it with chorizo, pepper jack, and jalepeño (a winning combination). The staff is so visibly excited by this discovery that they insist they’ll not only add it to the menu but also name it the Mustang Chicken Sandwich after our set of wheels. If you see it on the menu on your own Route 66 adventure all we can say is, you’re welcome.