The Many Veils of The Mother Road

We shall not cease from exploration
And the end of all our exploring
Will be to arrive where we started
And know the place for the first time.

--T.S. Eliot, "Little Gidding," Four Quartets

You would think that the beginning of the most famous highway in America would be easy to find, but it's not. We are learning this the hard way as we drive around the Loop with Snyder's Route 66 Traveler's Guide and Roadside Companion in one hand and our atlas in the other, circling downtown in search of the definitive start. 

From its very outset, The Mother Road is shrouded with ambiguity.

If you’re looking for the original starting point when the highway was commissioned in 1926, that’s located at the “Historic Route Illinois US 66 END” sign on Jackson Boulevard, a few yards from the intersection at Michigan Avenue (formerly US 41). This sign marks the route’s original westbound alignment before Jackson Boulevard became an eastbound one-way west of Michigan Avenue in 1955.

If you’re looking for the official starting point, that’s two blocks east on two-way Jackson Drive at the entrance of Grant Park on Lake Shore Drive (currently US 41). The highway’s terminus, along with US 41, was moved to this location in 1933 when Jackson Boulevard was extended eastward onto land reclaimed for the Chicago World’s Fair.[i] There’s no sign here, just the lake itself marking the beginning and end of the road.

However, there’s also an unofficial starting point, as indicated on most maps, which is located at the “Historic Route Illinois US 66 BEGIN” sign on Adams Street, a few yards from the intersection at Michigan Avenue. Why “unofficial”? Route 66 never began on Adams and technically still doesn’t; The Route starts at the intersection of Jackson and US 41 and always has. 

But when Jackson became an eastbound one-way west of Michigan Avenue in 1955, the two-block section of Jackson east of Michigan Avenue remained a two-way street. Since then, Route 66 has made a half-block jog northbound on Michigan before continuing on one-way westbound Adams Street. 

Confused yet? Yeah, me too.

If you're not a stickler for historical details and want to save a lot of time, then bypass the two-block section on East Jackson Drive and the half-block jog on Michigan Avenue. Begin your westward journey with straightforward simplicity on Adams Street.

As you dodge traffic, chances are very likely that you won’t even notice the other unofficial starting point located at the end of the block on Adams, which is marked by a sign that reads “Illinois US 66 Historic Route Begins.” Supposedly, it's found near the staircase leading to the L platform, but we can't see it from the street.

After circling around downtown for the better part of an hour searching for a clear-cut beginning to Route 66, I have reached the conclusion that we probably won't find it. To resolve the ambiguity in my mind and temper T's frustration behind the wheel, I have decided to create my own starting point for our journey: the lakeshore. Since our trek will end at the Pacific Ocean, it seems fitting to begin our trip at Lake Michigan.

Turning left on Wabash, we circle around to Jackson Boulevard one more time and head back toward the lake. On East Jackson Drive, we cross Michigan Avenue and Columbus Drive, stopping at the light on Lake Shore. To our right is Buckingham Fountain, the lovely landmark for the official starting point of Route 66. Traffic is heavy on Lake Shore Drive, so crossing several lanes is difficult when the light changes.

Just down the road, we turn into the entrance of the Chicago Yacht Club at Monroe Harbor, the closest access to Lake Michigan from Grant Park. There’s no place to park, so we pull up to a yellow curb. I jump out of the car to look for a suitable place to conduct my kick-off ceremony. 

Lakefront Trail is busy with runners and walkers, so I have an audience for my sacred ritual. I place my ceremonial items on the concrete retaining wall: two small plastic bags, one holding tobacco and the other containing yellow cornmeal. Gulls are bobbing on the turquoise water of the placid lake; soft gray clouds blanket the sky. I offer a pinch of tobacco to each of the seven directions to open communication with the Divine, dropping the golden-brown strands into the water. 

I then offer pinches of cornmeal with gratitude to our Travel Angels, asking them to bless, guide, support, and protect us on our journey from the shore of Lake Michigan to the Pacific Ocean. The cornmeal forms a thin yellow sheen on the surface of the water. I bless the lake; I bless the ocean; I bless the elementals, plants, animals, and people that we will encounter along the way. I bless our vehicle and the route we will travel. I bless T; I bless our family; I bless myself. I offer blessing upon blessing until I feel the ceremony is complete. 

I'm now ready to begin our journey with a clearer sense of direction. No more circles.

From the lakeshore, we retrace our tracks through Grant Park on East Jackson Drive, and then turn right on Michigan Avenue, merging left into the steady stream of traffic. When we reach The Art Institute of Chicago a half block north, we turn left to head west on Adams Street. The “Historic Route Illinois US 66 BEGIN” sign appears on the left about 25 yards from the corner of Michigan Avenue. 

We have arrived where we started, and I am a bit wiser for all of our exploring, for I now know this place for the first time as one of multiple beginnings. T double parks so that I can jump out and snap some photos. 

While I pose for a selfie with my iPhone, someone with a lilting Australian accent asks,

“Would you like us to take your picture?” 

A couple in their thirties stands a few feet from the sign. She is holding a fancy digital camera; he flashes a friendly smile.

"No, thanks,” I reply. “I’m happy with my selfies, but I would be delighted to take your picture."

She hands me the camera, and I snap some photos of the couple in front of the sign, including one with the skyscrapers in the background rising into the clouds. When I return the camera, we start conversing. 

The couple is from Perth, Australia, and they have just finished driving Route 66 from Santa Monica. They have stopped here to commemorate the end of their weeks-long journey, which happens to be at the very same moment that I have paused at this spot to mark the beginning of ours. What synchronicity! 

I don't mention that the actual ending is on Jackson, and they don't remind me that the true beginning is on Jackson, too.

The woman's blazing blue eyes have seen many sights along the way, I’m sure, so I ask if they would like to share one of their peak experiences on The Route. Much to my surprise, their favorite part of the journey actually took place at home in Australia. They prepared for their adventure by watching videos together of Scottish comedian Billy Connolly, who had made a series of hysterically funny TV shows on driving Route 66—on a tricycle! They giggle as they describe a couple of their favorite episodes. 

A friend had also given them a helpful list of things to do and see, plus some places to avoid, on The Route. They don’t offer to share the list, maybe so they won’t spoil our adventure by influencing our choices. As our conversation concludes, they point to the other Route 66 sign at the end of the block, which they suggest I photograph, too. We bid each other farewell, and I jump back into the car.

We drive slowly to the end of the block and stop at the corner of Wabash. The sign is not visible from the street, so I get out and hail a man standing by the wrought-iron fence surrounding the stairway to the L.

“Hi there! Do you know where the Route 66 sign is?” I ask.

“Sure do. It’s right over there,” he says, pointing to a sign tucked away near the stairwell.

I thank him and take a few pictures of the sign, then turn around to greet him properly.

“My name is Clifford,” he says with a big, bright smile. “Glad to meet you.”

We strike up a conversation about Route 66. While we chat, I notice that his coffee cup is half full of coins and a few dollar bills. I tell him that we are just getting underway and point to the car where T waits patiently, double parked with emergency lights flashing, in the busy street. He is happy for us and offers a soulful benediction for our trip. I am so grateful for his blessing! I feel like my lakeside ceremony has manifested our first Travel Angel as Clifford, ambassador of the Route 66 sign on the corner of Adams and Wabash.

"May I take a picture of the two of us in front of the sign?" I ask. 

Clifford happily agrees, and the two of us pose with big smiles for a selfie.

Clifford the Travel Angel

"I love you," I tell him as I put a dollar in his paper cup.

"I love you, too," he replies. Our eyes meet in momentary communion.

I quickly return to the car, and we continue on our way. I can still feel the love.

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[i] Route 66 played a central role in the Century of Progress International Exhibition, the World’s Fair held in Chicago to celebrate the city’s centennial. As one of the nation’s principal east-west arteries, Route 66 was as much a symbol of progress as the “dream cars” exhibited at the fair by American automobile manufacturers: Cadillac’s V-16 limousine, Lincoln’s rear-engine “concept car,” the Pierce Silver Arrow, and the Packard V-12, which won best of show. By year’s end, Route 66 also became one of the few fully paved interstate highways in the United States, bringing more than 22 million visitors to Chicago by the time the World’s Fair closed on November 1, 1933.