My 1st Hitchhike + Stranger Love = Substack

Warning! This post contains:

one (1) pretty woman, one (1) cop, one (1) trucker – statistically impossible
a DUI: Dylan Under the Influence, and
hobohemian propaganda

Reader discretion is advised. So is a thumb.

Hitchhiking and Substack are fueled by the kindness of complete strangers. But they’re not strangers for long, are they? There’s a cathartic freedom in talking to someone who doesn’t know where you live. Social guardrails vanish. Secrets sneak out. Stories start to volley back and forth and then BAM! — you’re friends.

My first hitchhiking experience happened a few weeks after my wife, Melina, and I found out we were having twins.

I was driving from Nashville to Indianapolis to meet Mel at a Bob Dylan concert when I saw two hitchhikers standing next to the road.

“Hop in.”

I told the young women where I was going, but they didn’t care. They were riding the wind.

After some small talk, I had to get it off my chest. I hadn’t told anyone about the twins, so opening up to complete strangers was perfect. They talked me through some doubts that I wasn’t sure how to convey to family. I had always wanted to be a dad, but was afraid settling down meant sacrificing my dreams. Ever since I read Into The Wild, I wanted to march into the open country and live the hobohemian life. At least for a while.

Picking up a couple of free spirits was a spark, but their stories of adventure lit a fire under my ass. They urged me to take the leap — told me I could easily go on a short journey before the kids came.

My first hitchhike

Back in Nashville, I wrote an anthem to commemorate my trip called “Free Ride Lullabye.” I planned to unveil it after getting some actual street cred by hitching my way to the Frank Brown International Songwriters Festival. This was an annual pilgrimage to the Gulf Shores.

But I had always attended as a fan. This was my first year that I was a performing songwriter, so my plan had to get me there on time, or I risked burning bridges that had taken years to build. In particular, I had always dreamed of performing at the legendary Florabama, the biggest roadhouse in the South. No way could I let this crazy idea screw it up.

All the festival’s A-listers play the ‘Bama, but around midnight, folks start trickling across the street to the River House, where the real magic happens. All the stars live there during the festival and jam around the kitchen table, or shut the hell up and listen as one songwriter drops a tune that blows everyone away. The bombs drop all night until everyone is obliterated. That’s where I needed to be.

So on November 17, 2008, my journey began. Well, actually I cheated and got a ride to the highway. Melina wouldn’t take me on principle, meaning she didn’t want to play a role in some serial killer picking me up and selling my organs to China. Or something like that.

Since calling a taxi would be a terrible beginning to a story about hitchhiking, I decided to call our realtor. She found our Nashville home where we would eventually raise the twins.

“Hey Ja’nay-nay! Remember when you said to call anytime if I needed you? Well I was just checking the time and ‘anytime’ is right now.” She picked me up immediately — told me not to get killed before she dropped me off on Old Hickory Boulevard.

The temperature was close to freezing at sunset and dropping fast. I didn’t even make it off the 65 South entrance ramp before I got my first ride.

Leigh Ashby

She was young, attractive, had short blonde hair with a pretty smile, and the first thing she did was apologize.

“I’m sorry, but I can only take you to Concord.” I tilted my head back and laughed from my gut. Concord Road was only a few miles away. “Don’t worry darlin’. This is the first time I’ve ever hitchhiked and it only took me a minute to catch my first ride. It’s a good omen, and you’ll get me one exit closer to the beach.”

Her name was Leigh Ashby. She said she was new to Nashville; just moved from Winston-Salem. “That’s cool,” I said. “I have a friend named Mostafa who moved here from Winston-Salem. He studied film at the School of the Arts.”

She perked up, “MOSTAFA!? Crazy Moroccan dude with dreadlocks?”

Leigh parked on a side street and we traded stories about our mutual Moroccan. Before she left, she gave me a mix-CD that she had made especially for road trips. “I have friends who hitchhike,” she said. “So when I saw you, I just felt called to help out.” We parted on that thought.

I wasn’t having much luck on Concord Road, so I decided to try the highway. My best friend Buzz once told me to walk backwards so people could see your face. It made sense, but even a professional vagabond like Buzz would find it difficult to walk backwards while holding a guitar and pulling a cheap suitcase with chincy wheels. I couldn’t even stick my thumb out.

Out of necessity, I managed to push the guitar neck through the suitcase handle so it could ride on top. Freeing up one hand was great, but freeing up the thumb was an evolutionary triumph.

But none of it did me any good that night. By the time I could properly hitchhike, it was too dark and nobody could see my face. Right about the time my shoulders were starting to ache, someone pulled over. Finally! I couldn’t see anything through the headlights. As I walked up, the driver got out. This was a little odd. He had a funny little hat too.

“Dammit!”

He was a cop — told me it was illegal to walk along the highway if I was hitchhiking and said he’d give me a ticket if he saw me past the next exit.

It’s only two miles to Moores Ln, but by the time I got there my shoulders were in bad shape. I regretted not getting a gig bag with shoulder straps. Hell, I really didn’t need a guitar; there would be hundreds to choose from at the festival. Losing my guitar would have been a bad idea though. A guitar is like a beacon of light for hitchhikers. Drivers can see a gig bag sticking up from far away. Plus, people like to support starving musicians.

If I could do it again, I would ditch the guitar, but put all my clothes in the acoustic gig bag. That way, I could lose the suitcase and still give off good musician vibes.

The grueling walk along the highway was over, but all the expensive cars flying by at the exit made my situation look bleak. My thumb was merely a billboard protesting the status quo. Nobody cared. I wasn’t allowed on the highway and the BMWs in Brentwood weren’t stopping. The drivers didn’t even give me societal stink-eye. I didn’t even exist to them.

That’s when I realized that I had to look for shelter and prepare for a tough night. There were some bushes nearby that looked promising.

Officer Whitt

But just before I disappeared from polite society, another cop pulled up, rolled down his window, and asked for my license. He said someone had reported suspicious activity, and asked why I was loitering. I told him my purpose as he ran my ID.

“Son, did you know your license is expired?”

“No sir I didn’t. I guess it’s a good thing I decided to hitchhike.” He laughed, which made him sound human. “It’s a good thing,” he agreed. “You know I’m not supposed to do this, but you’re not going to catch a ride here. I can take you to the Love’s truck stop, about 10 miles south. You’ll have better luck down there.”

Buzz said you almost never get rides from pretty women, cops, and truckers. I was already two for three and the second anomaly was taking me to the third.

Once we got in, Officer Whitt was even friendlier. He asked about the festival, what type of music I liked to listen to and play. While we were talking, he flipped open his dashboard laptop and put on some background tunes.

“Have you heard Dylan’s latest album, Modern Times?”

“No, but a couple months ago, I saw him live in Indianapolis, and he played a few songs from it.”

“Cool, I just got it.”

As Officer Whitt scrolled through his iTunes library, the patrol car started veering to the left and right.

I got scared for a minute, until it hit me. In Cop Land, a four-lane highway is really just one big lane. Police don’t have dotted lines.

Nobody passes a cop. Officer Whitt wasn’t even looking at the road. Then the music drifted in. The steel guitar slid into my ears and her strings began to cry. We were floating. I wouldn’t have cared if Officer Whitt closed his eyes with me.

Then his Bobness laid it on us.

“In the still of the night, in the world’s ancient light.
Where wisdom grows up in strife.
My bewildered brain, tolls in vain
Through the darkness on the pathways of life.”

Maybe it was a sign of what modern times will look like one day; vagabonds and cops coexisting in peace.

Officer Whitt dropped me off at Love’s around 9:30 pm, wished me luck, and shook my hand as we said goodbye.

I called Melina immediately to tell her that I had just hitched a ride with a huge Dylaphile (or “Bob Cat” as she likes to put it). Mel’s the biggest Dylan fan I know; seen dozens of shows. Bob even said hi to her once between songs. I heard it on one of the bootleg recordings. It was sort of unprecedented for him to say anything at all, but sure enough, he stopped the show to make an announcement.

Ol’ Bobby D. said, “I’d like to say hi to the president of our territorial fan club down front, Miss Linda Lou. It looks like someone shuffled her away. I wish she’d come back.”

After hearing this, Melina ran back up to the front and Bob said, “Hey, you’re back!”

I told her, “If Bob sweeps you off your feet one day, be sure to ask him if I can tag along. Just give me a small room in the castle. He’s got a castle right?”

Melina was just happy I wasn’t freezing to death in a bush. Her sigh of relief said it all. She finally gave me her blessing.

Love’s Truck Stop

The temperature was in the mid-teens, so I got right to work: “Hey, I’m playing at a festival in Perdido Key and could really use a ride if you’re heading that way.” The truckers were all nice, but either they weren’t allowed or they weren’t going south. I delivered my pitch for a few hours before an older gentleman sounded halfway interested. “I’ll think about it.” To which I replied, “I’ll play for my ride or I’ll shut the hell up, either way’s cool.” The man smiled and said, “I’ll be right back.” After getting some provisions, he returned. “C’mon, hop in.”

I was three for three in hitchhiker anomalies! Then came the catch.

“I gotta warn you though, you’ll have to share your seat with another passenger.” I didn’t reply. “What kind of weird kinky trucker shit is this?” I thought. But I was so cold and desperate that I had to scope it out. We walked over to the truck. Dude opened the door and there, sitting on the passenger seat, was the cutest little black poodle I’d ever seen. We both started laughing as my new friend gave me a hearty pat on the back.

Casey Stengel

His name was Casey Stengel (also the name of a former New York Yankees manager) and then there was Ross, the dog. Casey told me how he’d saved Ross a few years back; said he was backing his truck up when someone shouted “Stop!” Casey got out and found this little pathetic creature lying down next to his tire. Ross was in a state of despair, with long hair like he’d been lost for months, all matted and tangled up with burrs. “It’s a good thing I didn’t roll over the poor thing. We’ve been best friends ever since.”

Ross sat on my lap the whole way and listened to us talk about life, the universe, and everything. Like me, Casey wanted to be free and see the open country. Trucking accomplished both. He’d been to every state and traveled three million miles with Ross by his side. Since Casey owned his rig, he could turn gigs down and vacation for as long as he wanted after a drop off. As we talked, trucking started to sound less like a stereotype and more like a romantic dream.

It was heavenly. The entire southern sky looked like fireflies high on cocaine. Later on, I found out that it was because the Leonid meteor showers were peaking. There were so many shooting stars. We lost track somewhere around seventy. Some of them had tails stretching clear across the horizon.

Time flashed by as well. Eight hours later, we were practically family. Casey took me all the way to Love’s in Mobile, Alabama, but wouldn’t let me go. He insisted on waiting until Buzz arrived to pick me up. As he opened his cooler and started making sandwiches, I got the guitar out and started fingerpicking the riff to my newest song. The least I could do was play for my ride.

🎶Free Ride Lullaby

No time to dream American Dreams
Gonna ride the wind and spread my wings
Can’t stand the man. Time to run
New vocation vagabond

I adore you babe, but I can’t tell
When to kiss and when to bail
I’m so sick and tired of
Broken hearts and chasin’ love

I threw away my telephone
Kept my thumb and some rollin’ bones
I threw away my piece of pie
For a piece of mind and a battle cry

No time to fear no lookin’ back
I found myself on the railroad tracks
I see my breath in the air
Catch a train go anywhere

The Gods are blowin’ in my hair
The world is whirlin’ I declare
I’m not homeless, I’m home-free
Nothin’ nobody can take from me

Free ride lullaby

While I played, Casey made me a killer club sandwich. He made a point of saying that he only gets fresh bread and organic produce. I felt bad for scarfing it down and not savoring the aged sourdough. While I was shoving food into my face, Casey asked if he could play a tune.

“Of course! Please.”

So he picked up my Takamine and started fiddling around. He was pretty rusty, but I could hear the skill buried beneath the years. I could tell that the guitar was a long lost friend. Then finally, Casey remembered the riff and started to sing “Suite: Judy Blue Eyes,” by Crosby, Stills and Nash. As he started to sing, Ross started to wag his little nub of a tail. Then halfway through the song, this big ol’ trucker-of-a man began to sob. He got so choked up that he stopped playing.

“You alright?” I asked.

“Yeah … no, I’m fine,” he said. “I just realized … this is the first time I’ve played for Ross.”

I’ll never forget their expressions. The little poodle was looking up at the big burly trucker, listening intently. Apparently, they were having a moment.

It was hard to keep my composure. Fortunately, Casey also sensed the hilarity and tears turned to laughter, which gave me permission to join in as Casey continued the song where he left off.

It was too much. A flood of emotions washed over me. I began laughing and crying. I didn’t know how to feel because I was feeling everything at once. At that moment, I suddenly became still.

The closest thing that captures the way I felt comes from the Sanskrit definition of nirvāna. It roughly translates to an “extinction or disappearance”; literally, “a blowing out.” That’s it. I’m pretty sure I had a blowout. Like a fire that ceases to draw breath and goes out, all my emotions vanished, and for a brief moment there was clarity and gratitude for the gift the universe had given.

When Buzz picked me up, it was still dark. By the time I finished telling my story, we were rolling along the Perdido Key coast as the sun was coming up.