Freedom Ride 250: Day Zero

The Ride Begins

For months, Freedom Ride 250 had existed mostly in my imagination.

It lived in notebooks filled with route plans, sponsor pitches, article ideas, gear lists, maps, and enough checklists to make an air traffic controller jealous. Every spare moment seemed to revolve around this project. I’d spent countless hours preparing—not just for a bicycle ride, but for a journey I hoped would celebrate America’s 250th birthday the best way I knew how: one mile at a time.

Now there was nothing left to plan.

Tomorrow was Memorial Day weekend, and I was flying to Washington, D.C., to begin riding across America.

You’d think after all that preparation I’d feel confident.

Instead, at two o’clock in the morning, I was wide awake.

Excitement? Absolutely.

Fear? Oh... there was plenty of that too.

What if the bike breaks down? What if I can’t handle camping night after night? What if I get hit by a distracted driver? What if somebody decides they don’t appreciate the patriotic message behind this ride? My imagination, which had spent months dreaming about incredible moments on the trail, had suddenly switched careers and become a full-time disaster consultant.

It wasn’t exactly the emotional sendoff I’d pictured.

I climbed out of bed—again—and opened my luggage for what had to be the tenth time that day.

Clothes? Check.

First-aid supplies? Check.

Bike repair kit? Check.

Camera gear? Check.

Extra batteries, cables, chargers, and enough miscellaneous equipment to outfit a small expedition? Unfortunately... also check.

Nothing had changed since the last time I’d looked.

I zipped the bags shut, shook my head at myself, crawled back into bed, and managed something that was closer to a nap than actual sleep.

A few hours later I was headed to the airport, because if there’s one thing I hate, it’s being late.

Ironically, being early didn’t matter.

While I’d been busy inventing fictional catastrophes and reorganizing my luggage for the hundredth time, I had completely ignored two things that actually mattered: the weather forecast and the emails from Delta.

Neither one was good news.

I arrived at the airport around 6:15 that morning only to discover my 7:30 flight had been delayed until 10:00.

Then 10:00 became 11:30.

So much for the carefully crafted plan.

The original idea had been simple: land in Washington early, pick up Lady Independence—my e-bike—from the bike shop where I’d shipped her, and be rolling onto the trail sometime around one or two that afternoon.

That plan evaporated while I sat at the departure gate.

Then I checked the weather.

Washington wasn’t just getting rain.

It was getting rain.

A severe weather watch covered the area, and forecasters were calling for days of steady storms. If I’d bothered to look before leaving home, I probably would have delayed the trip by a week. I’d ridden portions of the C&O Canal Towpath before. Nearly 200 miles of mud, puddles, and soaked gravel isn’t exactly where you want to begin a cross-country adventure.

But by then I was committed.

In my travel journal, I officially labeled this Amateur Move #1: Always check the weather before launching a major expedition.

The flight itself turned out to be uneventful. The roughest part wasn’t the turbulence—it was catching a few curious, and not-so-curious, looks from passengers who noticed the TPUSA Freedom T-shirt I was wearing.

It wasn’t a subtle shirt.

Neither was the mission behind this ride.

Freedom Ride 250 was always meant to be an unapologetic celebration of America, and I wasn’t about to hide that before the journey had even begun.

By the time I finally landed in Washington, it was nearly two in the afternoon. My carefully organized schedule was already in pieces, and the dark clouds gathering outside made it obvious I needed to adapt.

So before I ever turned a pedal, I made my first pivot.

Instead of heading straight for the trail, I booked a hotel for the night.

It wasn’t an expense I’d planned on, but between the delayed flight, the approaching storms, and the fact that my rain gear suddenly looked woefully inadequate, it was the right decision.

Sometimes the smartest adventure is knowing when not to start one.

After checking into the hotel, I made my way to Georgetown Pro Bike to reunite with Lady Independence.

Since she’s an e-bike—and a very heavy one—flying with her wasn’t really an option. Two weeks earlier I’d boxed her up and shipped her through BikeFlights, the service many cyclists use when transporting bikes across the country.

Overall, I liked the process. BikeFlights offers several box options, including one that only requires removing the front wheel and handlebars. Still, once everything was packed, I couldn’t shake the feeling that the box wasn’t nearly as sturdy as I wanted it to be.

At the UPS Store, I asked for extra tape to reinforce it.

Let’s just say the enthusiasm to help wasn’t exactly overflowing.

As it turned out, my concern had been justified.

When I arrived at the bike shop, they told me the box had shown up upside down, barely holding together despite all the extra tape I’d wrapped around it.

Worse, the bike had been damaged during shipping.

Thankfully, most of it was cosmetic—a few scrapes to the handlebars and rear rack—but the front fenders were completely destroyed.

On most rides that would be annoying.

On the muddy C&O Canal Towpath, where miles of crushed gravel quickly turn into flying mud, losing the front fender was a genuine problem.

It also meant another unexpected expense before the trip had even officially begun.

Still, this is exactly why I’d built a cushion into the budget.

Adventure rarely follows the script you’ve written.

So I inspected Indy, accepted the damage for what it was, paid for the Burley trailer I’d be towing behind the bike, and reminded myself of something I was about to learn over and over again during Freedom Ride 250.

The adventure had already started.

I just hadn’t turned the pedals yet.

Riding through the streets of Washington, D.C., while towing a trailer behind an e-bike turned out to be an adventure all by itself.

You’d think drivers in D.C. would barely notice another cyclist. The city is packed with people commuting by bike and delivering food on two wheels. Compared to many cities, cyclists are practically part of the traffic ecosystem.

Even so, I still collected a few unnecessary honks along the way.

Apparently, towing a trailer behind a heavily loaded patriotic e-bike attracts a little attention.

After making it back to the hotel, I had two priorities: food and better rain gear.

Fortunately—or unfortunately, depending on your bank account—I was in REI territory.

My relationship with REI has always been a complicated one. I genuinely love the store. They carry excellent brands, knowledgeable staff, and just about every piece of outdoor equipment you could imagine.

I just wish they didn’t charge as though every sleeping bag had been handcrafted by mountain monks. And then there is the bag policy.

Even though you are paying a pretty number of pennies for the products at REI, they still have a company policy of no bags…because of global warming or whatever. So, you have to carry your items out in your hand; like you are leaving a garage sale after paying Sotheby’s prices.

I made my way over to the clothing section and asked the salesperson to help me find a rain jacket.

She gave me the kind of smile that politely says, You don’t come to REI expecting bargains.

I started looking at jackets around the $99 sale price, figuring they would get the job done. She gently, I wish I could remember her name, she was great—but persistently—steered me toward a three-layer shell that cost nearly twice as much.

Every time I picked up the cheaper jacket, she’d explain another reason why the more expensive one would perform better.

Eventually she pulled out the final argument.

“It’s on sale.”

“And you’re a member. You get a 20% discount.”

Against my better financial judgment...

...I caved.

It ended up being one of the best decisions I made on the entire trip.

Over the next several days that jacket endured hours of steady rain, wind, and everything the weather could throw at me. The cheaper option probably would not have worked.

Sometimes paying a little more really is buying peace of mind.

With the jacket checked off the list, I made one final stop at CVS.

The shopping trip itself wasn’t memorable.

The security system was.

If you’ve followed the news over the past few years, you’ve probably heard stories about retailers locking up everyday items because of organized theft. Seeing it in person, though, was something else entirely.

As soon as I walked in, an employee greeted me and asked what I needed.

When I told her, another employee—a very large gentleman—personally escorted me to the aisle.

He unlocked a plastic security case, handed me the item, locked it back up, and then walked away.

The whole process took maybe thirty seconds.

I couldn’t help but laugh.

Not because it was funny, exactly.

More because it felt surreal.

It was one of those moments where reality seems stranger than anything you could have made up.

With my errands finally complete, I headed back to the hotel.

I spent the evening mounting panniers, attaching camera poles, organizing batteries, securing the trailer, and making sure Lady Independence was finally ready for the miles ahead.

Everything was packed.

Everything was charged.

Everything was as ready as it was ever going to be.

Tomorrow, the planning would finally end.

Freedom Ride 250 would begin.