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My Road Trip, My Way: Books, Outfits, and Adventure
- Theresa Wilson
- 2 days ago
- 6 min read
There’s a particular kind of calm that settles in right before a road trip. Not the quiet kind where nothing is happening—but the in-between kind, where everything is slowly coming together.
It usually starts with small piles forming across my space: clothes I’m debating between, snacks being sorted into containers, books stacked and reshuffled more times than I care to admit, and notebooks opening and closing as I refine what I want this trip to feel like—not just practically, but mentally too.
Because for me, road trips aren’t just about getting from one place to another. They’re something I want to experience and reflect on while it’s happening. That’s why I always bring my reading journals, along with an extra journal just for the trip itself. Not just to document it after the fact, but to actually slow it down in real time.
This is one of my favourite parts of travel—the preparation stage. Because long before the road starts moving, there’s this entire version of the trip that exists only in planning. And in a way, that’s where it really begins.
Meal prep: keeping the road simple
Food is one of those things that can quietly shape the entire rhythm of a road trip.
Over time, I’ve learned that a little intention here makes everything smoother. I don’t overcomplicate it, but I do like having a plan so I’m not making random decisions at gas stations or rushing to figure things out mid-drive.
I plan my meals separately in a dedicated journal, keeping everything simple, practical, and realistic for travel.
That usually includes:
easy breakfasts before leaving
snacks that are actually road-trip friendly (nothing messy or complicated)
something more filling for longer stretches or picnic-style stops
and a few treats, because road trips always feel better with them
It’s not about being strict or overly structured—it’s about removing small moments of stress later on.
When I’m on the road, I want food to already be decided so I can stay present in everything else happening.
Outfits: comfort, layers, and real-life practicality
Outfits for road trips are never about perfection for me. They’re about comfort first, practicality second, and feeling like myself in whatever version of the trip unfolds.
Instead of planning strict outfits for each day, I think in layers and combinations that can adapt to changing weather and different stops along the way.
That usually looks like:
comfortable basics for long driving days
layers like hoodies, sweaters, and light jackets for flexibility
shoes that work for both sitting in the car and walking around
and a couple of outfits that feel a bit more put-together for spontaneous plans
I do also like having a few planned outfits in advance, simply because I enjoy having that sense of structure before a trip. But even those are never rigid—they’re all built from pieces that can be swapped, switched, and mixed together so everything still works interchangeably. It gives me the comfort of planning without locking me into specific “day-by-day” outfits.
I’ve learned not to overpack in this area anymore. I used to bring way too many “options,” but I almost always end up wearing the same few pieces that actually feel right on the road.
Now I focus on versatility instead of variety—and it makes everything feel easier, not just when packing, but while travelling too.
Books: choosing what comes with me
Books are one of the most intentional parts of my packing process.
I don’t bring a huge stack anymore because I’ve learned I won’t realistically get through everything. Instead, I focus on a small, thoughtful selection that actually matches how I read while travelling.
For this trip, I’m bringing five physical books, which feels like my current sweet spot—enough variety to choose from, but not so many that it becomes overwhelming.
Alongside those, I always bring my Kindle as a backup, just in case I finish something faster than expected or want extra flexibility without carrying more physical weight.
And as always, I’m also bringing my reading journals, along with an extra journal just for this trip, because I don’t just want to experience the road trip—I want to reflect on it as it’s happening. There’s something really important to me about being able to slow moments down on paper, to capture thoughts while they’re still fresh instead of letting everything blur together later.
My reading choices usually follow mood more than anything else:
something light and easy to dip in and out of
a couple of books I’m genuinely excited to sink into during downtime
and a small “just in case” buffer that stays in my bag without pressure
There’s something really grounding about keeping it minimal and intentional. Each book feels like it has a place in the trip instead of just being part of a pile I feel like I should get through.
It makes reading feel more present—and more connected to the actual experience of being away.
The packing process: where everything comes together
This is the point where everything shifts from planning into action.
I usually start by laying everything out first instead of immediately packing it into bags. Clothes on one side, books nearby, travel essentials spread out, and my journals open somewhere in the middle so I can refer back to what I planned and what I actually want the trip to feel like.
Then I slowly start building everything into something that makes sense for the road.
This is also where my Chapter & Compass Master Road Trip Planner becomes a key part of my process—but not just for packing. It’s more of a full road trip system that helps me see the entire trip clearly before it begins.
It includes things like:
campground and accommodation reservations
weather tracking and general trip conditions
route planning and stop breakdowns
travel logistics and timing between destinations
car packing systems (bins, storage, and organization layout)
and all my packing lists in one place
So instead of just thinking about what I need to bring, it helps me think through how the entire trip flows from start to finish.
It keeps everything grounded and organized without me having to hold it all in my head at once.
From there, I move into actual packing:
comparing what I’ve laid out with what I realistically need
removing anything that feels unnecessary or redundant
rethinking what I’ll actually use versus what just looks good in theory
and adjusting things as I go instead of locking decisions in too early
There’s always a bit of reshuffling. I’ll pack, step back, change my mind, and repack at least once. Sometimes more. But it doesn’t feel stressful—it feels like part of getting everything to sit right before leaving.
And I think that’s really what this stage is about. Not just packing, but transitioning into the trip itself. Turning everything from plans into something real.
The small rituals before leaving
Right before a road trip, I always fall into the same quiet habits without really thinking about them.
One last check of everything.
A drink in a travel mug I probably won’t finish in time.
Standing in the doorway for a few seconds like I’ve forgotten something important.
And then finally sitting in the car and feeling that shift from preparation to movement.
That moment—the one where it clicks that we’re actually leaving—never gets old.
And somewhere in that transition, I already know I’ll be opening my journal at some point soon, starting to capture the feeling of it all before it slips into memory.
Leaving room for the unexpected
Even with all the planning, I try not to overfill the structure of the trip.
Some of the best parts of road trips come from things I didn’t plan at all:
unexpected bookstore stops
scenic viewpoints we didn’t know were there
small cafés in towns we only passed through
or spontaneous decisions to take a different route
I like having a system in place, but I don’t want it to close anything off.
The planning is there to support the trip—not define it.
And the journaling side of things helps me hold onto those unexpected moments while they’re happening, instead of just remembering them later in fragments.
why I always come back to this process
For me, road trip prep isn’t about making everything perfect.
It’s about making everything easier—and more meaningful.
It’s about slowly building a version of the trip that feels thoughtful and grounded so that when I finally get on the road, I can actually be in it. Not organizing it. Not stressing about it. Just experiencing it and reflecting on it as it unfolds.
Meals are planned just enough to remove stress. Outfits are chosen for comfort and practicality. Books are selected for mood and moments. Journals come along so I can actually hold onto the experience while it’s happening. And everything comes together in a way that feels intentional, but never overwhelming.
And that means when the road starts, I can let go of the planning and step fully into the experience.
And that’s really the goal every time—a little planning, so there’s a lot more room for adventure.
If you’re planning your own road trip, I’d love to know what your prep looks like—are you someone who plans every detail ahead of time, or do you keep things a little more loose and spontaneous?
And if you enjoy this kind of behind-the-scenes planning, you’ll probably also love my Chapter & Compass Master Road Trip Planner—it’s what I use to keep everything from packing lists to routes and reservations organized in one place, without overcomplicating the process.
May your heart stay warm, your pages stay full, and I’ll meet you in the next chapter. ✨