How to Plan a Road Trip

Two years ago, I set off on my solo 2-month road trip across the country. While that may sound fantastical and free-spirited (and it was), the truth is that prior to my departure date, I had spent a significant amount of time planning the trip. I was, after all, going to be living on the road for the next 8 weeks. I talked to friends to gather recommendations, I read through a book of National Parks, I reached out to acquaintances (some I knew, others I had never met) across the country to see if they would put me up for a night or two. In retrospect, it even seems a little odd, but at the time I was fearless and on a mission. I pitched a tent for the first time in my living room so I would have the gist of it for my first night of camping, ever. I watched YouTube videos on how to camp "simply", and figured out what gear I definitely needed, and then went and scoured Craigslist to obtain said items. I grabbed drinks with friends and said goodbye to my coworkers. Then I packed my car just barely to the brim, and headed out to stop #1, Ohio.

This post is meant to surface some of the artifacts from the trip that might help inspire someone else thinking about a road trip. I've posted my "best" photos in the past, but there are so many other behind-the-scenes details that went into getting to those places where I took the photos that I have never shared. The planning portion of the trip was arguably equally exciting (in its own way), as the trip itself. Without the planning, I question if the trip would have been so successful, and if I would have covered so much ground, seen so many interesting things, and met so many interesting people. Every single day on the road I was experiencing something new. I was seeing places I had never seen before. It was indeed an awesome and grand adventure.

The Map

This map was my project for the better half of a year before setting off on the road. I started with interesting cities (blue). I added National Parks (red), and "Other Fun" (green). This article from Thrillest became a main source of city planning--in retrospect, I didn't go to many of them, but it was a fun jumping off point. The route actually took a significant turn only a week before I left. My initial plan was to book it straight from DC to Colorado; but, over drinks with a knowledgeable friend, I was convinced to head north in order to hit the Badlands. To get to South Dakota, it seemed reasonable that I should just go all the way up to the Upper Peninsula, stopping to see family along the way (excellent choices in all regards).

The Itinerary

With my sideways zig-zag route taking form, I created a spreadsheet to map out quite literally every single day that I would be on the road. This was an incredibly useful exercise. I plotted out which days I actually had to be in places (i.e. I had concert tickets in Berkeley, and a music festival to be at in Oregon). From there, I figured out where else I could be, who I could stay with, or where I would camp. For the most part, I would spend 3-5 days on my own camping, then mix in a city or a stay with someone, and repeat. After the first month, I had to sit down in a Starbucks in LA to plan what the second month looked like. At that point, I had the hang of things, and it only took an hour or two!

etc. for two months

The Packing List

Reading through this list now, I think it definitely still holds up for any road trip. It's rooted in essentials...I was, after all, only driving a sedan, and space was not unlimited. The most useful items that you might not think about are as follows: headlamp, leather gloves for fire/firewood, ziplock bags, mallet (not listed) for hammering your tent spokes into hard ground. Also worth mentioning, I did not own a tent, sleeping pad, or sleeping bag. I found great quality items on Craigslist for cheap. I did invest in a well fitting day-pack and hiking boots from REI. Also, the 1.5L Smart Water bottles are excellent to slide into the side pockets of your pack!

The Budget

I attempted to estimate my weekly expenses, and approximate my monthly expense. While I did not keep a detailed log of my expenses while on the road, I would tend to say that these expense estimates were generous. Gas may have been more, especially in National Park areas where there is only 1 gas station in the middle of nowhere. Lodging was definitely less - the most expensive campsite I stayed at was $35/night at Big Sur. Everything else was $20 or less (usually less). Friend's couches are free; although, I tried to do the dishes or make breakfast when possible! Groceries seems about right. Dining out I would say was almost non-existent. I had 1 memorable meal, and ate out occasionally (maybe 1x/2 weeks), so I think this was less. As for Recreation, I can't think of much I spent additional money on. I'd encounter a state park or museum fee here and there, but otherwise my main source of recreation was hiking. The National Parks Pass is a one-time fee with access to everything for a year.

* * *

The planning piece of the road trip was both fun and invaluable to the success of my trip. I'm sure other people have "winged-it" and also had a great time; but for me, this is what helped me wrap my head around what I was actually about to set out and do.

Once I was out on the road, I had some flexibility to head in different directions, if needed--for example, I was in Colorado when fires were happening in Durango, and I had to shift my route. I think it's worth leaving enough room for some spontaneity, because I would get recommendations from people I met everywhere I went, and those were always some of the best ideas!

I hope this is helpful for anyone thinking about a road trip in the future!



For all the cool photos, check out

Here's a few extras that serve as evidence of some of my points above.

I stopped at the Maroon Bells in Colorado based on a recommendation from a friend of my cousin, who I had never met, but generously let me sleep on her couch in Denver!

I did not spend much money on dining out, but this Gin & Tonic from my "most memorable meal" was one for the books. I'm going to keep the establishment a secret ;)

I loved stumbling across farmers markets, especially on weeks where I was camping. Not only do you get a taste of the local scene, but you can get fresh, local, and usually cheaper produce!

If you get really lucky, your good friends will need you to house- and dog-sit for them the week you are stopping through town!