how to: plan a weekend road trip

“To my mind, the greatest reward and luxury of travel is to be able to experience everyday things as if for the first time, to be in a position in which almost nothing is so familiar it is taken for granted.” – Bill Bryson

As much as I would like to spend weeks traveling the globe, my kind of travel is generally of the long weekend road trip variety. Living in Colorado makes finding beautiful places easy but - trust me - there are hidden gems near anyone. 

People ask me a lot of questions about road-trips: how I decide where to go and how I find interesting places when there. While most of my advice is common sense and you probably do most of it already, hopefully I can give you some kind of new tool to make your planning less stressful or some inspiration to start planning (Memorial Day is around the corner!). So here is the first of a series of "how to" posts covering some basics of short road-trip planning. 

car window

First: Where to go??

The first thing I do when I have a long weekend or am itching to get away is to look at a map. I start in Denver and search a radius of 4-6 hours in any direction for place I haven't been.

denver map


A good strategy is to find the green on a map and zoom into it! This is what I got a couple weeks ago zooming in to the Rapid City area. So many places I never would have thought about!

rapid city map

Second: Where will I stay?

After finding the area I want to go to I generally will start an airbnb search. I set the map to the same places, filter it to my price range and entire home with the dates I want to travel and see what comes up. If you haven't used airbnb before, my advice is to go for places with lots of reviews 4 1/2 stars and up. I've had only really great experiences this way. 

airbnb rapid city

If there isn't anything I like I move the airbnb map around with the cursor to see if anything else pops up. Just make sure to keep it within the distance from home that you want to travel.

This also helps with finding unique places. The best places I've stayed (tiny houses, domes, etc.) are "off-the-grid" in some form so it's worthwhile to look in the outer areas. They are also generally cheaper!

This trip didn't have a deal good enough for me so I went on to Hotwire

Love a straightforward hotel. 

Love a straightforward hotel. 

As you can see, hotels tend to be much cheaper in this area. Personally, I also knew that the objective of this trip was to spend as much time as possible visiting things outside of the hotel so having a swank or interesting place to sleep wasn't as important to me. 

I don't make the actual reservations just yet though! I just need to know where the best accommodations are to direct the rest of my search. 

Third: What will I do while I'm there?

Sometimes I visit places for a specific reason, sometimes just because I haven't been there, but generally it's a combination of both. I had never been to South Dakota, but I knew I wanted to visit Mount Rushmore. After that I was open to anything. 

Again, looking at a map is a great way to start. That's how I found that Badlands National Park was within a day trip of Rapid City. I also put Custer State Park on my list from the map. 

Reading other blogs is a great way to find well known and less known attractions. I usually start with a Pinterest search and go down the rabbit hole for a bit, pinning posts and taking notes of places that seem interesting or that keep coming up in posts. 

black hills pinterest

I also always look at the "things to do" section of TripAdvisor. It's based on reviews from real people so the content and ratings are genuine.

trip advisor

 I look at the general vicinity and also the specific city I'm staying in. The Rapid City TripAdvisor page is the reason I got to see this dinosaur: 

dinosaur park

Another great way to find interesting local attractions is instagram! Hashtags and location tags are seriously how I've found some of the greatest places I've ever been. 

I also do this with the locations I visit to make sure I don't miss out on a cool spot. It's also a great way to get inspired and excited for a trip. 

Instagram led me to Art Alley in Rapid City, an awesome alley downtown full of street art. (look out for a dedicated post - so great to find in South Dakota)

Fourth: List making!

After I have some ideas/notes/maps I write out actual distances between the places I want to go to find the best route. This (of course) starts by looking at a map and getting a general idea for what's going to be the smartest route. Then I look up distances between the points and come up with an itinerary. This helps me feel more organized and makes the best use of my time. Not a minute is wasted! 

This is what I ended up with for the Black Hills trip: 


I didn't end up making it to Wind Cave National Park or Chapel in the Hills but knowing the possibilities made the actual trip much less stressful. 

Fifth: Book it!

Book the trip! Take the day off, confirm the hotel/airbnb/tickets etc. Be confident that you have planned an amazing trip and focus on the fun stuff!