20 New Places in 20 Days (And Why Your City Might Be Cooler Than You Think)


4 min read


“I always wonder why birds choose to stay in the same place when they can fly anywhere on the earth, then I ask myself the same question.” -Harun Yahya


For my first 22 years on earth, I lived in the same city. And while I knew most of the cool parks, restaurants, hiking trails, parks, gyms, libraries, and coffee shops around the area, I still hadn’t explored every part of town. After 22 years, there were still parks I hadn’t explored, restaurants I hadn’t tried, and coffee shops I had never stepped foot in.

Recently I was thinking about how strange this was. I was capable of going anywhere I wanted to around the city, yet on a weekly basis I always went to the same predictable places: my home, the office, the gym, the library, and Chipotle.

So, when I moved into my new apartment a little over a month ago, I decided to challenge myself: I wanted to go to 20 new places in 20 days. I wanted to see what this new city had to offer. 

First, I brainstormed some places I would like to find:

  • Libraries
  • Coffee shops
  • Bookstores
  • Restaurants
  • Hiking paths
  • Parks / Nature reserves
  • Basketball courts
  • Frisbee golf courses

Next, I decided to use two techniques to find these places:

Technique 1: Google Maps (The modern, lame approach)

I would literally type in “parks”, “coffee shops”, and “libraries” into Google Maps to find places nearby.

Technique 2: Drive down random roads (The old-school, adventurous approach)

In the evenings after work, I would hop in my car and just start driving down roads that I had never driven down before.

Here’s Where I Went

In total, I went to 20 new places but it took 30 days to do so. Some nights I was just too busy, sometimes life got in the way, and in the middle of this challenge I went to FinCon for four days. 

Here’s a list of every place I went to along with a few notes I jotted down about each place.

1. Basketball court #1 “Found a basketball court today 5 min. from my apartment, pretty old and in a sketchy area, I probably won’t go back.”

2. Basketball court #2 “Found another random court today driving through an old neighborhood, looks super new, nobody was there, I’ll definitely come back often.”

3. Mexican restaurant “Tried out a Mexican restaurant 10 min. down the road today with *****. The Yelp reviews were really good, but the food was awful. Chipotle is higher quality and cheaper. Won’t be coming back.”

4. Nature reserve #1 “Explored a massive nature reserve 10 min. away that had a ton of hiking trails, lots of picnic areas, and a huge lake. Very cool area, will definitely come back.”

5. Library #1 “Went to a library 10 min. away, staff were super nice but there wasn’t much seating and the lighting wasn’t great, probably won’t come back.”

6. Frisbee golf course “Found a neat frisbee golf course near the nature reserve I explored a couple days ago. Played with **** and *****, pretty easy course, we lost one disc though and saw a snake, which made things interesting. Will probably come back.”

7. Basketball court #3 “Stumbled across another random basketball court today in a neighborhood. It was pretty old, the nets on the rims were falling apart, probably won’t come back.”

8. Public garden “Walked around in the public garden near my apartment, super nice area, lots of walking paths, seems like a popular place for people to walk their dogs, will definitely come back.”

9. Skyline “Went to the Skyline down the road with *****, got three cheese coneys, pretty solid. Also entered a drawing to win a cheesy Skyline Christmas sweater. Fingers crossed I win, that would be hilarious. Will definitely come back.”

10. Dairy Queen “Finally tried the Dairy Queen right down the road with the bros. When we went up to order, we noticed there was a huge spider on the window, started looking around more and saw there were literally hundreds of spiders crawling all over the walls of the place. Promptly sprinted to my car and opted to go through the drive-through instead. Will probably still come back despite the spider infestation. DQ is way too delicious.”

11. Movie theater “Saw the movie Free Solo at a tiny movie theater downtown. Super clean and nice staff. Will probably come back at some point.”

12. Nature reserve #2 “Found a new trail that I missed at the nature reserve I went to last week. This trail was awesome, super rugged, walked along a swampy area for a couple miles, didn’t see anyone the whole time. Now that I’m actually typing this out, I’m wondering if that trail was supposed to be closed…oh well, will definitely come back again.”

13. Pizza place “Tried out a tiny hole-in-the-wall pizza place with the bros tonight. Pretty mediocre pizza. Won’t be coming back.”

14. Library #2 “Drove by a random library today, stopped and turned around. Super nice, lots of windows inside, plenty of seating, and had a courtyard to look at while working. Will definitely come back.”

15. Coffee shop #1 “Tried out a new coffee shop 10 min. away. It had a very odd layout, kinda like a warehouse, then I find out that they actually supply the coffee beans for most Cincy coffee shops. I was the only person there from 6am – 9am. Neat place, but I probably won’t go back.”

16. Coffee shop #2 “Found a tiny coffee shop right down the road that I had never noticed before. Very tiny inside, but it had lots of character. Tons of plants on the walls, friendly staff, lots of windows. Only drawback is that they don’t open until 8am on the weekends. Will definitely come back.”

17. Cemetery “Drove down some random roads tonight and stumbled across a cemetery that overlooks the city. Sat and read a book for a while. Not sure if you’re supposed to read in cemeteries, but it was super peaceful. Probably won’t come back.”

18. Nature reserve #3 “Went to a small nature reserve today. Super tiny, but had some nice trails and wooded areas. Will probably come back.”

19. YMCA “Finally tried out the YMCA down the road. Incredibly tiny, not much equipment, felt cramped. Definitely won’t be back.”

20. Juicery “Went to a juicery in downtown today, got a delicious fruit-based drink, but it was super expensive. Cool atmosphere, lots of plants, good lighting, but probably won’t be back. Not exactly my setting.”

This chart shows the 20 places I went to based on the type of place:

What’s the Point?

One reason I wanted to do this challenge was just to find some cool spots around town that I wasn’t familiar with. The other reason was to add some variety to my life. I find that when I do the same things day in and day out (wake up, go to work, go to the gym, come home and chill, go to sleep), the days and weeks tend to blend together. This seems to make time pass quicker.

By going to new places, it breaks up the monotony of my daily schedule and adds some variety to my life. In a sense, it helps slow down time.

Try it Yourself

Try this challenge yourself. You don’t have to be strict about it. Go to 10 new places in 10 days. Or 10 new places in 20 days. Or 20 new places in 30 days. Just pick a number and get going. You might find that your city has more to offer than you thought. 


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9 Replies to “20 New Places in 20 Days (And Why Your City Might Be Cooler Than You Think)”

  1. In our area out west, we love driving around the town. We have found more places by just driving around. Coworkers and friends say why were you in that neighborhood, when you live over in that neighborhood. Because I want to explore the town. Funny thing about libraries, whenever we visit other states and cities, we check out the libraries. If you ask nicely and explain that you don’t live there, but would like use the computer for internet, they will let you. Granted nowadays the phones are probably faster.
    Too bad we don’t live nearby, I would invite you to bball on Saturdays over here. Granted we are a bit older and slower, but still hoop. 30-62 yo. Ha ha.

  2. I do this too from time to time (i.e., take a different route to work or drive around during lunch). There are so many places just locally that I learned about and can now appreciate. The adventure continues 🙂

    1. I like driving around during lunch occasionally too, it’s an easy way to explore some nearby places I’ve never been before. It’s cool to hear that you do the same 🙂

  3. That’s a super cool challenge Zach! Great job stepping out of your routine. Challenge accepted over here! If I can count yesterday I already have 1 new place in the bag despite it being in our neighborhood, where we’ve lived for 3+ years. Exploring a city in this adventurous fashion is on my list of how to approach retirement actually, but with less structure than you present above. I need to add more structure to it! One goal I have before we start retirement is to walk every street in Seattle. Someone did this in Manhattan while I was living there and I remember being so inspired. I’m going to start mapping out how I can do that as well in the next few years. It’s crazy what you can find when you get off your beaten path. Thank you for the inspiration as always!

    1. I love the idea of walking every street in a city. That would take some serious time but I imagine it would be a great way to find some neat places. Cheers to finding new places 🙂

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