Road Trip Through Oregon

We set out on our first road trip together in the USA.


2 minute read

Last Month, Jordan and I were able to set out on our first road trip from Oregon down to California. We didn’t realize how fun the stop along the way would be.

Driving down from Oregon to California is a 13+ hour drive. Basically the distance from Johannesburg to Cape Town in South Africa. That’s when I really realised how big America is.

The first stop we made was in Jacksonville, Oregon. I didn’t know this place existed before our trip, but fortunately my sister-in-law gave us the suggestion to stop by on our way down. And we’re so glad she did! It’s the cutest little town I’ve ever seen, there are quaint restaurants and shops lining the main street, with cute doors and walls screaming, “Such an Insta-moment!”

Jordan at Levi's Wall Diane by a cute blue door in Jacksonville

We only fully began to appreciate how lovely Jacksonville was in the day time (we first arrived late at night). As you enter you see plots of land with old houses and it does have a bit of a horror movie vibe at night upon entry, before reaching the main street. I really laughed out loud when we took the exit towards Jacksonville and Jordan says: “I hope it’s okay to be black out here”.

Turns out it was okay; and we later found out just how friendly the people are in Jacksonville when Jordan stopped the car on the side of the road to get something from the boot (trunk). Several people stopped to check if we were okay, assuming our car had broken down.

We rented a place to stay using Airbnb. It was the best Airbnb experience of my life thus far! Our host was so gracious and accommodating. With 5 bottles of wine to choose from, ciders and snacks on arrival, we felt right at home. One of the cutest touches in our place was a pile of stones that the host requested guests to leave a message on, to be used to decorate her fire pit. So sweet!

Jacksonville AirBnb Jacksonville AirBnb

She recommended we come back in the summer months to enjoy the variety of concerts held at theĀ Britt Pavilion. After looking up a few of the artists (including Ziggy and Stephen Marley), we might find ourselves driving down there again in the near future! For more information about the Britt Fest lineup, check outĀ

So if you’re looking for a cute road trip stop in Southern Oregon, do yourself a favour and visit the cute, friendly town of Jacksonville, Oregon.

Jacksonville Street Corner Jacksonville's 'California Street'

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