Follow along with @maddiekayphoto and I on our picture filled 4 day weekend traveling down the Oregon coast. Filled with picturesque small towns, wineries, and everything in between.

Day 1: Portland -> Canon Beach

After arriving in Portland late Friday afternoon, we headed to Thrifty to pick up our rental car. Because we would be driving a good portion of the trip, our original plan was to get a safe, chill, mom car. Well that plan went right out the window when the sweet Thrifty man offered us a deal on a one that would be way more fun. We ended up with a white 2020 Camaro, nicknamed Kacey…although we looked WAY cooler, it was not our smartest decision.

Hot Tip - I do not suggest getting a small sports car for a trip like this. We had multiple incidents that had us severely regretting our decision.

On the road, feeling FLY in Kacey, we started the two hour drive to Canon Beach. For the most part, the route was filled with treacherous curves and poorly lit backroads…be safe!

That night we stayed at the Inn at Haystack Rock. It couldn’t have been more convenient and easy to locate. (Not too mention it was really cute).

Day 2: Canon Beach -> Brookings

Haystack Rock was only a quick 20 minute walk from our Inn so we left our car and headed out pretty early. We made a beeline to Sleepy Monk Coffee for some much needed caffeine. I had heard INCREDIBLE things about this coffee shop and it did not disappoint.

Haystack Rock was breathtakingly beautiful, even with a bit of a crowd. This is definitely a must stop.

Tillamook.

On our way to Tillamook Creamery we made a pit stop at Pronto Pup for some corny dogs. They claim, the first corndog was invented in Rockaway Beach Oregon. Being from Texas, where Fletcher’s Corndogs alleges they were the first, I am partial.. Either way the Pronto Pup corndogs hit the spot.

I think we were a bit overly excited about visiting Tillamook Creamery, but the cows were calling our names. We spent way too much time learning about the cheese-making process and savoring mouth watering ice cream.

Thor’s Well.

With our bellies full of corny dogs & ice cream (health is our first priority), our next stop is a photographer’s favorite. We arrived to Thor’s Well close to sunset. Though it was low tide, it was still an absolutely incredible view.

Hot Tip - Check the tides before going. The best time to experience Thor’s Well is during high tide.

Brookings.

…and 5 hours later we reached our destination. It was a long drive but the scenery and views of the Oregon coast were totally worth it. If we were to do it again, we would definitely be better about keeping to a schedule. I would highly recommend taking a break somewhere along the way to make the drive not as monotonous.

Day 3: Brookings -> Rogue Valley

After a long, exhausting drive the night before and the coziest cottage surrounding us, we ended up sleeping in a little before starting our next mini road trip.

If you are ever looking for an Airbnb in Brookings, Debra was one of the nicest, most accommodating people I have ever met. Not only that, we truly felt like we were in a little cottage by the sea. I only wish we had had more time to spend relaxing and taking in the views. On our way out of town Debra suggested we explore Chetco Point, which you can see from their house.

Chetco Point.

With coffee in tow, and Debra’s directions fresh on our brains, we were en route to Chetco Point. The pictures below speak for themselves. I felt like I was back in Ireland exploring the Cliffs of Moher. Debra was 100% right, it was breathtaking and I am so glad we took this little detour.

Warning: do not complete this hike if you are afraid of heights!

Rogue Valley Wineries.

On the road again! 4 hours later, through California, on the last leg of our trip we made it to Rogue Valley. Surrounded by rows upon rows of grapes, the entire area was absolutely stunning. The Hummingbird Estate is a winery with quaint little suites built above the tasting room. We learned that at one point it did in fact belong to a family. We stayed in the Syrah Suite, overlooking the terrace and the beautiful mountains around us. I would highly recommend staying here! Our original plan was to check-in and wine hop. We ended up just staying at Hummingbird all night and man am I glad we did.

After frolicking around the estate, with our wine in tow, (you get a free can if staying the night) we headed to the tasting room for more wine and food. We snuggled up in blankets outside by the fire, ordered the most delicious meatballs and bread, and sipped a white wine flight (my favorites were the Estate & the Late Harvest). Sadly, the Estate only offers appetizers, since the tasting room closes at 7, but the staff was incredibly nice and we were able to DoorDash a pizza for dinner. Once the sun went down, it was chillier than expected and we quickly retreated indoors to eat dinner and relax. It was much needed after a weekend packed full of adventures.

Day 4: Travel Day

Travel time back to Portland was about 4 hours from the wineries. And there ya have it folks! We can’t wait to share all of our upcoming adventures with you all!