A Girls Road Trip Through Oregon

Girls Trip through Oregon in Cannon Beach

Miranda and I take an annual summer trip to explore somewhere new and do something different. This year, we did a girl’s trip through Oregon. We flew out for a week, rented a car, and saw all we could in our time here. Check out the gallery at the end of this post!

Here is our version of a girls trip in Oregon:

Day one we landed in Portland, picked up our rental car and headed to University Place Hotel & Conference Center. It was the perfect quick stop that was cozy, clean, and conveniently located. After checking in and freshening up from the long flights, we wandered around Portland and grabbed dinner at Tope. It is a charming, rooftop restaurant and bar located inside The Hoxton Hotel with margaritas and tacos!

While Portland was not one of our longer stays on this trip, we made sure to visit Powell’s Bookstore to stock up for the trip and Donuts from breakfast from Voodoo Doughnut. As tourists, it would be wrong not to stop at both!

Smith Rock State Park & Bend

The next morning, we officially headed out on our Oregon road trip and drove 3 hours to Smith Rock State Park near Redmond.

We hiked The Misery Trail which feels appropriately named… The trail is about 4 miles around the park. It starts with some pretty intense uphill switchbacks that will bring you to the top of the ridge for some amazing views. It is all downhill after that with more shade, wildlife, and beautiful views. You’ll see rock climbers enjoying the morning and plenty of other hikers taking in the natural scenery. 

Definitely start this hike earlier in the day. You will start out on the most intense part of the hike directly in the sun, assuming you go right like we did. Bring plenty of water and snacks for refueling. It wouldn’t be the ultimate Girls Trip through Oregon if you don’t want to pass out a little while hiking.

We drove 40 minutes to Bend and stayed in the Campfire Hotel. We got dinner at Boneyard Pub, which has some fantastic food and strong drinks. This was defiantly one of our favorite food stops on the trip. We sat outside, enjoyed nachos and several drinks while planning for the coming days.

We stayed two nights in Bend to explore the scenery and local color. Shopping in the Old Mill District and dinner by the water from Greg’s Grill. We grab breakfast at Cafe Des Chutes and walking around the shops at 50 SE Scott St. 

We also spent a lot of time enjoying the Campfire Hotel and all they have to offer!

Tamolitch Falls, Salem & Silver Falls State Park

After leaving Bend, we drove out to Tamolitch Falls in Lane County. Here, you can hike 2.5 miles to the Blue Pool. This was easily my favorite hike of the trip. The hike is through beautiful forest and puts you out at the Blue Pool which is unlike anything I have seen. The pool is made by a natural underground spring and seems unreal with how blue it is. The trail itself is a pretty easy, flat hike that puts you above the pool. To get down where you can get in is a slightly treacherous climb down so be prepared. You can jump in the pool which is an average of 37 degrees. We brought sandwiches and enjoyed lunch before climbing back up and hiking the 2.5 miles back. 

Girls Trip through Oregon

We drove to Salem for the night before heading out again. While we would have loved to explore the city more, most shops were closed by the time we arrived and left early the next morning to drive to Silver Falls State Park. We hiked the Trail of Ten Falls but cut across the Winter Trail to cut it a little shorter. While some things say this trail is 7 miles, others say the trail is closer to 9. By cutting across, we still saw 7 of the falls and hiked 6 miles. Most of the trail is pretty flat with certain trails that are more accessible to those who cannot hike the entire trail. 

Tillamook Bay & Coastal Highway

We drove 2 hours to Tillamook Bay where we stayed at The Hotel Garibaldi and had dinner at Sand dollar restaurant and lounge. A perfect stop to enjoy drinks while watching the sunset.

We drove up the Coastal highway and stopped at a few antique stores and fun shops on our way to Cannon Beach. We grabbed lunch at the Pirates Cove Restaurant. They had great seafood dishes and the best view of the water below. Their desserts were also giant and looked amazing! This restaurant is a must on your drive!

Cannon Beach & Ecola State Park

We stayed 2 nights in Cannon Beach at The Lighthouse Inn. Though the room didn’t have AC (most don’t in the area), the room was lovely and the hotel offers fresh baked cookies, had a rootbeer float party, and gave us post cards to mail back home. It was a fabulous little place!

During the two days we spent at Cannon Beach, we explored the town, read on the beach, saw the tidepools, and enjoyed some downtime. We made our way out to Ecola State Park and hiked the Clatsop Loop which was about 3 miles and while hilly, was a relaxing, shaded hike with great views of the beach and lighthouse.

Girls Trip through Oregon in Cannon Beach

We tried a few different restaurants like Bill’s Tavern & Brewhouse and Pelican Brewing for dinner, Insomnia Coffee Co and Sleepy Monk Coffee Roasters for breakfast and grabbed from late night drinks from Other Brother’s Bar.

All in all, this timeline worked out perfectly for us. We felt like we had enough time at the places we wanted to see, had plenty to do without being too overwhelmed and a good amount of time between hiking to recover.

You can download our full Girls Trip through Oregon itinerary now!

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