The Ultimate Oregon Road Trip

Oregon has been on my bucket list ever since bucket lists became a thing. This past year, I made a promise to myself to start shortening my list of must-do's. Nine days seemed like a stretch time-wise—after all, there's that thing called work that always seems to get in the way. But as soon as I got the thumbs up from my boyfriend, the planning began.

Oregon is vast and diverse, offering everything from snow-capped mountains to stunning rocky shores, rugged backcountry hikes, quaint towns, and bustling city centers. The challenge was figuring out how to see as much as possible without feeling rushed. We could have easily planned a multi-week adventure and still not scratched the surface, but with life calling, a 9-day trek would have to do the trick. And just like that, the planning was underway.

With the help of more Pinterest sites than I'd like to admit, countless hours of surfing the web, and picking the brains of a few well-traveled friends, this epic trip was born.

Day 1: Portland - Kimpton Riverplace Hotel - Exploring the waterfront and Downtown Portland

Day 2: Exploring Portland’s Serenity and Flavors

Our day began with the peaceful ambiance of the Portland Japanese Garden, followed by a visit to the stunning International Rose Test Garden. After soaking in these natural beauties, we headed downtown to explore the heart of Portland.

We spent the afternoon hopping between some of the city's coolest breweries, sampling ice-cold brews and indulging in delicious snacks. Deschutes Brewery stood out as our favorite, offering a perfect mix of great beer and a lively atmosphere.

As the evening approached, we made our way to Ava Gene's for an unforgettable dining experience. Known as one of Bon Appétit's "Best New Restaurants in America" back in 2012, Ava Gene's continues to impress with its Roman-inspired menu, showcasing the finest seasonal ingredients from the Pacific Northwest. We indulged in a six-course chef's dinner, where each dish was paired with wine, making for a truly memorable culinary journey.

Day 3: The Road to Mount Hood

Our third day began early with a quick Starbucks run before we set off on an unforgettable journey along the Historic Columbia River Highway Scenic Byway. This 70-mile route runs along the Columbia River, separating Oregon from Washington, and is celebrated as America’s first scenic highway. Known for its breathtaking waterfalls, panoramic views, and rich history, the byway offers a truly iconic experience.

While the drive from Portland to Hood River takes about an hour on I-84, we opted for the more scenic route. The Historic Columbia River Highway gave us the chance to stop at some of the 80 waterfalls just off the road, including Latourell Falls, Multnomah Falls, Bridal Veil Falls, Wahkeena Falls, and Horsetail Falls. We were eager to beat the crowds, so hitting the road early was key to fully enjoying these natural wonders. The serenity and beauty of the waterfalls set the perfect tone for our journey to Mount Hood.

Stop 1: Vista House

The Vista House is a stunning stop along the Historic Columbia River Highway, perched high above the Columbia River Gorge. Built in 1918, this elegant, octagonal building with its copper dome offers incredible panoramic views of the river, surrounding cliffs, and forests.

We stopped here to take in the sweeping scenery, and the views didn’t disappoint. Inside, the Vista House feels like a blend of history and beauty, with its marble floors and stained-glass windows. It’s a peaceful spot to pause and soak in the natural beauty and history of Oregon before continuing on our journey.

Stop 2: Latourell Falls

After leaving the Vista House, our next stop was Latourell Falls, one of the many stunning waterfalls along the Historic Columbia River Highway. This 224-foot waterfall drops straight down a basalt cliff, with striking yellow-green lichen adding a vibrant splash of color to the scene.

The best part? We arrived so early that we had this magical place all to ourselves. The solitude made the experience even more special as we took a short hike to the falls, feeling the mist on our faces and soaking in the peaceful atmosphere. It was the perfect moment to connect with nature before continuing our journey.

Stop 3: Wahkeena Falls and Multnomah Falls

Our third stop was Wahkeena Falls, known for its distinctive multi-tiered cascade. The waterfall flows down a series of rocky steps, creating a striking display of rushing water.

We followed an easy trail called the Lark Mountain Trail that meandered along the side of a mountain. Before we knew it, the trail led us right to the base of Multnomah Falls. The journey was a pleasant way to transition between the falls and added a nice surprise to our day of waterfall hopping.

Multnomah Falls is one of the most iconic and visited waterfalls in the Columbia River Gorge, standing at 620 feet tall. It features a dramatic two-tiered drop, with the upper fall plunging 542 feet and the lower fall cascading 69 feet. The falls are renowned for their impressive height and the picturesque bridge, Benson Bridge, which spans the lower section and offers a great vantage point for photos. We attempted to hike to the top but didn’t quite make it—laughing at our ambitious plan along the way. Despite that, the view from the base was impressive and a great addition to our waterfall tour.

Starving after our adventure, we decided to have lunch at The Restaurant inside the historic Lodge at Multnomah Falls. The pancake stack was to die for, and who doesn’t love a mimosa in the morning? It was the perfect way to refuel and relax before continuing our journey.

Regarding entrance fees: As of my last update, access to the Multnomah Falls area and viewing the falls themselves is free. However, during peak times, especially in the summer, parking in the nearby lot may require a fee or a parking pass. It's a good idea to check for any current parking fees or requirements before you go, as they can change.

Stop 4: Bridge Of The Gods

The drive from Multnomah Falls to the Bridge of the Gods typically takes about 30 to 40 minutes, depending on traffic and road conditions. The route involves traveling along Interstate 84, then taking Highway 14 across the river to the bridge.

The Bridge of the Gods is a notable landmark spanning the Columbia River, connecting Cascade Locks, Oregon, with Stevenson, Washington. It’s a toll bridge, and it provides a key crossing point for travelers heading into the Columbia River Gorge area.

The bridge itself is an impressive structure, both historically and architecturally. Built in 1926, it was named after a Native American legend and plays a significant role in the region’s transportation network. It’s a great spot to stop for a photo op and enjoy the views of the Columbia River Gorge from a different perspective. Of course, we had to cross!

After our visit to the Bridge of the Gods, we continued on our journey to our final destination: Cooper Spur Mountain Resort. The drive took us through some beautiful scenery, covering about 75 to 85 miles and typically taking 1.5 to 2 hours.

We headed east on Highway 14, then took Interstate 84 and Highway 35, enjoying the picturesque views of the Columbia River Gorge and the Mount Hood area along the way. The anticipation of arriving at our resort made the drive even more enjoyable.

Last Stop: Cooper Spur Mountain Resort

Nestled in the beautiful Mt. Hood National Forest, Cooper Spur Mountain Resort is the perfect escape into nature. Surrounded by pine trees, meadows, and clear waters, it’s a great place to relax and leave stress behind.

We stayed in a cozy log cabin with a full kitchen. That evening we enjoyed some tasty farm-to-table burgers at the Crooked Tree Tavern & Grill. The rustic vibe and delicious meals made our stay even better and wrapped up our trip perfectly.

Day 4: Chilling, Exploring, and Grilling

Our fourth day was all about relaxing and enjoying everything Cooper Spur Mountain Resort had to offer. We started with some laid-back time, taking in the peaceful surroundings.

We took a drive to Mount Hood Ski Resort and enjoyed the gondola ride up to the top, where the views were incredible. Afterward, we headed to Government Camp for lunch at Mt. Hood Brewing Company. The BLT wrap was hands-down the best I’ve ever had, and the beer was pretty great too!

We spent the rest of the afternoon exploring the resort, playing ping pong, and grilling up a tasty barbecue. It was the perfect mix of relaxation and fun, making the most of our time in the beautiful Mt. Hood area.

The Magic Mile Sky Ride at Timberline Lodge on Mount Hood's south face costs $18 per person for the gondola, and children 6 and under are free. The gondola is open daily from 10 AM–4 PM during the summer, and riders can see the summit of Hood, Palmer Glacier, and nearby Mt. Jefferson.

Day 4: Continued -LOL

After a relaxing day at the resort, we decided to squeeze in an evening hike. I know it sounds a bit crazy, but the fresh air and the idea of not missing out on any outdoor time was too tempting, especially with sunset not until 8:30 pm. I’d read about this magical place called Trillium Lake, and with a bit of convincing, Don was in too.

Trillium Lake is a beautiful spot in Mt. Hood National Forest, with calm waters reflecting the majestic Mount Hood. The hike around the lake is about 4 miles, but if you’re heading up to higher viewpoints, it can be more challenging with some steep sections.

When we arrived, the sun was already dipping, so we took a few quick pictures of the lake and the sunset in the distance. Realizing we’d run out of daylight soon, we hurried back down the mountain. We finally saw the exit just as the sun set, dirty, sweaty, and thirsty but with one of the greatest memories of our entire Oregon adventure. Just know what you’re getting into if you decide to tackle this hike!

Day 5: Sunrise at Mirror Lake

The next morning, we set out early for Mirror Lake. Although we didn’t quite catch the sunrise, the view of Mount Hood reflecting on the still waters of the lake was nothing short of breathtaking. With very few people around, the serenity of the scene made it a true highlight of our vacation.

The calm water perfectly mirrored the towering peak of Mount Hood, creating a stunningly beautiful scene that photos just can’t capture. It was a peaceful and memorable way to start our day, adding another magical moment to our Oregon adventure.

Lunch at Timberline Lodge

Timberline Lodge is an iconic mountain lodge located on the south slope of Mount Hood, offering stunning views and a classic alpine atmosphere. Built in the 1930s as a Works Progress Administration project, the lodge is known for its rustic charm, historic architecture, and beautiful surroundings.

We had lunch outside at one of the bars and it was a highlight of our trip. The chili was amazing, and we savored the best Bloody Marys we’ve ever had.

The views were unbeatable of Mount Hood. Off in the distance, we could see the part of the mountain still open for skiing. It was a fantastic spot to enjoy a great meal and take in the breathtaking scenery.

Evening Wind-Down

After some more exploring around downtown Government Camp, we headed back to our cabin to shower and refresh. We took a stroll around the resort and then settled in for a relaxing evening. We found ourselves enjoying a bottle of delicious Sauvignon Blanc and a charcuterie board loaded with meats and specialty cheeses from the tavern. It was the perfect way to wind down before calling it a night!

Day 6: Heading to McMinnville

The next morning, we packed up the car and set off for our next destination: the charming town of McMinnville. It was about a 2 to 2.5-hour drive from Cooper Spur, giving us plenty of time to enjoy the scenic route. Along the way, we passed through a few small towns, stopping to enjoy coffee at a local roaster. We also made a detour to Newberg, Oregon, to visit the Wayward Winds Lavender Farm. The drive was scenic and relaxing, setting the perfect tone for the next leg of our adventure.

Our Visit to Wayward Winds Lavender Farm

At the end of a long, winding road, we arrived at Wayward Winds Lavender Farm, and we were blown away by the sight. The beautiful rolling purple bushes swayed gently in the wind, creating a sea of lavender as far as the eye could see. This place is home to one of the largest lavender fields in Oregon, and the abundance of fragrant blooms made it a sensory experience like no other.

We explored everything lavender you can imagine—and even some things we hadn’t thought of. From award-winning essential oils and products to plants and refreshments, this farm has it all. There’s even a lavender maze, a bunch of chickens and a U-pick option for those wanting to bring some of the magic home. The vintage marketplace and rustic charm added to the experience, making it a truly unforgettable stop. Best of all, admission was free!

The Wayward Winds Lavender Farm

17005 NE Courtney Rd ,

Newberg, OR 97132

Open July 1 – August 14th* from 10-5 daily

*subject to lavender blooms lasting this late in the season

Next Stop: Wolves & People Brewery

On the hunt for lunch, we found ourselves at Wolves & People Brewery and Farmhouse. Set on a historic farm from 1853, this place blends old-world charm with modern brewing. The family has been working this land for generations, growing everything from hops to heirloom vegetables.

Their passion for beer is evident in every small-batch brew, crafted with pure well water and wild yeasts from their farm. The rustic barn setting made it the perfect spot to enjoy some unique, locally-inspired beers and take in the rich history of the place. We enjoyed some popcorn, I had a yummy sour called Sour Jawn and Don went with his favorite an IPA called Elemental Nature.

Next up - Lunch at Two Dogs Brewery, Checking into our tiny house at the Boutique Retreat in Downtown McMinnville, and burgers and beer and the Grain Station. (which was just ok)

The Boutique Retreat is an upscale Tiny House Hotel offering unique and distinct accommodations in historic downtown McMinnville, Oregon, the Heart of the Willamette Wine Country. With a 6-minute walk downtown. We LOVED IT! Each unit has a different theme, ours was a train car! You should check them out at https://www.theboutiqueretreat.com/

Day 5: Afternoon Wine Tasting at Eyrie Vineyards

That afternoon, we made our way to Eyrie Vineyards Tasting Room, just across the street. Though their estate vines grow in the nearby Dundee Hills, the historic winery is nestled in the charming town of McMinnville. Eyrie Vineyards has been making wine here for six decades, ever since they produced the Willamette Valley's first vintage of Pinot Noir back in 1970.

Their tasting room offers a rotating selection of wines from their organically-certified estate vineyards, featuring both innovative new varieties like Chasselas and Trousseau and classics like Pinot Noir and Chardonnay. We even got to sample some elite single-vineyard bottlings and a library wine or two from deep in their cellar.

The $40 tasting fee was refundable with a $120 purchase per person, which we had no problem covering. Let the wine collecting begin! (Side note: We’d smartly ordered a 7-bottle wine suitcase from Amazon for $150, which was delivered to our cabin at Cooper Spur—perfect for our growing collection)

Here's the link to the wine suitcase https://a.co/d/1DvROnH

Our host was amazing and incredibly knowledgeable, making the experience even better. Interestingly enough, Don and I had previously enjoyed their Pinot Noir on a recommendation from George Miliotis, a master sommelier from Wine Bar George in Downtown Disney, Orlando Florida who is also a family friend. It’s so yummy if you are a Pinot drinker, we highly recommend it.

And here’s a fun fact: I own a small wine bar called Spill in Winter Springs, Florida. This was my first official wine tasting outside of Spill. If you’re ever in the area, come visit me sometime!

Dinner at Jory Restaurant

After some relaxing, Don and I headed back to Newberg for our dinner reservations at Jory Restaurant, a farm-to-table gem in Oregon wine country. The experience was exceptional and gets a solid 10 out of 10 from us.

We dined on a beautiful balcony overlooking the grounds and pool as the sun set, creating a perfect atmosphere. The wine selection was impressive, and the steak was one of the best I’ve ever had. Although it wasn’t the cheapest meal, it was worth every penny.

Day 6: Wine Country

Stop 1: Soter Farms

Our first wine tasting of the day was scheduled for 11 a.m. at Soter Farms, so we knew we needed a good breakfast to start the day right. We walked downtown to a charming sidewalk cafe called Crescent Cafe. The food was delicious, but the bees were out in full force, so we tried to eat quickly and enjoy our meal before heading to our tasting.

Soter Farms was my favorite stop of the day. From the moment we walked up the gravel path from the car, we were treated like royalty. A lovely young woman greeted us with a delicious rosé and escorted us to our table. We had signed up for the exclusive MSR Provisions Tasting, which turned out to be an incredible experience. (Reservations are required, tickets are $150pp)

The Provisions Tasting is a guided culinary journey designed to showcase the bounty of Mineral Springs Ranch, their Biodynamic farm and vineyard in Oregon wine country. Seasonal cooking is a way of life here, with pairings changing weekly to match the farm’s seasons. Their goal is to source 100% of the ingredients from their property, and when that’s not possible, they bring in the highest quality items from local coastal or organic farms. The culinary team crafts a menu with diverse textures, flavors, and preparations, making the experience as unique as it is delicious.

Honestly, our experience at Soter is hard to fully explain. We were seated at a large table overlooking the valley, with wine glasses, a tasting book, and information about the wines we’d be tasting placed in front of us. The food, the wines, and our host were all exceptional. We enjoyed it so much that we signed up for their wine club and can’t wait for the wines to start arriving, just to relive the experience again.

Stop 2: Knudsen Vineyards

Next, we made a quick stop at Knudsen Vineyards. The tasting room was smaller, and while the wines were good, they didn’t quite match the exceptional experience we had at Soter. We did a walk-in tasting with no reservation for $35.

Stop 3: Domaine Drouhin - which quickly became another favorite! Domaine Drouhin is a renowned winery with a rich history in the Oregon wine country. Established by the Drouhin family, who have been making wine in Burgundy, France, for generations, the estate combines Old World expertise with New World innovation.

The tasting room at Domaine Drouhin offers a refined yet welcoming experience. Set against the backdrop of rolling hills and lush vineyards, the views are stunning. The winery is known for its exceptional Pinot Noir and Chardonnay, crafted with the same meticulous care that defines their Burgundy wines.

Visitors can enjoy guided tastings that highlight the winery’s signature wines and often include insights into their winemaking process. The ambiance is elegant, and the staff is knowledgeable, providing a deep dive into the wine's characteristics and the estate's history. It’s a place where you can appreciate the depth of flavor and craftsmanship in each glass, making it a standout stop in Oregon’s wine country.

We did The Drouhin Oregon Experience at Domaine Drouhin. For $40 per person, this experience showcased their 100% Estate cuvées from the Dundee and Eola-Amity Hills sub-appellations. We also enjoyed a delicious charcuterie board which we pre-ordered knowing we'd need to keep our bellies full of food!

Final Stop: White Rose Estate

Our final stop on the wine tour was White Rose Estate. We opted for their seated tasting ($60 per person), and the experience was unforgettable. The breathtaking views and the chance to walk through part of their vineyards made it extra special. Their focus on creating wines that resonate emotionally gave our visit a personal touch, rounding out our wine journey beautifully. Amazing wines and delicious cappuccino and chocolates to end the day.

I'm sure you don't need me to tell you that after a quick bite to eat we crashed hard!

Day 7 - Coffee Stop at Flag & Wire then on our way to the coast we go! The weather by the way was absolutely beautiful cool morning air perfect for a light sweatshirt and 77 during the day.

On The Road Again ... After our yummy muffins and coffee we hit the road for the Oregon Coast. Our only plan was to go as far South as we could and slowly make our way back, spending the night in the Depo Bay area. The drive from McMinnville to the Coast is approximately 50 miles.

Arriving at the coast, we couldn’t resist pulling over a few times just to soak it all in—the vast, beautiful blue waters and rugged, rocky coastline were simply breathtaking. There’s something about it that just soothes my soul. We had our first of many whale sittings which left me feeling all giddy. Who knew?

Our first official stop was Cape Perpetua, home to the fascinating Devil’s Churn. Cape Perpetua is a stunning, forested headland that juts into the Pacific Ocean, offering an amazing blend of towering trees wrapped in coastal fog, powerful waves crashing against jagged rocks, and clear views that stretch for miles.

Devil’s Churn is a narrow, rocky inlet where the ocean puts on a wild show. We followed the trail down to the rocks and spent some time exploring, watching the waves crash and churn with an intensity that’s both mesmerizing and a little bit humbling.

Cape Perpetua is just a couple of miles from Yachats, and the visitor center there offers fantastic views of the ocean, whether you’re inside or out on the deck.

We continued our coastal adventure to the small town of Florence, just about 20 minutes away. Our destination? The Sea Lion Caves! Honestly, nothing could have prepared me for the magic of this place.

As we pulled into the parking lot, I could already feel the excitement building. You could hear the faint barks of the sea lions in the distance. Looking over the edge, we spotted our first group—about 60 sea lions lounging on a large rock, sunning themselves, and taking turns dipping in and out of the waves. It was incredible.

But the real magic happens inside. We bought our tickets and headed down into the cave. Sea Lion Caves is America’s largest sea cave and the year-round home of the Steller Sea Lion. These animals are wild and roam freely, so they’re not always inside the cave. In the winter, hundreds of them gather here, but as spring arrives, they move out to the rookery areas on the rock ledges for breeding and birthing, staying there through the summer. The experience was unforgettable.

Originally, visitors had to tackle a steep quarter-mile trail and 250 stairs to reach the cave, which was tough for many. To make it easier, an elevator was added in 1958. The engineers carefully timed the blasting of a 70-foot tunnel and the excavation of a 215-foot shaft to avoid disturbing the sea lions.

**I have to admit, the elevator ride and the caves made me feel a bit uneasy, I am claustrophobic and not the biggest fan of tight spaces.

Reservations are not needed.

Adults: $18.00 each, Seniors: $17.00 each, Children* Ages 5 to 12: $12.00 each, Children* Ages 4 and younger: FREE

Next stop? Yachats for lunch! We made our way to this charming small town and enjoyed a meal at the Yachats Underground Pub. The food was delicious, and the view was absolutely beautiful, overlooking the serene waters. Perfect spot to relax and take in the coastal vibes.

We stayed at The Inn at Otter Rock -

The Inn’s rooms are nestled among the trees on a lush hillside, offering stunning views of the Pacific Ocean. Depending on your room, you might gaze south toward Yaquina Head Lighthouse, take in the striking sight of Gull Rock, or look north toward Cape Foul Weather. The multi-level design of the Inn means that each level is connected by walking paths, accessible only by foot or service carts.

Every room is privately owned, so each one has its unique charm with a variety of furnishings. You might find extra seating, a desk, a small table with chairs, or cozy club chairs. All rooms feature a balcony equipped with a table and chairs, plus essentials like a mini refrigerator, microwave, and coffee maker. Our suite included a full kitchen.

Parking is near the main office, and the rooms are spread out over the hillside. Whether you choose to walk or catch a ride with the bell staff, getting to and from your room is easy and adds to the tranquil experience of staying here. We were only there for 1 night but had a two-bedroom suit for only $100 on hotels.com

We stopped at a local market and whipped up a delicious Italian dinner, paired with some amazing wine we’d picked up along our journey. We enjoyed our meal on the expansive patio, watching the sunset over the Pacific. It was a truly magical evening.

Day 8: Moving on Up The Coast

We woke early to savor every last bit of the stunning views. With a fresh cup of coffee, I headed down the hundreds of stairs to the water’s edge, where I spent the morning just 70 feet away from a pod of seals perched on the rocks. I could have stayed there for hours, watching them scoot around and enjoy the peaceful morning. That our building in the picture, is top middle!

After soaking in the seals at the Inn, we set out for Depoe Bay for a whale-watching adventure. You can't visit Oregon and skip seeing the whales! Our boat left at 10am, and we were on one of Dockside Charters’ fifty-foot Delta boats—perfect for spotting whales. Depoe Bay prides itself as the whale-watching capital of the Oregon Coast, and for good reason.

Whale watching is a year-round affair here, with peak times during the winter and spring migrations of the Grey Whale. Whether you're seeing them as they move from Alaska to Baja or heading back north, the experience is truly unforgettable. Dockside Charters, a veteran-owned and family-operated company, provided a fantastic trip. We booked the 1-hour adventure, reservations are required and tickets were only $30pp. Of course, we have hundreds of pics - here are a few favorites!

** Be sure to bring along a sweatshirt or you can buy one inside at the store!

We met a friendly seal in the marina while waiting for the tour - has to share him with you...

Our next adventure led us to the Oregon Dunes National Recreation Area. This stunning stretch of sand dunes, extending 40 miles from Florence to Coos Bay, is the largest coastal sand dune expanse in North America. Here, the dunes rise up to 500 feet, create scenic views with coastal lakes, blend into flat ocean beaches, and are home to diverse wildlife. The ever-shifting sand and dramatic landscapes made for a truly unique experience!

This was a last-minute addition to our itinerary. Unfortunately, it was pouring rain, so we didn’t get to fully appreciate the beauty of the dunes. However, we did enjoy watching several trucks getting stuck and buggies zipping by. There are tour operators offering buggy tours, so that’s definitely on our list for next time!

Next up Tillamook, Oregon

Tillamook, Oregon, is a charming small town nestled on the scenic Oregon Coast, known for its dairy products, particularly cheese. The town is famous for the Tillamook Cheese Factory, where you can take a self-guided tour to see the cheese-making process and sample a variety of delicious cheeses. The factory also features a café with tasty options like grilled cheese sandwiches and milkshakes made with Tillamook ice cream.

Beyond the cheese factory, Tillamook offers beautiful natural attractions, including nearby beaches and parks. The town is a great spot to explore coastal landscapes and enjoy fresh, locally sourced food. It’s a perfect stop for a taste of Oregon’s dairy heritage and a chance to soak in the charm of a quintessential small coastal town.

After lunch in Tillamook at an old-fashioned parlor that felt straight out of the past, we headed to the Tillamook Creamery—and wow, what a treat! It’s like Disneyland for dairy lovers! You’ll want to carve out plenty of time to explore everything. Don’t miss the ice cream flight—it's a must-do to sample a variety of their delicious flavors!

Next up was the famous Cannon Beach. The hour drive from Tillamook was absolutely breathtaking, with awe-inspiring coastal views all along the way. We stopped at several overlooks, and on a whim, we decided to explore a spot called Hug Point.

Hug Point was a fantastic find on our trip! As we strolled along the beach, we were amazed by the tide pools teeming with colorful sea creatures and the impressive sea-carved caves. The rock formations and cliffs, sculpted by the waves over time, created a dramatic and beautiful backdrop. It was the perfect spot for some impromptu exploration and photography. Just a tip—make sure to check the tide schedule before you go, as the sea can quickly cover parts of the beach.

Not knowing exactly what to expect, we decided to follow a group of travelers up the beach around these massive rock formations, even though I was a bit nervous about the tide. And boy, are we glad we did! After walking about a mile, we stumbled upon the most amazing cave. It was a fantastic little discovery that added a touch of magic to our day.

Next Stop- Cannon Beach

Pulling into Cannon Beach felt surreal—seeing that iconic rock formation emerging from the water was like stepping into a dream. We stayed at the Hallmark Beach Resort & Spa. Our room was a bit dated, but the view was unbeatable. Just steps from the beach and right in front of the rock, it made up for everything.

Cannon Beach is a charming coastal town known for its stunning natural beauty and iconic landmarks. The town is famous for its wide, sandy beaches and the impressive Haystack Rock, a 235-foot sea stack that stands majestically off the shore and is a key attraction in the area. The beach itself is a popular spot for beachcombing, picnicking, and simply taking in the breathtaking ocean views.

For dining, the Wayfarer Inn offers a fantastic experience with exceptional views of Haystack Rock. The restaurant’s location right on the beach makes it a perfect spot to enjoy a meal while soaking in the scenic beauty of the coast. Their menu features a variety of delicious options, often highlighting fresh, local ingredients.

After dinner, a visit to the Pelican Pub is a great way to unwind. Located along the beach, this pub offers a relaxed atmosphere and a selection of local craft beers and cocktails. The oceanfront views and cozy ambiance make it an ideal place to end a day of exploring the beautiful Cannon Beach area.

Day 8: Exploring Downton Cannon Beach and back to Portland we go for the last night of our adventure.

We hit the road again and made a quick detour to see the wreck of the Peter Iredale in Hammond, Oregon. It was an interesting sight, but honestly, it didn’t quite live up to expectations. The rusted remains of the ship are cool to see up close, but if you’re short on time, you might not miss much by skipping it.

En route we stumbled upon Camp 18 ... It was a fantastic stop along the way, offering a slice of Oregon’s history and nature. Located off Highway 26, it’s a rustic log lodge with a welcoming atmosphere. The site features an impressive collection of logging memorabilia and antique equipment, reflecting its history and the region’s logging heritage.

The grounds include a short, scenic hike that takes you through beautiful, forested areas. It’s a great way to stretch your legs and enjoy some fresh air. After your hike, you can enjoy a hearty meal at the lodge’s restaurant. The menu often includes classic comfort foods like hearty burgers, sandwiches, and delicious home-style dishes. The combination of the hike, the interesting historical displays, and the tasty food makes Camp 18 a memorable stop on your journey.

After loads of traffic getting back into Portland, we finally arrived at our final destination: the Kennedy School. This former elementary school turned boutique hotel was one of the coolest places we’ve ever stayed. The building retains its historic charm with vintage classroom doors, chalkboards, and original architectural details, creating a nostalgic atmosphere.

Each room is uniquely decorated, combining old-school elements with modern comforts. The hotel features several intriguing amenities, including a movie theater in the old gymnasium, a bar called the "Detention Room," and an on-site brewery. The spacious grounds offer a large, landscaped courtyard where we could unwind and enjoy the quirky, artistic decor. Staying at the Kennedy School felt like stepping into a creative blend of history and modern hospitality, making it a truly memorable part of our Portland adventure.

We enjoyed a delicious dinner outside, taking in the unique atmosphere of the Kennedy School's grounds. After our meal, we took a relaxing dip in the spa pool, which was a perfect way to unwind. Later, we had drinks in the Boiler Room, a cozy spot with a great vibe, and finished the evening with a nightcap in the Detention Room, soaking up the quirky charm of this one-of-a-kind hotel.

Highlights from the hotel...

Day 9: Heading home. With heavy hearts, we said goodbye to the Kennedy School and made our way to the airport, just a convenient 20-minute drive away. This trip was truly unforgettable—one of the best adventures in my book. We packed in so many of the things we love: exploring the great outdoors, hiking, savoring delicious food and craft beers, enjoying wine tastings, staying in unique hotels, and spending quality time together. Oregon, you’ve been incredible, we will be back!