4 Day Itinerary for Portland and the Oregon Coast

My 4-Day Itinerary for Portland and the Oregon Coast

I recently planned a four-day trip to Portland, Oregon, with the idea of immersing myself in the city's vibrant culture, food scene, and quirky attractions. However, as much as I enjoyed Portland, I found that 2 days had been enough for me to explore the city and I found myself craving more. So, with a burst of spontaneity , I decided to rent a car and explore the stunning Oregon coast. Here’s a rundown of my itinerary in Portland and the Oregon Coast.

Day 1: Portland Downtown

I had arrived early in the morning into Portland with a somewhat vague idea of what I wanted to see and do, so I dropped off my backpack at the Dossier Hotel and started wandering around. I started with a visit to Fried Egg I'm In Love, a popular food truck at the Pioneer Courthouse Square. Despite a moderately-sized line and a 30-minute wait for food-truck breakfast, the nice weather made it enjoyable to walk around the Courthouse Square.

After breakfast, I headed over to the Willamette River and stopped by Mills End Park, known as the “world’s smallest park.” Continuing along the Waterfront Park Trail, I made my way over to the Portland Saturday Market. This is where every Saturday from March through December, local artisans and vendors showcase their handmade goods, including unique jewelry, artwork, clothing, and home décor.

After enjoying the vibrant market atmosphere, I walked by Voodoo Doughnut. The line was huge, and since I had already tried their famous doughnuts in Denver, I decided to skip it. Instead, I spent some time wandering around Powell's City of Books, getting lost among the countless shelves and fascinating reads.

By midday, I checked into the hotel to refresh before heading out again. In the afternoon, I visited Pittock Mansion, which turned out to be one of my favorite spots in Portland! The history and luxury of the mansion was incredible, and the views from the property were simply amazing.

In the evening, I went to Tope for some drinks, enjoying the lively rooftop bar atmosphere. I ended the night at the Coffin Club, a quirky and fun venue that perfectly captured Portland's eclectic vibe. It took a while for the club to become busy, but the drinks were cheap and it was fun to explore the unique venue. After the club, I took a short walk over to see the iconic Portland Oregon Old Town sign, wrapping up my first day in the city.

Day 2: More Portland Adventures

My second day in Portland started with a yummy breakfast at Saint Honoré Bakery, where I tried their classic Saint Honoré pastry. The bakery's cozy vibe and tasty treats made for a perfect start to the day.

After breakfast, I headed to Witch's Castle. Despite its name, it’s not a real castle, but the hike through the forest and lush Oregon nature quickly made it one of my favorite things to do in Portland. The peaceful, green surroundings were incredibly refreshing, and the hike was a fun adventure.

In the afternoon, I explored the Concordia neighborhood and visited McMenamins Kennedy School, an old elementary school turned into a hotel, brewery, theater, and more. This place is so unique and easily one of my top three experiences in the city. Walking through the hallways lined with student artwork and discovering the many hidden bars and cozy spots was truly fascinating.

Afterwards, I strolled along Alberta Street, a vibrant area with an eclectic mix of shops and galleries. I couldn’t resist stopping at Salt & Straw for some of their famous ice cream – the perfect treat on a sunny day.

In the evening, I went back to the hotel to relax with a few drinks and get some rest. Reflecting on the last two day’s I knew I needed to find something different to spend the rest of my time in Oregon.

Day 3: Hitting the Road to the Oregon Coast

By the third day, I had seen enough of Portland and felt like I needed a change of scenery. Walking around the city, it felt like I was seeing the same things over and over again. I decided to go on a road trip, so I rented a car and set off for Astoria in the foggy, rainy weather.

I started my morning with breakfast at Blue Scorcher Bakery & Cafe in Astoria, a cozy spot with delicious pastries and coffee. From there, I visited the Wreck of the Peter Iredale at Fort Stevens State Park. The rusted remains of the shipwreck against the foggy backdrop were hauntingly beautiful.

Next, I drove to Cannon Beach, where it was so windy and foggy that I could barely see Haystack Rock. Despite the weather, the rugged coastline was stunning. I made several stops at scenic viewpoints along the way, each offering a unique and breathtaking view of the Oregon coast.

I continued my journey to Tillamook, where I had lunch at Kitty’s Food and Spirits. The warm, hearty meal was just what I needed after the chilly coastal drive. After lunch, I set off for Newport and treated myself to some clam chowder at Ocean Bleu Seafoods at Gino's. It was the perfect dish to enjoy on a rainy day.

I managed to make it to the Oregon Coast Aquarium just in time to explore the exhibits, however, the visit to the aquarium wasn’t very eventful and I would recommend choosing a different activity if you’re short on time in Newport.

Day 4: Multnomah Falls and the Columbia River Gorge

My final day started with a drive to Multnomah Falls, one of Oregon’s most iconic natural landmarks. The drive through the Columbia River Gorge was breathtaking, with waterfalls cascading down the cliffs at nearly every turn. Multnomah Falls itself was a sight to behold, and I spent some time hiking to the bridge for an up-close view.

The rest of the morning was spent leisurely exploring the gorge, stopping at several other falls and viewpoints along the way. The fall colors were in full swing, adding a vibrant backdrop to the already stunning scenery. By noon, I made my way back to Portland to return the car and wrap up my trip.

Final Thoughts

What started as a four-day city trip turned into a spontaneous road trip with amazing landscapes and unforgettable scenery. Portland was cool and quirky, but I wouldn’t recommend anything longer than a weekend stay for those who are more antsy and looking for a bigger adventure.

I think 2 days in the city is the perfect amount of time to see the sights in Portland, however, as with most destinations, you might need a few weeks to get a feel for what it is to be a local. I definitely recommend driving the Oregon coast, as I saw some of the most beautiful landscapes I’ve ever seen on this road trip. The mix of foggy forests, dramatic coastlines, and awesome waterfalls made for a great adventure. If you ever find yourself in Portland with a few days to spare, definitely hit the road and check out the beautiful nature Oregon has to offer.