Welcome to Oregon, a land of stunning natural beauty, vibrant cities, and world-class wine. If you’re planning a visit to the Pacific Northwest, Oregon should be at the top of your list. I recently had the pleasure of exploring this diverse and captivating state, and I’m excited to share my four-day itinerary with you. From the bustling streets of downtown Portland to the tranquil shores of the Oregon coast, this journey has something for everyone.
Day 1: Downtown Portland & Waterfall Hiking Day
My Oregon adventure began with an early morning flight to Portland, where I was whisked away from my everyday life and delivered to the City of Roses. The flight arrived around Noon, giving me plenty of time to make the most of my first day in the state.
After landing at Portland International Airport, I picked up my rental car and was on my way to the Moxy Marriott Downtown. The hotel’s location in downtown Portland proved to be ideal for exploring the city.
The plan for the day was to combine urban exploration with the natural beauty that Oregon is famous for. The Columbia River Gorge is home to several stunning waterfalls, and I couldn’t wait to experience them. Here’s what my day looked like:
- Multnomah Falls: A moderate hike, this 2.6-mile out-and-back trail will take you about 90 minutes to complete. While I didn’t make it to the very top, the lower viewpoint offers a breathtaking view of the falls. The drive along Highway 30 was incredibly scenic, connecting various hiking trails and waterfalls along the way.
- Ponytail Falls: This moderate 0.9-mile out-and-back hike, which takes approximately 35 minutes to complete, was well worth it. The trail leads to a beautiful waterfall, and the lush greenery surrounding it is a photographer’s dream. Known for the waterfall you can walk behind, this one is a must.
- Wahkeena Falls: Driving along the Historic Columbia River Hwy, you will encounter a multitude of waterfalls and hiking trails, and this is one stop that was not originally on my list, but I’m glad it caught my eye!
Additional options:
- Latourell Falls: I skipped this short and easy 0.2-mile out-and-back trail, opting for Wahkeena Falls instead. Both are delightful options for a quick stop.
- Wahclella Falls Trail: Though I didn’t get a chance to hike this trail, it’s a great option if you have extra time. It’s an easy 1.9-mile out-and-back trail that takes about an hour to complete.
By the time I finished hiking, I headed back to the hotel. But the day wasn’t over yet. I explored Downtown Portland and Pioneer Square, checking out iconic spots like the Portland Stag Sign and Powell’s Bookstore, one of the oldest used bookstores in the states.
For dinner, I dined at Dolly Olive, a local gem that didn’t disappoint and was only a short walk from my hotel. If you’re looking for alternatives, consider Portland City Grill for its amazing views or Janken for sushi.
Day 2: Willamette Valley Wine Day
With the city behind me, it was time to indulge in some of Oregon’s finest wines. I kicked off the day with breakfast at The Daily Feast in Downtown Portland, a local diner offering incredible service and a hearty start to a day of wine tasting. This diner was within walking distance to my hotel.
My journey took me to the renowned Willamette Valley, a region known for its exquisite Pinot Noirs. Here’s how my wine day unfolded:
- Alexana Winery: A scenic 60-minute drive took me to Alexana Winery, where I indulged in a $50 tasting experience and paired it with a $15 charcuterie platter. The combination of wine and delectable snacks was a match made in heaven. Make sure to book your tasting in advance.
- Red Hills Market: Just 10 minutes away from Alexana, this market was the perfect spot for lunch. It’s also conveniently located near Argyle Winery Tasting Room, which I didn’t have time to visit, but it’s highly recommended for sparkling wine enthusiasts.
- Patricia Green Cellars: My next stop was Patricia Green Cellars, located a 20-minute drive away. Here, I enjoyed another fantastic $50 tasting experience. Booking in advance is essential for this popular destination. I was greeted with a glass of rosé, and my tasting included 1 Sauvignon Blanc and 5 Pinot Noirs, finished with a bonus tasting of a select Pinot Noir. This stop was well worth it, and the vineyard views are incredible!
While there are hundreds of wineries to explore in this Valley, other recommendations from friends included Penner Ash, a woman-owned winery, and Willakenzie.
After a day filled with wine tastings and culinary delights, I headed to McMinnville to stay at The Boutique Retreat, a cute village of tiny homes! I absolutely loved my stay here, and when I return to Willamette Valley, I would definitely opt to stay here again. I took the opportunity to explore Downtown McMinnville and then grabbed dinner at Pizza Capo, which came highly recommended and understandably so. La Rambla also came recommended from friends, and locals suggested Humble Spirit and Cypress as excellent alternatives.
Day 3: Oregon Coast Beach Day
Day three was all about the dramatic beauty of the Oregon coast. After a filling breakfast in McMinnville, I hit the road for a day of exploration.
The stunning coastal landscapes awaited me, and here’s how I made the most of it:
- Cape Kiwanda: A one-hour drive from McMinnville brought me to Cape Kiwanda, where I embarked on a one-mile loop trail, taking about 30 minutes to complete. The breathtaking vistas and dramatic cliffs made this a must-visit location.
- Oceanside Beach State Park (The Tunnel): A 40-minute drive took me to Oceanside Beach State Park, home to the iconic tunnel. This beachside gem is perfect for a leisurely stroll, although, I’d highly recommend visiting when the tide is low, so that you can explore the tunnel.
- Tillamook Creamery: Cheese and ice cream lovers, this one’s for you! The Tillamook Creamery was a 20-minute drive away from Oceanside Beach State Park. You can opt for a self-guided tour, a $15 tour and tasting experience, or a more extensive tour. It’s an excellent opportunity to learn about the art of cheese-making and indulge in delicious samples. Of course I couldn’t leave Tillamook without a waffle cone – the white chocolate raspberry hit the spot for me!
- Oswald West State Park (Neahkahnie Viewpoint): An hour’s drive from Tillamook, Oswald West State Park’s Neahkahnie Viewpoint offers incredible vistas of the coastline. The lush forests and rugged cliffs make it a photographer’s paradise.
- Cannon Beach / Haystack Rock: A 10-minute drive brought me to Cannon Beach, home to the iconic Haystack Rock. I spent a great deal of time here, walking up and down the coastline. Nearby Ecola State Park also offers more stunning views and hiking opportunities.
I checked in to Tolovana Inn, where I opted for an oceanside studio. Watching the sunset and sunrise along the beach was the perfect end to my vacation!
Day 4: Travel Home
The final day of my Oregon adventure had arrived. I began my morning with a visit Oasis Cafe for coffee and Cannon Beach Bakery for sweet breakfast treats to fuel up for the journey home. A nearby popular option to locals is Sleepy Monk Coffee Roasters. I said goodbye to the Oregon Coast and headed back to Portland.
This four-day adventure in Oregon left me with lasting memories of stunning landscapes, delicious wines, and the warm hospitality of the Pacific Northwest. As a solo traveler, I felt safe and welcome by locals throughout my trip.
From the bustling city of Portland to the serene shores of the Oregon coast, this journey offered a diverse range of experiences that will linger in my heart for years to come. If you’re considering a trip to the PNW, I hope this Oregon travel guide inspires your own unforgettable adventure in this beautiful state.
