Updated: September 21, 2026
My Oregon road trip was only five days long, and let me tell ya, that’s barely enough time to scratch the surface of just how beautiful this state is.
But if you plan well and get your ducks and reservations in a row, you can cover a surprising number of stops without spending your entire trip in the car. In five days, I made my way from Portland to the Oregon Coast, over to Mt. Hood, and all the way down to wine country.
If you’re planning an Oregon road trip and want to see a lot without attempting to conquer the entire state in one trip, here’s exactly how I made it work and the 7 stops you shouldn’t skip.
My Northern Oregon Road Trip
Oregon has waterfalls, mountains, vineyards, life-changing cafes, and somehow they’re all within driving distance of each other. At one point, I genuinely wondered why I live in Illinois.
This itinerary focuses on Northern Oregon, which made it possible to pack a lot into five days. It’s definitely not an “I’ve seen it all!” itinerary, but it’s a great start. I already know I’ll need several return trips.
Map is clickable for general route 
These are the 7 stops you shouldn’t skip on your Oregon road trip.
Stop 1: Portland, for the best coffee scene around
Stop 2: Columbia River Gorge, for numerous waterfalls
Stop 3: Northern Oregon Coast, for scenic views and famous beaches
Stop 4: Hood River Fruit Loop, for the coolest farm experiences
Stop 5: Trillium Lake, for inspiring views without the hike
Stop 6: Mt. Hood/Timberline Lodge, for endless photo opportunities
Stop 7: Willamette Valley, hello amazing wine
1. PORTLAND, OREGON
I started my trip in Portland, the obvious starting point since I flew into the city. We arrived early enough to grab coffee at Slow Haste, where we had one of the best lattes we’ve had to date. Important side note: if you love a good latte, put Portland at the tippy top of your list.
Where to stay in Portland: I chose convenience and quiet over staying in the city, so I booked EVEN Hotel Beaverton. The rooms were spacious and super clean, and we were a short drive from everything.
I’m not a “hit all the attractions” type of traveler, especially on Day 1 of a trip, so instead I picked a few quirky things that sounded fun, grabbed dinner, and called it a day.
One stop was the popular Wishing Tree, a really cool community art project where strangers hang handwritten “wishes”. Rumor has it that if the note falls off, that means the wish came true. We went to the second location at 4048 N Williams Ave, which has expanded from a tree to a patio. But you can find the original tree at 2954 NE 7th Ave. I love this whimsical idea.
I also love ridiculous things, like visiting the world’s smallest park, Mill Ends Park. This tiny park is listed in the Guinness Book of World Records. It has one tree and measures 2 feet across. And yes, I ran around it. Obviously.
We also used day 1 to visit Multnomah Falls (below), since it’s only about 30 minutes away from Portland, and I wanted to leave the other days open for further stops.
If I had more time, I would’ve done a city tour to learn about the neighborhoods and see more attractions, like the view from the Pittock Mansion. I also would’ve loved to explore their boutiques, local goods, and vintage shops. All the more reason to return.
Portland Favorites I’d Fly Back For
• Slow Haste Coffee– Became one of our favorites ever.
• Never Coffee– Cool concept that combines colors with flavor profiles.
• No Preference Coffee– Delicious and well-balanced.
• Little Griddle– Great breakfast; we went twice.
• Bastion PDX– Amazing breakfast and lunch bowls. Good option if your belly needs some love.
• Doe Donuts– Vegan, fluffy, and full of flavor.
• Grana– Great Neapolitan pizza.
• Scotch Lodge– Beautiful bar with delicious cocktails that just won a James Beard award.
A Slow Haste Latte 🥹
Bastion PDX goodness
Our Grana pizzas
Quirky receipts from Little Griddle
2. COLUMBIA GORGE WATERFALLS
From Portland, I headed toward the Columbia River Gorge. This is one of those times in Oregon when you think, dang, the main city is just down the road from this?!
The Gorge is home to several waterfalls, but with only five days for this road trip, I knew I couldn’t see them all. We ended up visiting the most popular and easiest one to get to, Multnomah Falls. As expected, the waterfall is impressive, and I especially loved that I didn’t have to hike to see its grandeur.
If you have more time than I did, I’d add a few more waterfalls to your itinerary that require little to no hiking, including:
- Latourell Falls
- Horsetail Falls
- Bridal Veil Falls
- Wahkeena Falls
TIP: You may need a timed permit for Multnomah Falls if you’re visiting during peak summer season and using their parking lot. It’s a few dollars and easy to buy online. When we parked, an attendant asked for our permit. We showed it from our phone, and we were on our way.
3. CANNON BEACH ON THE NORTHERN OREGON COAST
Famous for a lot of things, this Northern Oregon Coast drive is highly recommended by most. And if you’ve seen photos of Oregon’s coastline, you probably already know where we were headed: Cannon Beach.
Haystack Rock is the star of the show here, but I think the entire drive along the coast deserves attention. I planned a full-day trip starting at Tillamook Creamery (try the marionberry ice cream; it’s a local fruit) and going all the way up to Astoria for fish and chips. That route is only 1.5 hours long, but it took us about 6 hours.
If you have an extra day, I’d consider slowing down and spending more time along the coast.
I’d love to explore more of the central cities and head south. My main goal would be to capture more landscapes and try to find sea lions, whales, and seals. I read that they’re abundant along the coast during certain seasons.
If I could plan this route again, I’d dedicate one day to driving from Lincoln City to Florence along the coast. I absolutely would’ve stopped at Depoe Bay, a place known for whale watching.
4. Drive the Hood River Fruit Loop
I can confidently say this has become one of my favorite drives in the US. The Hood River Fruit Loop (I love the name) winds through the Hood River Valley, where farms, orchards, wineries and flower fields are basically competing for the prettiest view. And everywhere I looked, Mount Hood (a dormant volcano) was photobombing the landscape.
One place I definitely recommend adding to your list is Hood River Lavender Farm. The combination of lush lavender fields, vineyards, and Mt. Hood views made it one of my favorite photo stops of the trip.
And don’t just drive from Point A to Point B. Stop at the farms that catch your eye. Pick up some local products, grab some lavender ice cream, take photos and enjoy the sights. That’s really the whole point of the Fruit Loop. I’m using a lavender heat wrap that I bought during that drive as I type this.
When to visit: The Hood River Fruit Loop changes with the seasons, so check individual farm hours and what’s in season before you go. This is how it looks in July ↓
TIP: If you’re starting in Hood River and love BBQ, stop at Grasslands Barbecue for lunch. It’s a popular food truck serving up Texas-style BBQ. They have long lines, are only open on weekends, and are closed in the winter, but if you’re around when they’re open, check them out.
5. Trillium Lake (One of the Best Mt. Hood Views)
I can’t stop swooning over the photos I took of Trillium Lake. Not because they’re phenomenal, but because this place looks unreal.
I wanted that classic Oregon mountain-and-lake scenery without having to work too hard for it, so I added Trillium Lake to my list. And I’m so glad we didn’t miss it. It’s an easy stop along the Mt. Hood Scenic Byway (more on that next).
Trillium Lake offers one of the best Mt. Hood views. The lake sits with Mt. Hood towering behind it, and the whole scene is spectacular. You can swim, rent a kayak, hang out by the water, or just enjoy the scenery. It’s a pet-friendly, kid-friendly stop.
TIP: Depending on the season, you may have to wait in a car queue to get into the nearest parking lot. It goes pretty quickly. You can also park in the exterior parking lot, but you’d need to take a shuttle bus to the lake, and it costs several dollars each way. If you drive into the nearest parking lot, you’ll have to pay for a parking pass. Either way, ya gotta pay.
I’m adding this photo below just to show you the difference between using a lens polarizer filter for your camera. The photo above has the filter, and the one below doesn’t. I feel like it makes the colors sharper and minimizes glare, all for $14. Obviously, better filters exist, but this is a good one if you’re starting out and want to test it in your photography. I’d especially use it for landscape photos.
6. Drive the Mt. Hood Scenic Byway to Timberline Lodge
The Mt. Hood Scenic Byway is a 105-mile drive that starts (or ends) near Hood River and Troutdale. On a clear day, you’ll see the Mt. Hood volcano popping up at different viewpoints.
If it’s an exceptionally clear day (as we had in early July), you could also see Mount Adams or even Mount Rainier over in Washington.
During the drive, you can stop at several viewpoints, including Jonsrud Viewpoint and Barlow Pass, a historic stop with ties to the Oregon Trail.
The drive is beautiful, but once the road starts leading up to Timberline Lodge, you can almost touch Mt. Hood! You don’t need to be a serious hiker to enjoy this stop. For me, the drive and the views were the attraction.
TIP: A visitor parking lot is a short walk from the lodge. Make sure you don’t park at the resort guest parking lot. You can explore the grounds, take photos of Mt. Hood from different angles, or check out their bar with a view.
Jonsrud Viewpoint ↓
7. WILLAMETTE VALLEY FOR WINE TASTINGS
And then there’s wine? As if Oregon wasn’t already showing off, you can find over 700 wineries in Oregon’s Willamette Valley wine country. You’ll also find some of the best Pinot Noir outside of France in this region. After visiting, I completely understand Willamette’s strong reputation.
You will need reservations for most wineries, as they’re family-owned small businesses. However, some are open to walk-ins for a glass of wine or possibly a tasting, depending on how busy they are.
We booked a tasting at Six Peaks Winery and Cristom Vineyards. And we walked in for a glass at CHO Wines and Hawks View Winery. All of our experiences were great. Our favorite was Cristom. I also had Domaine Roy & Fils, Resonance Wines, and Bryn Mawr Vineyards on the list for next time.
Make time to explore some of the cute towns in the area, like McMinnville.
View from Six Peaks ↓ On a clear day, you could see Mt. Hood.
CHO Wines has a lovely winery ↓
My husband enjoying our tasting at Cristom ↓
Willamette Favorites
Loam Kitchen– Great farm-to-table breakfast.
Caravan Coffee– Delicious coffee in Newberg.
Where to stay in Willamette Valley: I chose Fairfield Inn in Newberg to explore the wine country. We were near tons of wineries, had free parking and clean rooms– what more can we ask for?
If you’d rather have someone handle the logistics, here is one of the best-rated tours I found in the region. It offers free cancellation up to 24 hours before the experience starts.
TIP: Willamette rhymes with dammit.
Now you can see why we’re so in love with this place. I wish we had time to see more, like visiting the only remaining Blockbuster in Bend OR or visiting Crater Lake National Park. I just know we have to go back.
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