Oregon Road Trip | Exciting 7-day Itinerary for your First Visit

My friend and I picked a week of vacation before picking the destination. This is a great way to find cheap flights! The cheapest flights we could find (that weren’t places we’d been before) were from Ottawa to Portland, Oregon. My friend had heard great things so we booked our flights without planning the trip. The top comment I heard before going when I told people I was heading to Oregon was “Why Oregon? What’s in Oregon?”. I really cannot express how beautiful and wonderful the state was, and you’ll see “Why Oregon” throughout this post! Oregon is the ninth largest state, home of the first scenic highway in the US, has 6,000 lakes, 30 million acres of forest, 238 known waterfalls, 16 known hot springs, 750 vineyards, home of the tater tots, and so much more. You can find mountains, canyons, the ocean, rivers, lakes, arid plains, and everything in between on this Oregon Road Trip. There’s something for everyone!

I will preface this post with the obvious: there is SO much to do in Oregon, you can’t do it all in one week! This post focuses on the northwest quadrant of the state. Even with that, we covered a few things a day and there’s so many wonderful places to stop.

Where to Stay on an Oregon Road Trip

I highly recommend moving around on this road trip, rather than setting up in one place. There is so much to see, so save time by staying close to your end of day/beginning of next day activities. We booked last minute Airbnbs. So we were able to get last minute discounts, like no cleaning fees, no minimum stay lengths, and discounted nights. We probably saved a few hundred dollars each! We booked Airbnbs that were close to our road trip route, and interesting to stay at! I also recommend searching by number of beds – you may not want to share a bed!

You could definitely stay in the cities and venture from there, but I recommend the Airbnb/camping route. Portland, Salem and Eugene are essentially in a north-south line inland, and there are plenty of spots along the coast for day 1. I found that hotels were available in the cities, and there are plenty of Airbnbs and camp sites outside the cities and closer to the daily activities we did.

When to Visit Oregon

I’m sure Oregon is beautiful year round, but spring and fall are probably the best. After the winter snow melts, the waterfalls are peak flow in the spring. Some waterfalls dry up, or go down to a small trickle, by the end of spring. Fall brings beautiful red, yellow and orange fall foliage across the state. Summer would be luscious and green, but the more popular hikes and waterfalls are much busier. However, it’s always worth it to hike and visit new places so if summer works best for you, that’s the best too!

Oregon Road Trip – Suggested Stops

Oregon Coast

You could easily do an entire Oregon Road Trip along the coastline (see map above). For this Oregon Road Trip, there’s three stops in one day before heading back inland. The map above includes more stops along the coast. When travelling from one stop to another, check that Google Maps is taking you along the scenic drive rather than the highway. You’ll be blessed with plenty of wonderful views and stops along the way.

Ecola State Park

Heading from Portland straight to the coast, you’ll find Ecola State Park. There’s a few wonderful stops within this park, but head to the Ecola State Park Viewpoint. You’ll have to purchase a day pass to use the parking lot (cost is per vehicle). If you’ve arrived earlier in the day, you can do one of five hikes, walking along the beach, or grab a picnic to enjoy the views. The views below are about a 3-5 minute walk down a path to a lookout point. You can even spot Haystack Rock in the background!

Cannon Beach

The iconic Haystack Rock can be seen easily from Cannon Beach. At low tide, you can walk right up to it! There’s a whole variety of birds that collect on this rock, making it perfect for bird watchers. You might even spot the Tufted Puffin! You can find parking around the village, with multiple accesses down through the dunes to the beach. You’ll find people walking, playing beach volleyball and soccer, taking photos, and enjoying the beach. Mo’s Seafood and Chowder is a highly recommended restaurant along the coast, with one in Cannon Beach. Pelican Brewery is also a great spot to stop for a drink and some grub.

Pacific City Beach/Cape Kiwanda

Depending on your timing, head to Pacific City Beach for sunset. The less iconic Chief Kiwanda Rock still offers a stunning photo op along the beach. The Cape Kiwanda State Natural Area lines this side of the coast. The sandstone headland (photo below on the right) also offers an amazing view of the ocean and beach. You may even spot a kite flyer or two on this beach! Tillamook County operates the parking lot on either side of Hungry Harbor Road and charges a $10 Day Use Access Pass to park.

Where to Sleep Day 1: We ended up staying in Salem at a hotel, to be close to the Silver Falls State Park for a hike the next morning. It’s almost a straight line east, but on windy roads (not a highway). If you’re uncomfortable driving at night, I’d give yourself time to drive this route in the daylight. By the time we were done for the day, we had no cell service and just booked something easy to get to. However, there are plenty of spots along the coast, like in Pacific City (a little beach town).

Silver Falls State Park Trail of Ten Falls

No Oregon Road Trip would be complete without this hike. After grabbing breakfast in Salem, and packing a lunch, head to the South Falls Day Use Area in Silver Falls State Park. The Trail of Ten Falls is in Silver Falls State Park in northeast Oregon. As the name suggests, it’s a hiking trail with 10 waterfalls. Four of the ten waterfalls you can walk behind! There are four trailheads with the full loop being 7.2 miles (11.5 km) round trip. If you’re not up for the full hike, there are a few smaller loops to see most of the falls. It’s a relatively flat hike, with 800 m elevation gain total. It took us about 4-5 hours to see all 10 waterfalls, stop for a lunch break, and take a lot of photos. The South Falls Day-use Area has a café, gift shop, and restrooms, and is a great starting point. There is a small fee ($5USD per vehicle) for the day use parking lots.

Read More: Trail of Ten Falls | Full Guide with Photos

Where to Sleep Day 2: We found an Airbnb in Eugene, to be close to Day 3 activities. You’ll head almost straight south from Silver Falls State Park. Eugene is lovely, with plenty of accommodation and food options. I recommend picking up road trip food and snacks at the Market of Choice (a family owned grocer). If you’re from Ontario, it reminds me of Farm Boy.

Aloft Eugene Airbnb

Chasing Waterfalls – Toketee, Proxy, Spirit, Moon

Spend a day chasing waterfalls with this Oregon Road Trip! Toketee Falls was relatively easy to get to, with good roads. Moon Falls, Spirit Falls and Proxy Falls are close to each other. We did not get to see Proxy Falls, as the way was blocked by a tree that fell across the road. While Spirit Falls and Moon Falls are both very impressive, you get to them by a mountain road; one of the last roads to be cleared of any debris from storms. It took us almost double the time to get to the highway because we kept stopping to clear branches that hadn’t been cleared yet. If you’re visiting later in the year, it may be completed cleared for you! Keep this in mind if there’s been a recent storm or you’re visiting earlier in the year.

Toketee Falls and Heart Shaped Pothole

Toketee Falls is 113 m tall waterfall that cascades through basal columns into a blue pool below. The state has built a viewing platform to see the falls, and you can no longer go down to the water. On the way, there’s a heart shaped pothole. Parking is available at a small lot, and since the waterfall is a bit of a drive to get to, it’s really not that busy! It’s a short hike from the parking lot to the waterfall, and back.

If you search on social media, there are a ton of photos from years ago of people at the pool in front of the falls. However, the viewing platform is fenced for a reason: there have been a number of serious injuries and fatalities of people trying to get down to the pool of water.

Spirit Falls

Spirit Falls is accessible by a few switchbacks in along a fairy tale-esque trail to this magical waterfall. It takes about 20 minutes to get from the road to the waterfall. There’s maybe 2-3 spots available to park by the road, and no fee to access this waterfall. Similar to Toketee Falls and Moon Falls, they are further from civilization and therefore not nearly as busy as some other locations in Oregon. You’ll likely get this waterfall all to yourself!

Moon Falls

The final stop of the day is Moon Falls. We almost didn’t make it because the sun was setting and we couldn’t remember how far it was from the parking lot to the falls. Luckily, it’s less than 1 km and relatively easy to get to. That’s what makes this day so great: you can start later in the day and with the short hikes, see three incredible waterfalls!

Where to Sleep Day 3: I highly recommend finding an Airbnb or campsite in the country. Day 4 starts at the hot springs, so it’s a bit of a trek to stay in Eugene again.

Tiny Home in Springfield

Hot Springs, Blue Pool Hike and Natural Arch

Terwilliger Hot Springs

There are 16 known hot springs in Oregon. We picked the Terwilliger Hot Springs because it was on our way to other places on our itinerary. The Breitenbush Hot Springs was a close second for a visit. The Terwilliger Hot Springs has a few parking spots, and a ranger monitors the lot to make sure people pay the $10/person fee. It is a clothing optional hot spring. There are 4 pools, the top is the hottest and the bottom is the coolest. Unfortunately, a forest fire burned the lush forest that used to surround this hot spring, but it’s still a wonderful spot to visit and relax.

Two things to keep in mind when you visit. 1) the rocks can be slippery. We saw a woman slip in the pool and scrape her entire back. 2) The road to the hot spring is not winter maintained, so you may not be able to get there from about November to April.

Tamolitch Falls (Blue Pool)

While the name suggests a waterfall, unfortunately it dried up years ago! Sometimes there’s a waterfall after a big storm event or in early spring, but otherwise it’s just this beautiful blue pool of water. The photos really do show how blue and clear the water is: it’s barely edited in both these photos and really is this blue in person! It looks like the same colour as the Clear Lake, where this water comes from. The pool is actually fed by underground springs, which makes the water so clear. It’s a moderately challenging 3.9-mile out-and-back trail. You can swim in the pool, but with an asterisk.

Swimming is not prohibited, but it comes with a few major safety considerations. You can cliff jump into the pool; however, you must be careful of the rocks both on the cliff and in the pool. Some people have not jumped far enough out, or the water wasn’t deep enough where they jumped, which resulted in serious injuries or fatalities. The most concerning though is the water temperature. The average water temperature is 37°F (2.8°C). You must cool down after the hike in, as it’s a huge shock to the body to go from a hiking temperature to the water temperature.

Natural Arch Hike

I need to recommend this with a warning. The drive up is treacherous, rocky and bumpy so a low vehicle/sedan is not recommended. The hike is also steep with loose rocks (scree). The difficulty rating is “easy” on many blogs, but that may be for more seasoned hikers. I really cannot understate how steep the trail down is. A 2020 fire also decimated the area and burned all the trees. However, the natural arch is beautiful and frames the local mountains perfectly.

Where to Sleep Day 4: Head to Salem or Eugene for a relaxing day exploring a small Oregon city! We stayed at an A Frame in Woodburn, close to the Wooden Shoe Tulip Farm. It was peaceful, spacious, and a fantastic place to rest. You may want to book this place for 2 nights, to have a full day at the Airbnb for a relaxing day.

A Frame Cabin

Small City Exploring

After a few days of hiking and exploring the outdoors, you may need a day of rest. (We did!) You could book an Airbnb for 2 nights and stick around your accommodations. Or, take a day to visit one of the small cities in the area. Either way, this Oregon Road Trip includes stops in Eugene and Salem.

Wooden Shoe Tulip Farm

If you are travelling to Oregon in April, stop by the Wooden Shoe Tulip Farm. Not only do they have millions of tulips planted, they also have hot air balloon rides (weather permitting)! They have tethered hot air balloon rides throughout the day, or sunrise rides. When the balloons lift off, the photo opportunities are amazing! There’s also food trucks, carnival rides, a market, wooden shoe making demonstrations, and more!

Note: hot air balloon rides are very dependent on the weather. It cannot be raining and the wind speeds must be under 8 miles/h. However, it is still a beautiful farm and worth a visit rain, or shine! Rainy days make for beautiful moody shots.

Salem

When visiting Oregon, many people and blogs recommend food trucks. I’m not a huge food truck person (it’s never my go-to) but I highly recommend visiting the food truck squares around the state. The Yard in Salem is great. There’s plenty of food trucks, places to sit, an inside bar, and an outdoor play ground with corn toss and other games. Some other places to visit in Salem are the Riverfront Carousel, Adelman Peony Gardens, or Schreiner’s Iris Gardens.

Eugene

Eugene is a hidden gem. I didn’t see much about either Eugene or Salem when looking at Oregon blog posts. I found that Oregon in general is a quirky and fun state, surrounded by natural beauty. If you’re taking a day in Eugene, you can bike the Ruth Bascom Riverbank Path System, walk Through the Owen Rose Garden, visit the Jordan Schnitzer Museum of Art, go wine tasting, or shop at the Eugene Saturday Market.

Where to Sleep Day 5: You could stay in Salem or Eugene for a second night, to have a full day at your airbnb (or hotel if that’s what you choose).

Buena Vista Guest House

Columbia River Gorge National Scenic Area

Multnomah Falls

I’ve seen Multnomah Falls on social media for years, but never looked into where it was. I got it in my head that it was hard to hike to, and not somewhere I would get to see for a long time. Little did I know, it’s located just off the side of the highway with a huge viewing platform, and about 30 minutes from downtown Portland. Typically, it’s incredibly busy and hard to find parking. We lucked out by visiting on a rainy day, found lots of parking on the north side of the highway, and had plenty of opportunities to take photos and enjoy the hike up. Since the waterfall is so accessible, it’s best to visit early in the day or later in the evening to avoid the huge crowds. Also, don’t be discouraged if it’s raining! Moody, rainy days are some of the best for photography.

Punch Bowl Falls – Tunnel Falls

The Tunnel Falls hike is a long, challenging hike. It’s 12.2-mile out-and-back trail, so takes about 6-7 hours to do. Tunnel Falls is a waterfall you can walk behind, and looks beautiful! If you’re up for the hike, it definitely looks worth it. However, the shorter trek to Punch Bowl Falls is a stop along the way to Tunnel Falls. It’s only a 3.8-mile out-and-back hike and much easier than the longer Tunnel Falls trek. The views along the trail are stunning!

Where to Sleep Day 6: Head to Portland for the evening after chasing waterfalls in the morning! This was my favourite Airbnb of the trip: a speakeasy themed basement apartment! It comfortably sleeps 4 people, cocktail ingredients are provided (including non-alcohol ingredients), and is in a wonderful location in Portland.

Portland Speakeasy

Portland

You can start or end your Oregon Road Trip in Portland. While I’ve been loving trips with more outdoor activities and hiking, I loved the City of Portland. It’s an artsy, eccentric city with someone for everyone. From parks and bicycle paths, microbreweries, coffeehouses, delicious food trucks, fantastic cocktail bars, art, theatre and music scenes, and more!

Head into downtown, and find the Travel Portland ‘Near Me Now’ sidewalk cling (you can also download the app). It’s the City’s initiative to support local businesses and art. You can find everything from restaurants, murals, small businesses, bars, parks, theatres and everything in between. Each location also has a description, photo and address. For example, you can find murals on the map and a description of the significance and artist.

I’m working on a separate blog post for Portland, but some of my highlights were: Tea Flight at Smith Teamaker, Powell’s Books (world’s largest new and used bookstore), world’s smallest park (Mill Ends Park), and the Night Market.

Where to Sleep Day 7: Depending on your plans, you could spend a second night in the Portland speakeasy, or at the The Royal Sonesta Portland. Like most things in Portland, it was a quirky and fun hotel in downtown. It’s a perfect place to end this Oregon Road Trip.

The Royal Sonesta Portland