20 Stops Not To Miss!

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Raw. Weird. Wonderful. These are just a few of the terms you’d use to describe the rugged terrain and lifestyle of a state still in the process of defining itself. We spent 5 weeks on an Oregon road trip and had some incredible adventures.

Its snow-capped mountain peaks, towering forests, coastal scenery, thundering waterfalls, high desert spaces, and meandering rivers invite you to slow down, explore, and find solace in the beauty on of the Pacific Northwest.

Plan for a good amount of time as there are so many cool things to do in Oregon. It is full of adventure, beauty and plenty of good breweries! But if you’re not sure where to stop on your Oregon road trip, then read on to find out.

Below is our ultimate Oregon road trip itinerary, featuring stops we personally loved. Although we took 5 weeks to do this, you can pick and choose the stops that speak to you, and whittle it down to fit your time frame.

Oregon Road Trip Itinerary

Below are the best stops for Oregon adventures, starting and ending in Portland as this is the largest city in Oregon and an easy point to start from.

It’s on the border with Washington State, so you can extend this road trip into Washington as well if you have time.

You can see the route we took in the following interactive map:

Stop 1: Portland

Starting a road trip in Portland is a great way to get acquainted with the lifestyle and vibe of Oregon. As a city, it’s really easy going, and has a small town community feel.

Before hitting the open road, I recommend spending a day or two exploring Portland’s lively downtown, known for its independent coffee shops, craft breweries, and food truck scene.

Take a stroll through the Portland Japanese Garden, Washington Park, or the International Rose Test Garden on a sunny and warm day, or if it’s cold and rainy, head to the Portland Art Museum or browse the aisles of Powell’s City of Books, the world’s largest independent bookstore.

Portland’s location means you can easily reach the Oregon Coast next, or the historic Columbia River Highway, all within a few hours’ drive. We chose to visit the coast last, so headed inland to explore the beautiful forests and gorges there first.

Read more: Places to eat in Portland (and drink beer & coffee

Stop 2: Multnomah Falls Loop Hike, Columbia River Gorge

Multnomah Falls is a must see – it’s the most well-known waterfall in Oregon. This 611 ft. tall cascading waterfall is only 30 minutes from Portland and is the tallest waterfall in the state.

As it’s one of the most popular tourist attractions in the state, you probably want to include it on your Oregon road trip. The surrounding Columbia River Gorge region is stunning (and full of waterfalls), so be sure to explore more of this region beyond Multnomah Falls.

Skip joining the masses of people from the Benson Bridge, the observation point offering a perfect view of the first and second drop of the waterfall. Instead, take on the 5 mile loop walk to the waterfall. Not only will you experience the power of this gigantic waterfall from top, middle and bottom, but you’ll also pass by five other waterfalls along the way, as well as countless cascades.

Note: the beginning part of this walk is strenuous. You will climb 1,600 feet over a series of switchbacks.

Take your time, you’ll have a few waterfalls along the way that will help you catch your breath:

• Wahkeena Falls
• Fairy Falls
• Wiesandanger Falls
• Ecola Falls

Lemmons Lookout had the most stunning views out over the gorge. I also enjoyed walking through the blackened forest, which was still recovering from the 2017 fire at the time we visited.

Our tip is to start at the Wahkeena Trailhead, a short walk east of Multnomah Falls. On the way back down you’ll eventually hit the top of Multnomah Falls and have views of it on the many switchbacks leading back down.

You’ll be happy you’re going down as you pass by all the panting people walking up.

The kids will find this hike a challenge, but keep them going with promises of a delicious soft serve ice cream at the end. It’s the Multnomah way.

Read More: Highlights of the Columbia River Gorge: Multnomah Falls + Hood River Fruit Loop Drive

Video: Watch us explore the Columbia River Gorge region

Stop 3: Drive the Hood River Fruit Loop Trail, Columbia River Gorge

Moving onto Hood River, we spent a day driving the Hood River Fruit Loop Trail, which takes us to berry picking, wineries with stunning views of Mt Hood and Mt Adams, as well as cideries and lavender Farms.

Be prepared to sample delicious goods straight from the source including fruit, beer, wine and cider – all with the spectacular backdrop of snow capped Mt Hood and Mt Adams.

Both mountains face off from each other, you’ll get to see at least one of them no matter the direction you drive, and sometimes you’ll find a spot where you can look front and back to see both.

The Hood River Fruit Loop trail is a stunning 35-mile self-guided road trip through the fertile Hood River Valley. There are nearly 30 small, family owned  farms, orchards, cideries and wineries you can stop at along the way.

Many of the orchards offer u-pick opportunities including apples, pears. cherries, peaches, and berries. Some of our favorite spots on the Hood River Fruit Loop Trail:

Stop 4: Mount Hood National Forest

Mount Hood is a potentially active volcano in Oregon that is best known for its ski slopes and alpine winter sports. It’s the largest ski resort in Oregon and has 85 slopes that are suitable for all levels of skier.

Another attraction near Mount Hood is The Timberline Lodge. It’s famous for being the setting for the Stephen King movie remake of The Shining, though in the book the hotel was set in Colorado.

Though famous for the horror movie, it has been operating as a hotel for 80 years and is still family-run.

Stop 5: Misery Ridge Trail, Smith Rock State Park

Our good friends Mike and Ann from Honeytrek recommended the Misery Ridge Trail in Smith Rock State Park. They had previously come out with great suggestions such as the Peek-a-Boo and Spooky Canyon in Utah (the kids favorite hike ever), so we knew it was a good idea to listen to them. They were not wrong!

The Misery Ridge Trail is spectacular and definitely in my top 5 hikes in the United States. It was everything I love about a hike: heart pumping, a little challenging with periods of rest, diversity of landscape that just had your jaw dropping, and incredible views!

Smith Rock State Park is about 30 minutes north of Bend, and the Misery Ridge trail is the most popular trail in the park. It’s a 5.5 mile loop trail that begins with a steep climb up to the summit at 3,300 ft. There are switchbacks to make it easier, but it will be quite the exertion.

Take it slow and pause to catch your breath and admire the beautiful views of the Crooked River. It will be over in about 20 minutes and from then on the rest of the hike is easy.

You’ll walk along the ridge for awhile before coming back down and completing the walk along the river bank. The views and scenery are just spectacular.

Leave time to stop for awhile at Monkey Face, the huge free-standing pillar and one of the park’s icons. This is one of the most famous rock climbing walls in the country. You can watch climbers climb up to the monkey’s mouth.

The view from here was one of the most beautiful I have seen in the country. Be sure to spend time soaking it up.

The towering rock spires of Smith Rock State Park have been drawing rock climbers from around the world since the 80’s. You’ll see plenty of them, from the advanced Monkey Face scalers to beginners on the easy rock face walls as you walk back around the river.

Stop 6: Tubing the Deschutes River, Bend

Tubing on the Deschutes River in Bend was one of our favorite attractions in Oregon, especially on a hot summer’s day.

Unfortunately, we had a freak cold spell and jumped in the tube with the water temps at a chilly 57 degrees and the outside temps barely nudging 70. But we were determined not to miss out! Don’t let the cold stop you as we had a blast regardless. You get used to the cold pretty quick and the experience was relaxing and scenic.

What made the tubing in Bend a standout were the rapids at the Whitewater Park. This is where the river splits into three separate channels for all skill levels. Tubers will want to go down the Passageway Channel which is a more mellow series of rapids.

As you come down the rapids you can easily get stuck in them as it hits the water underneath on the next level. You may have to wait for another tube to bump you out of it if you can’t get yourself out.

Or, you could be just like me and flip out!

It was refreshing fun and I recommend going down them a couple of times as the kids did. You’ll definitely want to stay awhile and watch the surfers ride the waves in the whitewater channel next to the tubing one. It created distinct man-made waves you can surf or kayak through.

You can tube the river all the way into Drake Park in downtown, but we cut it short at the rapids because of the weather.

Read more: The best things to do in Bend Oregon

Video: Watch us explore Bend, Oregon

Stop 7: Lava River Cave, Bend

This was one of the most unexpected and fun Oregon adventures we had. I didn’t know much about Bend except for the river tubing and breweries, but when we arrived we discovered a really cool volcanic landscape and history to explore at the Newberry National Volcanic Monument, the largest volcano in the Cascade Range.

The Lava River Cave was formed 80,000 years ago with the Newbury Volcano’s eruptions and offers a mile-long lava tube, making it Oregon’s longest lava tube. The walk was a fun and unique self-guided hike on uneven ground in the dark.

Be prepared for slippery surfaces and 150 stairs. I nearly fell over loads of times as I had a very dim flashlight. The kids had a blast running ahead in the dark, and trying to spook each other by jumping out.

It’s 42°F degrees year round in here so be sure to wear warm clothes and sturdy closed in shoes. The tube narrows and shortens in some sections so watch your heard. Don’t forget your bright flashlight. Or you can hire them there.

Top tip: Go early as the parking lot here is small and gets full quickly.

Stop 8: Bike Ride to Benham Falls, Bend

The bike ride to Benham Falls was one of my favorite things to do on our Oregon road trip. The 5.5 miles (one way) bike path winds through pretty forest to the Deschutes River at the Benham Falls Trailhead.

We knew were were going to be in for a bit of a challenging ride back when the trail began going slightly downhill and pretty much stayed that way for the entire length of the ride. Oops.

Savannah nailed it and she had no gears and was on a small kids bike. I don’t know how she could peddle up those hills singing and chatting away to me.

Once you get to the Benham Falls Trailhead the path follows the river and is beautiful. Benham Falls is not a plummeting waterfall, but rather a series of cascading rapids with forest on either side.

It’s a beautiful sight and well worth the bike ride. You can also drive down to the falls if you don’t want to bike it.

Stop 9: Koosah & Sahalie Falls Hike, McKenzie River

A short, one way green forested trail meanders beside the pristine turquoise waters of the Mackenzie River taking you to two waterfalls: Koosah and Sahalie Falls.

The waterfall trail hike was my favorite of things to do in Mackenzie River area. Sahalie Falls is a mass of foaming white water plunging 100 feet (30 m) over a natural lava dam and Koosah Falls drops approximately 70 feet (21 m) into a deep pool.

You will find more parking at Koosah, so we began our hike from there. You can either hike directly by following the river, or there is a larger 3 mile loop walk going through the forest that takes in the two waterfalls.

We didn’t do this one, but I think the direct path along the river would be far prettier. The loop walk does not go beside the river, and that was the real highlight for me.

Don’t miss the McKenzie River Valley for stunning waterfalls, lakes, and hiking!

Video: Watch us explore the McKenzie River region

Stop 10: Willamette National Forest

The Willamette National Forest is a gorgeous region in central Oregon that has 380,000 acres of wilderness and includes seven mountain peaks of the Cascade Range. Some notable peaks are Mount Jefferson and the Calapooya Ridge.

The landscape is beautiful, with hiking trails, waterfalls, and rivers, the most famous is the Willamette River, which is where the park gets its name.

It is said to be home to some endangered species such as the northern spotted owl.

If you plan to visit the forest, we recommend staying in Eugene, which is a city with a lot to see and do.

Stop 11: Crater Lake National Park

We hesitated in taking the day trip from our camping spot in Umpqua National Forest to drive the hour to Crater Lake National Park. Would it really be worth it for just half a day? Yes. Yes. and more yes!

Crater Lake was worth it even though half of it was closed due to snow still covering the road. In fact, someone was skiing down the steep mountain when we arrived!

It meant we could not complete the full 33 mile loop road, nor do the Cleetwood Cove hike down to the lake (and take a refreshing dip), nor take a ferry ride out to Wizard Island, but that was okay.

We could still marvel at the dramatic volcanic scenery from various viewpoints and be stunned at the deep blue water with shades of turquoise color.

If you want more amazement, Crater Lake is the deepest lake in the USA and one of the most pristine on earth, its purity created by rain and snow filling in the caldera formed during a violent eruption 7,700 years ago.

July or August is the best time to visit Crater Lake when most things will be reopened. I highly recommend staying a bit longer if you can to do some of the activities mentioned above.

Crater Lake National Park is one of the most beautiful places to see in Oregon and will amaze you.

Video: Watch us hang out at Crater Lake

Stop 12: Ashland

Another popular stop on an Oregon road trip is Ashland in the southern region of Oregon. It’s an alpine town and has excellent ski facilities in the winter.

In the summer, these slopes turn into adrenaline-fueled mountain biking trails.

This stunning, and green city is surrounded by natural beauty. You’ll find plenty of hiking trails, especially in North Mountain Park which has a nature center and themed gardens. Lithia Park is also a stunning green space in the city worth visiting.

It’s also known to host the Oregon Shakespeare Festival. If you’re looking for a sleepy small town to relax in, Ashland is a great option.

Stop 13: Brookings

Brookings lies close to the California border on the Southern Oregon coast. It’s known for its scenic landscapes and music festivals.

It’s also a lot warmer in temperature than in other parts of Oregon. This is due to the airflow that parallels off the river basin. Some even refer to this as the “Brookings Effect.”

Along the coast, you’ll pass by incredible sea stack rock formations. The most famous of which are the Natural Bridges, which are located just a short hike from the road.

Another stop worth adding to your Oregon coast road trip is Secret Beach, which only appears during low tide. You’ll find the trailhead just north of Miller Creek on Highway 101.

If you’re looking for a stop on your road trip where you feel like you’re in a more tropical, Californian environment, then don’t rush past Brookings.

Stop 14: Quad Biking the Oregon Sand Dunes, Florence

What family wouldn’t love a thrilling ATV adventure? Well, hit the sand dunes in Florence and you’ll find miles of undulating dunes waiting for you to zip up and down – take your pick: your own quad bike, or a two or four person side by side.

The Oregon Dunes National Recreation Area area is a merging of forest, ocean, Siuslaw River, and desert that stretches south about 40 miles from Florence to Coos Bay on the Oregon South Coast.

The undulating dunes will stretch for miles and you could easily get lost amongst the drifts and drop offs. Be sure to be careful when you approach or you may get airborne!!

Kalyra and Craig did the individual quad bikes and Savannah and I did the ATV side by side from Torex ATV Rentals. 

We were concerned about Savannah going on her own and not being able to manage the brake. A few weeks before we were bike riding in San Francisco and she had a hand brake for the first time and struggled with it.

As our other friends had quad bikes, Knox (7 years) gave Savannah a little turn on the flats and she handled it really well. So she definitely could have done the quad bike.

This was a wild fun Oregon adventure zipping up and down the dunes. The kids had a blast and is a must on your Oregon Coast road trip.

Video: Watch us Quad Biking in Florence, OR

Stop 15: Tide Pooling near Yachats

I’d never really understood tide pooling until I was peering at rock walls covered with gooey globs of bright greens, purples and orange tessellated between bright orange starfish.

What is this world I have just discovered? Turns out tide pools are one of the top Oregon coast attractions and I wanted to play there all day. I guess the local tide pools at my Australian home didn’t know how to do it properly as I had no idea this was what you could find.

The kids had a blast discovering this underwater world that throughout the day is mostly covered by 3 feet or more of ocean water. There was all manner of weird and wobbly-shaped creatures of various sizes and vibrant colors.

There are tons of tide pools in that 180-mile stretch of the Oregon coast road trip from Florence up to Astoria that you can find and explore. Time your visit 1-2 hours before low tide so you have plenty of time to see the wonders.

We visited the tide pools near Thor’s Well just outside the small town of of Yachats. There is a 20 mile stretch of rocky basalt ledges near Yachats that brings abundant tide pools to explore.

The Oregon Pacific Coast Highway is on our best USA scenic road trips list.

Stop 16: Newport

Newport is basically the halfway point along the Oregon Coast. It’s where you’ll find the Yaquina Head Lighthouse, the tallest lighthouse in Oregon, and the Oregon Coast Aquarium.

This part of Oregon is thriving with local marine life, and is a great place to try some seafood.

You should also make sure to visit Yaquina Bay State Park, which is an area of outstanding natural beauty, and the Rocky Creek View Point.

Stop 17: Jet boating on the Rogue River, Gold Beach

One of the best adventures on your Oregon road trip is to spend a day jet boating on the wild and scenic Rogue River on the South Oregon Coast.

The girls will never forget this adventure squealing and waving their hands in the air with their friends as we bounced over rapids and did some fast 360 degree turns.

The scenery is rugged and spectacular and it’s highly possible you’ll see lots of wildlife along the way. Commentary along the six hour tour is informative and entertaining.

There are long (104 miles) and short (80 miles) tours. I recommend the 104-mile Wilderness Whitewater tour with Jerry’s Rogue Jets so you can experience the thrill of the rapids which is mostly featured on the longer tour.

It travels into the ‘Wild’ section, an area only accessible by jet boating, rafting and hiking trail.

You will stop along the way for lunch and a brew if you feel up to it. OR, you can take your own picnic lunch like we did. The picnic spots above the river are serene.

Bears are commonly spotted and the odd mountain lion. We didn’t get lucky with those animals, but we saw plenty of deer and birds.

Stop 18: Tillamook Creamery

The Tillamook Creamery is a cheese factory in Tillamook where you can see behind the scenes of cheese making, including the dairy farm where the cows are kept.

You can watch the cheese being made and of course try their tasty products. Make sure to try some ice cream! This is the freshest place to try it. You can even watch the ice cream being made with their Ice Cream Experience.

Tillamook is also the starting point of the Three Capes Scenic loop on the Northern Oregon coast. It goes south towards Pacific City, and passes three capes; Cape Meares, Cape Lookout, and Cape Kiwanda. The drive is only 50 miles, but it packs a lot in!

Stop 19: Fort Stevens State Park

Fort Stevens is a huge 3,763-acre park known for its wild beaches, hiking and biking trails, and historic fortress. The park is so big, you simply need to make it a stop to enjoy for a day or at least half a day.

The park is most famous for the rusty steel shipwreck, which ran ashore in 1906. But it’s more than this, it has such a varied landscape, from dunes, to lakes, to forest and stunning beaches. It’s definitely worth making a stop here on your Oregon vacation.

Make sure to hike the Cathedral Tree Trail and see the Astoria Column.

Stop 20: Goonies Trail, Astoria and Cannon Beach

Talking about Astoria, don’t miss the home of the ultimate adventure – The Goonies.

Goonies lovers, you cannot visit Oregon without experiencing some of that Goonies magic on your Oregon coast drive. If you are not a Goonies lover, what is wrong with you? Go and watch that movie right now for the passion and big innocent dreaming that comes with youth.

I’ll never forget the moment when we came upon the Goonies vista – you know the one with the rocks jutting out of the rolling surf.

I flashed back to my childhood seeing that in the movie, and one day hoping that I could live a life that had such adventure, connection, and serve a greater purpose. And here I was, doing just that in front in the Goonies world. Be a dreamer!

You’ll find this world at Astoria and Cannon Beach, which is on the northern Oregon coast where the Columbia River meets the Pacific Ocean.

Cannon Beach is one of the best places on Oregon Coast. It’s a charming seaside town with small boutique shops and breweries to explore. And the Goonies magic comes with Haystack Rock on Cannon Beach.

The more dramatic Goonies viewpoint overlooking those sea stack rocks can be found at Ecola Point. A good adventure is to walk from there down to the quiet and stunning sandy beach, Crescent Beach and then onto Cannon Beach.

Astoria then is the town of Goondocks, where the family lived. It is very much like that sleepy fishing village. You can no longer get close to the Goonies house, but you can see it from a few blocks back perched up on the hill.

The Astoria Brewing Company has some cool Goonies merchandise in their special Goonies store.

See more highlights and things to do on an Oregon Coast road trip.

Video: Watch us explore Astoria and Cannon Beach

Scenic viewpoints on the Oregon Coast

Of course, as you’re driving up the Oregon Coast, you’ll take plenty of stops along the way, but if you want to stop off for some views along the coastline, here are some places we recommend you take a break to admire the stunning vistas.

• Depoe Bay
• Ecola State Park (a great place for sunset)
• Indian Beach
• Heceta Head Lighthouse
• Yaquina Bay Lighthouse
• Three Cape lookout (part of the Three Capes Scenic Route)
• Cape Meares Lighthouse
• Cape Perpetua Scenic Area (Where you’ll find Thor’s Well)
• Shore Acres State Park
• Beverley Beach State Park (for whale watching!)
• Sea Lion Caves (the best place to see sea lions)
• Cape Sebastian State Scenic Corridor

Look out for breweries on your Oregon Road Trip

Loosen your belts. We can’t talk about road tripping through Oregon and not mention breweries. It’s one of the best states in the country to sample local craft beer and cider. It’s a bit like Ireland, except it’s a brewery on every corner rather than a pub.

There are around 318 craft breweries in Oregon, many of them operating in a sustainable way and keeping up the state’s reputation for being one of the greenest states in the country.

Don’t drink beer? Unfortunately, neither do I thanks to a gluten intolerance. Not to fear, Oregon has plenty of cider options for you and a couple of gluten free beers can be found here and there.

I was overly impressed with the cider world in Oregon. Usually my choices are limited and not-appreciated, and now I have left, I am quite sad to be left drinking mostly just chardonnay due to pretty awful cider choices.

I felt like I had a different cider flavor in Oregon to enjoy every day. From rhubarb, to marionberry, loganberry to cucumber and gin, this place offers innovative ciders. You will also find innovative brew flavors using local ingredients.

Many of the regions and towns will have brewery trails, helping you to win prizes by collecting as many local brew stickers as you can. I told you to loosen those belts!

• The Bend Ale Trail includes 23 high-desert breweries
• North Coast Craft Beer Trail includes 12 breweries between Astoria and Pacific City.
• Mt Hood Territory Tap Trail takes in 16 ciderie’s and beer crafter’s.

Wine lovers will also enjoy Willamette Valley. We didn’t get to experience much here. Just a couple of nights in Harvest Hosts. I’d like to return and do some more wine tasting. Some of our favorite breweries:

Why take an Oregon Road Trip?

If you’re still on the fence about choosing Oregon as your destination of choice for a road trip, allow me to take a moment to sway your decision. Oregon is wild and free, and a road trip here allows you to show up as you are – when you visit Oregon, anything and anyone is accepted and welcome.

This is a state that at times reminded me of Australia with its coastal beauty and its raw, unfiltered, laid back lifestyle. At other times it reminded me of North Carolina with its mountains, rivers, and pine tree forests and craft brews. Two places I love to call my home.

I spent the entire time of our road trip in Oregon longing to return to both of them. Thankfully, Oregon helped to satisfy that craving a little.

It’s also the best way to see nature spots, since you don’t have to rush off to catch a bus, you can stay as long as you like and never have to worry.

It’s perfect for anxious travelers who like to have everything planned to the letter, as with a road trip in Oregon, you can plan for last minute, make changes to your Oregon itinerary, or just start driving and see where you end up!

Car rentals for Oregon

The first thing you will need for your Oregon road trip is a vehicle (of course). If you don’t have your own, you can find the best deals using DiscoverCars.com, which compares all the major brands like Hertz, Avis, Alamo, and Europcar.

Or, if you want to step your road trip up a notch, you can rent an RV and camp. RVShare is a great platform for finding RVs and motorhomes for rent.

Final thoughts

This is just a sampling of the incredible adventures waiting for you on an Oregon road trip. We were disappointed we did not get to explore more of the hot springs in Eastern Oregon and, especially, the Painted Hills.

We hope you can also experience some of these places on your road trip. If you need more ideas, check out our free PDF of our Oregon Bucketlist. This resource has tons of information to help you plan your trip to Oregon.

Want a free printable PDF of our Oregon Bucket List? It’s available to our email community.

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