View of Mount Hood from the road in Oregon

Two Week Oregon Road Trip Itinerary

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Here is our ultimate two week road trip itinerary for Oregon in the Pacific Northwest of the United States. Our itinerary takes in the best Oregon has to offer from beaches to mountains with plenty of craft beer stops on route.

The best known city in Oregon is Portland. Known for being a bit off-beat with its slogan “Keep Portland Weird” and it is weird – but in the best way. Although Portland is Oregons largest city it is not the capital. The capital of Oregon is Salem – not the one famous for witch trials.

Spending two weeks road tripping in Oregon is a good amount of time to see the highlights this State has to offer. Oregon has a variety of attractions however it is a State that is best suited to those who love spending a good deal of time outdoors. If that’s you then you’re in for a treat.

The largest airport in Oregon is – PDX in Portland. So we will start our two week Oregon road trip itinerary there.

Day 1 – Portland

Street art saying Keep Portland Weird

Portland has excellent public transport and Uber is available throughout the city. You will not need your car while in Portland – with the amount of bars here a car can be a disadvantage!

Hotel Recommendations

There are two hotels we recommend in Portland, both are McMenamins properties. Choose whether you want a city centre location or to stay in one of the cities popular suburbs. Neither is a disadvantage as you will be exploring the suburbs as well as the city centre.

McMenamins Crystal Hotel

The Crystal Hotel is located in downtown Portland, right in the middle of all the action. You will be in walking distance from many of Portlands must see attractions. It is also ideal if you plan on seeing a band play at the Crystal Ballroom nearby – also a McMenamins property.

Private room with ensuite at McMenamins Crystal Hotel Portland

McMenamins Kennedy School

Stay somewhere really unique. Possibly our favourite hotel in Oregon is the Kennedy School. McMenamins have converted this old school into a quirky hotel complete with several bars, restaurant, cinema and pool. Of our two recommendations this one is the more family friendly of the two if you’re travelling with children. If you’re travelling as a couple you can’t go wrong with either the Kennedy School or the Crystal Hotel.

Portland Downtown

Spend your first day in Portland exploring the downtown area. It’s compact and walkable so you can see a lot even in just half a day after you have checked into your hotel.

If you’re visiting over a weekend call in at Portland’s Saturday Market by the Willamette River, you can find lots of handmade crafts here as well as some pretty good street food. You will also find plenty of food trucks throughout the city – a perfect place to grab some lunch.

Don’t miss Powell’s City of Books, the largest independent book store in the world. You could spend hours in Powell’s so you might want to agree a time limit before you go in or you might spend all of your first day there!

Entrance to Powell's City of Books in Portland

In the evening head to one or two of the bars in downtown Portland. Whiskey fans should not miss spending an hour at the Multnomah Whiskey Library where they have around 1000 whiskeys plus 600 or so other spirits. You will be looked after by your own bartender who will help you navigate the extensive menu.

Wall of whiskey in the Multnomah Whiskey Library

Day 2 – Portland

Portland is more than just the city centre. One of the things Portland is famous for is growing roses and on the outskirts of the city you will find the International Rose Test Garden. You can spend some time on a nice day exploring the landscaped gardens which will give you a very different experience of the city to the downtown area.

Something we loved about Portland was the variety of food on offer, from food trucks to independent cafes and restaurants. Our top spots to visit while you’re in the city are the Grilled Cheese Grill, Slappy Cakes, Salt & Straw and Voodoo Doughnuts. I have a bit of a sweet tooth, Salt & Straw and Voodoo Doughnuts are more dessert/treat venues. Grilled Cheese Grill is great for lunch and we had a fantastic breakfast at Slappy Cakes.

Portland is a great city for strolling and people watching and you will want to walk to burn off some of the food you’ve been tempted by! A walk along the Willamette River is great when the weather cooperates, and there’s also plenty of parks. Near Slappy Cakes in the Sunnyside Neighbourhood is Laurelhurst Park which is a small park but full of huge trees which make it seem bigger and as if you’re out of the city.

Willamette River Portland

Day 3 – Astoria – 98 Miles to Drive

Pick up your car today from one of the garages in downtown Portland. Most of the big brands for rental cars have garages downtown so you should shop around to make sure you get the best price. We like to use SkyScanner as a starting point. They have a car rental comparison function as well as flights, just click onto the car hire tab.

Sign on bridge over the Columbia River saying Entering Oregon

Head north out of Portland and follow the Columbia River all the way to the Pacific Coast where the Columbia River joins the Pacific Ocean near Astoria.

Astoria is the home of the Goonies, if you’re an 80s kid you might see some sights you recognise from the film. It was also the location for the film Free Willy for the 90s kids who remember the film climax of Willy jumping over Jessy on the sea wall.

Day 4 – Lincoln City – 109 Miles to Drive

Astoria is located at the northern most point of the Oregon Coast, from here head south for the next few days driving the entire Oregon Coastline to the California border.

Driving south on highway hwy 101 in Oregon State, USA

Expect to spend approximately 3 hours behind the wheel today. With an early start this will give you plenty of time for stops along Oregons northern coast. There are plenty of beaches to explore on this coast, when you do stop keep an eye out for whales which can been seen occasionally from shore. We were lucky enough to see a humpback while road tripping the Oregon coast!

If you’re a foodie don’t miss stopping at Tillamook on this leg of the road trip. You can take a tour at the Tillamook Creamery – you also get some free samples!

Stay overnight in Lincoln City. It’s a large coastal town. Plenty of places to get good quality seafood and take in some more ocean views and relax before hitting the road again in the morning.

Day 5 – Florence – 74 Miles to Drive

Keep heading south on Highway 101 and you will be treated to even more spectacular views. We recommend taking Highway 101 south rather than reversing this itinerary. When heading south you have unobstructed views of the Pacific from the road since you’re driving in the lane closest to the ocean. It makes it so much easier to stop at all the view points along this route.

Between Lincoln City and Florence there are some great stops. You will only need to spend 2 hours behind the wheel today so there is plenty of time for exploring.

The Oregon Coast Aquarium is on route which is the aquarium that housed Keiko the Orca from the Free Willy film. We don’t agree with keeping Orcas in captivity, this was two decades ago, but it gives you an idea of the size of this aquarium.

heceta head lighthouse, Oregon Coast, USA

Further south you will be greeted to the sight of Heceta Head Lighthouse which is said to be the most photographed lighthouse. Near Heceta Head Lighthouse is another stop – the Sea Lion Caves. You can ask before paying to enter the caves whether the Sea Lions are in or not, their activities depend on the season. When we called by in September they were out at sea feeding so the cave was empty. You can still get some great views from here though so it’s worth a stop anyway.

Entrance to the Sea Lion Caves in Oregon

Stay in Florence for the night. It’s a small town just 11 miles further south from the Sea Lion Caves. If you get to Florence early it’s a cute small town you can spend a few hours relaxing in. There are a few restaurants, a decent cafe and a small board walk onto the river.

Day 6 – Bandon – 73 Miles to Drive

There is good reason to stay in Florence for the night as it puts you in the perfect location to hit the nearby sand dunes first thing in the morning. We recommend booking a sandrail tour with Sandland Adventures. You will see so much more of the sand dunes than you would if you hired your own smaller vehicle. The drivers of the sandrails are experts and they can pick up a lot of speed!

It’s only a short drive with even more gorgeous Pacific Coast views to the town of Bandon. Although there are a few small towns between Florence and Bandon we recommend spending most of the afternoon as well as the evening in Bandon, it was one of the highlights for us on this stretch of Highway 101.

If you’re wanting to shop for some souvenirs then you will find plenty of options in Bandon. There are also plenty of places to eat, have a drink and relax by the water.

Day 7 – Cave Junction – 150 Miles to Drive

To get from Bandon to Cave Junction the route takes you into northern California for a few miles. You have the option of calling in at Crescent City for a pit stop where you may get to see some California sea lions.

Take in your last views of the Oregon Pacific Coast before leaving Highway 101 to head in land.

Southern Oregon Coast

Cave Junction, if the name doesn’t give it away, is home to the Oregon Caves. You can stay over night here at the Oregon Caves Chateau and take a tour of the caves which takes around 90 minutes. In the summer you can expect a long wait to take the tour of the caves which are a popular attraction in southern Oregon.

Day 8 – Crater Lake National Park – 140 Miles to Drive

Crater Lake National Park is a popular attraction in Oregon and so a must visit on our two week Oregon road trip. The crater was formed by the collapse of volcano Mount Mazama thousands of years ago. From the Oregon Caves expect the drive to take around 3 and a half hours.

Crater Lake National Park is generally covered in snow until late spring to summer. Spring arrives later than the rest of the State due to Crater Lakes high elevation. If you’re visiting outside of the summer season be prepared for cool or even cold weather and that some of the roads may have closures. Although there are still activities here when the snow is still on the ground – try your hand at snow shoeing around the lake!

Days 9 – 11 Bend – 102 Miles to Drive

Bend is possibly our favourite city in Oregon. It has a similar vibe to Portland but it’s smaller and more compact. It also has its very own ale trail you can take part in – and if you complete it you get a prize!

Bend Ale Trail in Oregon

From Crater Lake National Park to Bend you have a fairly straight forward drive of around 2 hours. We recommend spending 3 nights in Bend and our favourite hotel is another McMenamins property – Old St. Francis School. Old St. Francis School is similar to Kennedy School in Portland in that it is a converted school. It contains a few different bars, a heated soaking pool and a cinema.

Mcmenamins Old St Francis School in Bend

You will want a day or so just to get around a few of the bars and excellent food spots around Bend. We can recommend the food at Old St Francis but also we loved McKay Cottage Restaurant and Bangers & Brews. For a fun experience check out Dandy’s Drive-In too, a genuine 1960s drive in which was established in the 60s and is still going strong today.

By taking part in the Bend Ale Trail you will get to see a lot of Bend including suburbs you wouldn’t head out to otherwise and we found some of the best bars, breweries and eating spots were out in these areas. 10 Barrel Brewing had a great local vibe and was very busy on a midweek afternoon. If you’re not a beer drinker then don’t miss out on visiting Avid Cider where they have a great range of ciders – you can even get a tasting flight.

Get outside of the city

Spend at least one day outside of Bend. It is an outdoor adventurists paradise. You can take a kayaking trip on the nearby Deschutes River. Head to Mt Bachelor to hike or even ski if you’re there during the ski season. Take a self guided tour of Lava River Cave near Newberry National Volcanic Monument. The options are endless, you will want to make plans for a return visit to Bend after your two week Oregon road trip I’m sure.

Bend, Oregon

Day 12 – Hood River – 145 Miles to Drive

Hopefully you found some time to relax in Bend, you will want an early start to head to Hood River which should take around 3 hours. You will drive through more forest landscapes today but also you will see some landscapes you would associate more with the likes of Arizona.

Varied landscapes of Oregon

The forests return as you drive closer to Mount Hood. Mount Hood dominates the skyline as you get further north so you won’t miss it. As you make your way up to Hood River you will drive around the eastern slopes of the mountain. If you want to explore this area more it would make a great pit stop on route to Hood River.

Mount Hood, Oregon

Hood River is a large town on the banks of the Columbia River in northern Oregon. It has a variety of craft breweries and great places to grab a bite to eat. If you want to try something other than craft beer it’s here you will get your chance as many tour companies run wine tours from Hood River. This area including the towns on the opposite side of the Columbia River have quite a range of vineyards for you to explore – and taste the produce from.

Day 13 – Troutdale – 70 Miles to Drive

Don’t rush back to Portland, one of the highlights of your two week Oregon Road Trip is left for last – the Columbia River Gorge and its famous waterfalls.

First stop on the way back towards Portland should be Cascade Locks. Here you can get a view of the Bridge of the Gods and stop for a snack or lunch by the river. It’s beautiful sitting out by the river on a nice day.

Great pit stop at Cascade Locks Oregon

Get back onto the highway heading towards Portland but take the exit at Dodson onto the Historic Columbia River Highway. Take this scenic route all the way to Troutdale which is on the outskirts of Portland.

Plan to spend at least a few hours on this drive as you will want to stop a lot to do some of the short hikes to the waterfalls, maybe even one of the longer ones. Even if you don’t like hiking take this road as there are a few of the waterfalls that can be seen right from the road.

Amazing waterfalls of the Columbia River Gorge

You will find a rest stop at Vista House where you will also be greeted to amazing panoramic views of the Columbia River Gorge. We found plenty of parking during our visit in June. If you are travelling during peak summer you may find it a bit more difficult to park. It is worth a short wait though if you find yourself in a queue for parking.

When you complete your drive of the Historic Columbia River Highway consider staying outside of Portland, possibly in Troutdale. Keep your car for your last night as it will come in handy for getting to the airport to fly home the following day. Hotels outside of Portland city centre generally have free parking.

One hotel which is on our list to stay at is the McMenamins Edgefield Hotel in Troutdale. This hotel was an old farmhouse and still has a 74-acre parcel of farmland at the mouth of the spectacular Columbia River Gorge Scenic Area. Along with the bars and restaurants you come to expect when staying at a McMenamins hotel the Edgefield goes a step further and has a spa as well as a golf course. You’re sure to find something to do here for your final night of your two week Oregon road trip.

Day 14 – Return home

Staying in Troutdale puts you just 15 minutes drive from Portland PDX airport. Remember to set off in plenty of time to return your car. The rental car drop off at PDX is off site but is very smoothly operated. Simply drop off your car and jump on the shuttle bus which leaves from the drop off point to the airport. The journey takes less than 10 minutes.

We hope you find our two week Oregon road trip itinerary useful. If you have more than two weeks then head north to see a bit of Washington State, another outdoor enthusiasts paradise! Or you could head south and visit the redwoods in northern California – you can’t go wrong with either option.

Let us know your favourite places to visit in Oregon in the comments.

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