Oregon Road Trip: How to Make the Most of Oregon in 10 Days

Last updated on March 26, 2024

Suttle Lake at Suttle Lodge

I’ve always romanticised the Pacific North West – the misty coast, snow-capped mountains and rugged, outdoorsy lifestyle with a distinct hipster bent. And you know what, Oregon lives up to my dreams. There’s many a bearded person dressed in plaid and hiking boots, the coffee is elite, and it’s all set to a stunning mountainous backdrop. It’s a state that makes for an epic US road trip.

We spent 10 days exploring some of our bucket list Oregon destinations, taking in parts of the coast, the inland mountains and, of course, Portland (just look at us – people constantly tell us we should live there!).

Here are all the details of our 10-day Oregon road trip, including where we stayed, what we ate, the routes we took, and everything you need to replicate it. We’ve also included some extra stops that we didn’t manage to do, but that you might like to add. 

Enjoy! And, as always, just let me know if you have any questions.

How to use this Oregon road trip guide

There are a few options when it comes to using this Oregon road trip planner. Most simply, you could copy the whole thing in its entirety (and we can vouch for that as an excellent option!). Or choose the destinations that resonate with you and create a route based on that. Or perhaps do a mixture of the two – it’s adaptable to your priorities.

For example, our priorities were: epic scenery that’s accessible with kids, excellent food, creative towns and special places to stay. If yours are different, you might make some of our overnight stops into day trips (for example Sisters) or vice versa (like making Columbia River Gorge an overnight stay). And we’ve also included some suggested destinations that we didn’t have time to include, but that might be a priority for you.

We’ve also added some general Oregon road trip tips and FAQs, followed by guides to each destination, including things to do, places to stay and where to eat. We delve into each destination in more detail in other posts around the site (especially Portland, which we’ve been to several times).

For more travel inspiration, see all our road trip itineraries and our in-depth guide to how to plan a road trip.

Who is this route for? Families, couples?

High Desert Museum, Bend.

We did this Oregon road trip as a family of four with a 1 and 4-year-old, but as with most Bridges and Balloons itineraries, it would also suit couples or solo travellers – you just might want to skip some of the more kid-centric activities. We try not to sacrifice our own tastes and style, even when travelling as a family, so the places we stay and the things we experience are similar to what we’d have done pre-kids. For example Suttle Lodge is exactly our sort of pre-kids style.

If you’re not travelling with kids and you’re very active then Oregon has loads of adventure sports you can add to this itinerary. You could follow the same route, but do more outdoor sports than we did. I’ve included some options with each destination. And there are also extra stops like the Willamette Forest, Umpqua National Forest and Mount Hood that would be particularly good for adventure lovers. 

I would have particularly loved to visit some of the remote hot springs and done some of the more tricky waterfall hikes had we not been with the kids.

Oregon road trip at a glance

  • Astoria and/or Cannon Beach – 2 nights
  • Portland – 2 nights
  • Sisters – 1 night
  • Bend – 2 nights
  • Crater Lake – 1 night
  • Ashland – 1 night 

Optional extras

  • Painted Hills
  • Mount Hood
  • Columbia River Gorge
  • Willamette Valley
  • More Oregon Coast (Florence, Seaside, Lincoln City)

Our Oregon road trip highlights

  • We’re huge fans of Portland – it’s a place we could easily live – so a visit there is always a highlight, especially for the food.
  • Cannon Beach is as spectacular as it looks
  • Suttle Lodge is a gorgeous special stay – a hip, lakeside camp by the creators of the Ace Hotel
  • For out-of-this-world beauty, head to Crater Lake
  • Sisters is the place to go for small-town charm with a western cowboy edge

Oregon road trip map

Oregon road trip FAQs

How long do you need for an Oregon road trip?

The route we’ve outlined can be comfortably done in 10 days, but personally we’d add an extra night or two in the places that appeal to you most. You could also cut out some destinations to achieve a slower pace of travel. And bear in mind where you need to get to – for example which airport – at the end of the trip to make your way home.

When to go to Oregon

As with most things, when to go to Oregon depends on your priorities. The quietest and cheapest time to visit is November to January, but this is also the time of year when it’s cold and rain is almost certain. Some trails will also be closed at this time.

For snowsports, February to April is the time to go. But bear in mind that snow may cause road closures, which might stop you from visiting some of the more remote areas. We had to change our plans even in May because of snow!

And September/October is great for wine lovers as it’s harvest time in the Willamette Valley. 

For hikers and lovers of outdoor sports, June to September are the warmest months with the most sunny days. And this is also the best time of year to enjoy the coast. While busy, the beaches are huge, so it doesn’t feel too crowded (hotels may book up though). 

We’ve been to Oregon in the Spring and Fall. Both were beautiful, but we think Fall has the edge as the colours are gorgeous and we love the festive vibes around Thanksgiving and Halloween. The days were also surprisingly warm and sunny in early October.

What to pack for an Oregon road trip

What you pack will depend on the level of adventure you’re aiming for, and of course the time of year. But here are some essentials.

  • Hiking boots/shoes – Oregon is the land of hiking and you’re bound to try at least one while you’re there. Plus you’ll fit in nicely with the locals! Danners are a local and very popular hiking boot brand.
  • Sunscreen – no matter the time of year sunscreen is always a good idea. Protect that skin – it’s the only one you’ve got!
  • Water bottle – essential for any road trip and outdoor adventure. We all have Klean Kanteen bottles.
  • Snacks – good snacks are the secret to both an excellent road trip and a hike. Make up a good trail mix, especially one the kids will like. You could add in some treats like smarties to keep them invested!
  • Camera – I either use my iPhone or now I have the Fuji X100VI
  • Day pack – Oregon is one of those places where having a day pack will definitely come in useful when exploring the beaches, hikes etc. I love the Fjallraven backpacks, but Osprey is probably better for hiking backpacks.
  • Rain jacket – Oregon is known for its rain, so make sure you’re prepared!
  • Layers – layers are good for any time of year, but pay special attention in the colder months when thermals will come in handy.

How to get around Oregon

We hired a car with Discover Cars, our favourite site for rentals. They search hundreds of other rental companies and tend to come back with the best deals. They also have good cancellation/amendment policies. I also recommend checking Expedia as between the two, you’ll find a good deal.

Bear in mind it’s often cheaper to rent for a week-long period rather than an odd number of days (you often get a discount for seven days or a month), so play around with the booking dates and see what comes up. Find the latest deals here.

Oregon would also be an ideal place to rent a campervan. There are plenty of campsites and it’d be a great to immerse yourself in the state’s nature.

Where to start and end your Oregon road trip

For the purpose of this Oregon-focussed itinerary, I’ve started and ended with stops in Cannon Beach and Ashland. In reality, we did a longer trip, starting in Seattle and continuing down to San Francisco.

If you’re coming from afar, you’ll likely fly into Portland and drive to Cannon Beach from there. Ashland has its own small airport, plus it’s close to the international Medford Airport, so you could return your car to one of those.

Read this post
19 unmissable things to do in Sonoma County, California

Or you could extend the trip back to Portland, driving up the coast rather than inland (I’ve included details of that option in the itinerary). 

Bear in mind, if you’re starting and ending your road trip in different destinations and need to return a hire car somewhere else, you’ll have to pay an extra fee.

How to get to Oregon

There are two international airports in Oregon: Portland (PDX) and Rogue Valley International Medford Airport (MFR). Plus there are lots of smaller regional airports too. We recommend searching on Skyscanner for the best deals and setting up a flight price tracker so you can jump on price reductions. 

Our detailed Oregon road trip itinerary

Cannon Beach and Astoria

Kids playing on Cannon Beach

Have you ever seen The Goonies? If so, Cannon Beach and Astoria will be familiar sights. And even if you’re not up on your 80’s films, Haystack Rock is probably an image you’ve come across. The iconic rock on Cannon Beach rises magnificently from the shallows of the Pacific, and the beach regularly makes lists of the most gorgeous places on earth.

It’s an epic beach with wide, sweeping sands that calls for long, scenic walks by day and campfires by night. 

Its beauty is no secret and crowds flock to Cannon Beach, especially during the summer months. However, it was fairly quiet when we were there in April.

I’ve also included the charming riverfront town of Astoria in this section, but it could easily be its own destination and stop for the night. I actually prefer the vibe in Astoria as it has lots of cool, local businesses. But for iconic scenery, I don’t think you can beat Cannon Beach, so I’d definitely prioritise that. 

Things to do in Cannon Beach and Astoria

Kid playing on Cannon Beach.

The very best thing to do in Cannon Beach is simply enjoy the beauty of it all and do all the things that beaches beckon, from long walks to building sandcastles. 

For something extra, here are some ideas for more things to do in Cannon Beach…

  • See the puffins – in Spring, from around April to July, a colony of puffins take up residence on Haystack Rock to nest and raise their young. At low tide, you can walk right up to the rock and try to spot them
  • Go tidepooling – the beach has lots of good opportunities for tidepooling at low tide, especially around Haystack Rock. The Haystack Rock Awareness group offer guided tours where you can learn more about the beach and its wildlife.
  • Have a campfire on the sand – an iconic image for me of the Pacific North West is people having campfires on the sand. Cannon Beach is a perfect place for this, and some of the hotels offer a campfire service, helping you make one if your skills (or will) aren’t quite up to it.
  • Cannon Beach is part of Ecola State Park, which covers nine miles of coastline between Cannon Beach and the neighbouring town of Seaside. There are lots of hiking trails to explore with stunning views of the coast.
  • Explore the towns and its galleries – Cannon Beach is tiny but manages to pack in 15 art galleries including the cool Icefire Glassworks. There are also art festivals and events throughout the year. Another must on our list is the Cannon Beach Bookstore.
  • Go to Hug Point – this is around 5-10 minutes from Cannon Beach and a beautiful place to go for a walk, play in the waterfall and explore the caves and tide pools.

And in Astoria, these are some popular things to do…

  • Walk along the Astoria Riverwalk and to the end of the Pier 39 to enjoy the views
  • Hike to Cathedral tree, an often muddy but fairly easy short hike
  • Flavel House – if you’re a history buff, visit this restored mansion from the 1800s, which was once owned by the richest man in Astoria
  • Astoria has been the location for many films like the Goonies, Free Willy and Kindergarten Cop. Use the SetJetters app to do a self-guided tour of the filming locations.

Where to eat and drink in Cannon Beach and Astoria

Don’t go to Cannon Beach expecting the level of creative culinary excellence that you’ll find in Portland. This is not a foodie town. But there’s a few good options to try.

  • Pelican Brewing – this brewpub is one of the most popular spots in town, serving beers and comfort food. Its popularity means you might have to queue (we waited around 15 mins in low season)
  • Public Coast Brewing Co – another popular brewpub that serves locally grown food
  • Suzy’s Scoops – the place to go for ice cream in Cannon Beach
  • Sea Level Bakery – home to the best coffee and baked goods in town

In Astoria, we recommend

Where to stay in Cannon Beach or Astoria

SurfSand Resort is one of the most memorable stays we’ve ever had, largely due to the views, followed by the kiddie bath robes and cookie hour! The hotel is right on the beach, and we had a fabulous ringside view of Haystack Rock straight from our balcony.

The daily ‘cookie hour’ sees fresh bakes and milk in the lobby. And they even provide kiddie-sized robes in the rooms (a huge hit with Otis and Arlo!).

Other highlights include a heated indoor pool, fitness center, and cosy guestrooms, complete with a fireplace to snuggle up by. The onsite restaurant, Wayfarer, is great for families with a relaxed beachy vibe. And best of all, they offer a nightly campfire and s’mores service where staff help you build a fire on the sand.

It’s not a remarkably stylish hotel, going for a more classic, American look rather than anything creative, but the rooms are cosy, and the bathtubs, fireplaces and views elevate the whole experience.

It’s certainly a special stay. Find the latest prices and deals here.

Other hotel options in Cannon Beach include:

We didn’t stay in Astoria, but we were recommended the Bowline boutique hotel by friends.


I love Portland. I’d move there in heartbeat (if only I could convince all my friends and family to do the same!). It’s a small city that packs a lot in, not least one of the most exciting culinary scenes in the USA.

But it’s not just about the food – it’s also the creativity that carries through to all parts of travel, from the cool hotels to the cute cafes and indy boutiques. It’s part of the fabric of what makes Portland cool (or weird as it’s known). If you’ve seen Portlandia, you’ll know the stereotype and it’s really not far off. We bloody love it, and it makes for an amazing city break.

Things to do in Portland

For proper in-depth guides, see our post on what to do in Portland, plus another on things to do in Portland with kids.

Some of the highlights include:

  • Powell’s City of Books – the world’s biggest independent bookstore, occupying a whole city block. The rare books section is Steve’s personal heaven.
  • Mount Tabor Park – from Mount Tabor Park (built on an extinct volcano), you have a great view across the city and of Mount Hood in the distance. There’s also a good woodland playground.
  • Portland Japanese Garden – considered one of the most authentic Japanese gardens outside of Japan and lovely for a scenic walk in the shade.
  • Columbia River Gorge – a designated National Scenic Area just 40 minutes from downtown Portland with lots of excellent hiking opportunities
  • Explore all the local neighbourhoods. Our favourite is the Alberta Arts District, filled with cool shops, cafes and restaurants.
  • Go to a vintage video game arcade – a couple we recommend are Ground Kontrol in downtown Portland and Quarter World Arcade on SE Hawthorne.

Where to eat and drink in Portland

The biggest question of all – where should you eat in Portland? The pressure is on as food is such a big part of this city and it’d be a sin to eat badly. I’ve made a guide to veggie-friendly restaurants in Portland (all suitable for meat eaters too). And these are some of our favourites:

Where to stay in Portland

I’ve written a guide to the best Portland Airbnbs. But there are also many excellent hotels. And it’d be a great place to do a home exchange as then you could get under the skin of true Portland life.

These are a few of our favourite hotels…

Hotel Zags

We stayed in Hotel Zags on our most recent Portland trip. It’s perfectly located in the Fountain District and has a cool style with lots of art and a big garden patio area.

Highlights include the Gear Shed where you can hire all sorts of things from bikes to guitars to video game consoles and skateboards! And they also have fire pits in the garden and a little shop where you can buy s’mores kits to roast at night. 

It’s in downtown Portland, which isn’t one of the cool, local neighbourhoods that we love the city for, but it is in a really convenient location for sightseeing.

Read this post
21 Unmissable Things to Do in Savannah with Kids

Book your stay now.

Hip hotels in Portland

There are lots of trendy hotel options in the downtown area, which would be a convenient place to stay for a short trip to the city. Some of the best options are: the uber-trendy Ace Hotel; the Hoxton Hotel (my go-to hotel brand); and the Hi-Lo, part of the design-conscious Autograph Collection.

How to get around Portland 

Unusually for America, Portland has an excellent public transport system, the Trimet, which includes a max light rail, buses and streetcars. The Trimet travel planner is a handy way to plan your route, and you can use the app to buy digital tickets without the need for cash. A $2.50 ticket allows you to use any form of transportation within two hours, and there are also daily and weekly passes available.

Another good way to get around is by bike as the city makes it easy with loads of bikeways and the USA’s highest percentage of bike commuters. It even has the title Bike City, USA (just don’t tell Davis, California that!).

If you’re reading this post, you’re likely on a road trip and will have a car. The city is easy to drive around (just avoid rush hour) and parking is fairly cheap (SmartPark garages start at around $1.50 an hour). 

Sisters and Suttle Lodge

Sisters Oregon.

As you may know by now, I’m a sucker for a cute town, and Sisters is a perfect example. It’s a place where you feel like you’ve stepped back in time to the 1880s. Wooden sidewalks line the street and many of its buildings have been decorated to look like they’re from a Wild West town. It has a thriving local community, outdoorsy vibe with a buzz around the local café and notice boards filled with events. 

You could easily visit Sisters as a simple day trip from Bend (it’s only 30 minutes away). But we think it’s a destination in its own right, largely because of the fabulously hipster Suttle Lodge – one of the most special places to stay in Oregon. Think log cabins in the woods, a lakeside hangout, and beards a plenty, drinking craft brews and fine foods.

Things to do in Sisters and Suttle Lodge

  • In Sisters, explore the cute downtown with all its boutiques, galleries and restaurants. The public restrooms are marked for cowboys and cowgirls! And the post office is named the Pony Express. We loved the local Paulina Springs Bookstore too.
  • At Suttle Lodge, relaxation is name of the game, and it’s the ideal place to switch off phone and enjoy the great outdoors.
  • Suttle Lake is spectacular and a good way to appreciate it is to walk the Suttle Lake Loop, a scenic, 3.6 mile (5.7 km) loop trail around the lake’s perimeter. The trail is fairly flat and stays very close to the shore for the most part.

Where to eat and drink in Sisters and Suttle Lodge

Suttle Lodge has its own excellent restaurants and bars. The Boathouse by the water is open seasonally for riverside dining (closed when we visited). And Skip is the lodge’s cocktail lounge, open year-round. Skip serves breakfast, lunch and dinner, as well as a top-notch cocktail menu. I can confirm their old-fashioned is perfection.

In Sisters, we recommend trying these places:

  • Sno Cap Drive-In – an old-time drive-in that’s been serving homemade ice cream since 1952. It makes for a perfect Americana-style experience (and photo!)
  • Three Creeks Brewery – a kid-friendly brewery and pub in a lodge-like woodland setting, serving pizza, burgers and pub grub
  • Sisters Bakery – for indulgent baked goods aplenty
  • Sisters Coffee Company – excellent coffee and amazing scones!

Where to stay in Sisters

As we’ve said, the main reason we suggest Sisters as an overnight stop is to experience the gorgeous Suttle Lodge. From the people behind famously cool Ace Hotels, it’s a fabulously hip take on a rustic, lakeside resort.

The setting itself is spectacular in the Deschutes National Forest and on the edge of Suttle Lake, which sparkled ice blue when we stayed.

The whole place is perfect for whiling away the days hiking, boating or simply relaxing in nature. It comes into itself in summertime, but even colder days, like when we stayed, are gorgeous.

The cabins are perfectly put together, ranging from rustic options to more luxury affairs with fireplaces and a jacuzzi tub. And there are fire pits and adirondak chairs for relaxing come nightfall.

We fell in love with the place, and highly recommend you make it a stop on your Oregon road trip.

Book your stay now.


Bend Theatre.

Bend is a mecca for lovers of the outdoors, filled with opportunities for adventure (and drinking beer). Take your pick from skiing to mountain biking to rock climbing or kayaking. And then, when the day’s over, head to one of the brewpubs to explore the town’s famous craft beer scene.

Lumberjackets and beards abound in Bend (so Steve slotted in perfectly!) and its setting is gorgeous, surrounded by snow-capped mountains, forest and the high desert landscape. We also loved exploring its cute downtown area with lots of indy boutiques, cafes and restaurants.

We’ve suggested spending two nights there in this itinerary, but you could easily stay for longer.

Things to do in Bend

Top of your agenda in Bend should be exploring some of the town’s outdoor activities. Here are some ideas for tours you could join, including snowshoeing and canoeing by moonlight.

Powered by GetYourGuide

And here are some more top things to do in Bend…

  • Go hiking – popular trails include Green Lakes Trail and Broken Top. Or for a more low-key option, go for a leisurely stroll along the Deschutes River. There are trails on both sides of the river and three footbridges connect the trails. They’re great for kids on bikes or scooters. Our littluns love this.
  • Explore the town’s breweries (see some recommendations below). Or do the Bend Ale Trail.
  • Wander the downtown area, being sure to pop into Dudley’s Bookstore. The Bend Store is the place to go for stylish souvenirs.
  • Go floating on the Deschutes River – the most popular summer activity in Bend is grabbing a tube or SUP and floating down the river. See this guide for lots of tips!
  • Go to the last Blockbuster rental store in the world!
  • Visit the High Desert Museum where you can explore and learn about the natural world and cultural history of the High Desert. It’s good for kids with an animal area and trails outside. They also do good exhibitions – they had one on counter culture in the 70s when we were there, which was fascinating.
  • Around 30 minutes from Bend is Smith Rock State Park, the birthplace of sport climbing. As well as lots of opportunities for climbing, it’s also a stunning place and has hikes for all abilities.

Where to eat and drink in Bend

Bend is more of a beer than a foodie town, but there’s still some good meals to be found.

  • We loved the food trucks and beer at On Tap (the Philly cheese steak truck was fun), which is just outside the main downtown
  • For brunch, we loved The Victorian (fantastic huevos rancheros) and we hear McKay Cottage and The Lemon Tree are great too.

For cafes, we recommend:

  • Backporch Coffee Roasters – great coffee in the downtown area
  • The Commons – a lovely cosy café, perfect for long chats, board games and reading a book. If I lived here, this is where you’d find me!

And here are some recommendations for breweries in Bend. We (and the kids) particularly liked Crux where they had a big garden with cornhole and a couple of food trucks. It made for a wonderfully relaxing evening.

Where to stay in Bend

We stayed at The Element in Bend in an incredible studio apartment. The studio is flexible accommodation with up to four-bedrooms and a shared common space. We were lucky and had the whole common space to ourselves.

The hotel is perfectly set up for longer stays and all the rooms have their own kitchen. They also offer complimentary bikes, perfect for exploring Bend. And there’s a pool and spa onsite. It’s just across the road from the Deschutes River and is only a 10-minute walk from downtown Bend.

It isn’t particularly interesting in terms of style, and it leans more towards a corporate look (it’s a Marriott), but there are quirky elements like toy dinosaurs hiding in plants, which the kids loved. I’d go to McMenamins if you’re looking for something unique. 

Rooms start at $130 per night. Find the latest deals here.

Other places that are highly recommend include:

  • McMenamins Old St Francis School – The McMenamins brand is an expert in transforming historic buildings into characterful entertainment hubs. The one in Bend has a hotel, restaurant, bar, cinema and soaking closet. It’s worth a visit even if you aren’t staying there.
  • Campfire Hotel – a hip boutique motel lodge
  • The Loge – a cool outdoor-adventure-focused hotel with gear rental too

How to get around Bend

If you want to leave the car behind, Bend has a public transport system with several bus lines. Use the CET transport planner to plan your route. You can even get to Sisters on public transport.

Bikes are very popular in Bend and there are a few hire shops including Sunnyside Sports.

You can also get all the way to Portland on the Central Oregon Breeze.

Redmond is the nearest airport, and the easiest way to get between there and the centre is with the Enviro Shuttle. You could easily do a trip to Bend without a car at all (although you’re likely on a road trip if you’re reading this!).

Crater Lake 

Crater Lake.

Crater Lake is a bucket list natural wonder in the heart of Oregon. The lake sits in a dormant volcano that erupted around 7,700 years ago! It’s the deepest lake in America and one of the cleanest and clearest in the world, with an incredible depth of blue. It’s obvious why it has the nickname “Lake Majesty”.

While you can visit the lake year-round, it’s important to note that not all the driving routes, facilities and viewing points are open in the colder months. Plus the colder months often have very poor visibility, so you could easily visit the lake without seeing it at all! For example, in May, the lake is invisible 20% of the time. Visibility is at its best in the summer, and that’s also when everything’s open, so the most reliable time to go.

Read this post
11 Gorgeous Airbnbs in Santa Monica

Unfortunately, for our visit, the lake was completely hidden so we bypassed it on our road trip (we knew it was hidden because we checked the conditions here). Luckily, we love Oregon, so no doubt we’ll be back – it’s definitely still on the bucket list.

Because we’d planned to visit and I’d done all the research, I’ve still included recommendations from our plans below.

When visiting Crater Lake on your road trip, you could stay nearby to give yourself time to explore the lake and all it has to do, or you could simply stop there en route from Ashland to Bend.

Things to do in Crater Lake

Close up photo of Crater Lake.

Things to do in Crater Lake vary by the time of year, but the highlight will be simply seeing the magnificent lake. One of the best ways to do this is on the Rim Drive, a 33-mile road circling the entire lake, with lots of viewing areas along the way. The drive closes around 1 November every year and re-opens around mid-May to late June, depending on snowfall. Check the latest conditions here.

In the winter, you can still normally view the lake (if it’s visible!) by driving to Rim Village.

Other things to do in Crater Lake include:

  • Ride a boat to Wizard Island, a cinder cone that rises from the lake
  • Go hiking on over 90 miles of trails
  • Explore Crater Lake National Park’s other natural wonders, including waterfalls and forest
  • In the winter, do a snowshoe walk – hire snowshoes at the Rim Village Gift Shop and ask them for advice on where to go.
  • Tour Crater Lake Lodge – explore the lake’s history and attend a ranger talk at this historic hotel

Where to eat and drink in Crater Lake

There are a few restaurants/cafes in the park itself, including the restaurant at Crater Lake Lodge, the Rim Village Café and Annie Creek in Mazama Village.

Where to stay in Crater Lake

How to get around Crater Lake 

You’ll need a car to visit Crater Lake. The only other way is to join a guided tour. There are a few options below.

Powered by GetYourGuide


Ashland went straight onto my bucket list as soon as I first heard about it. I love towns where creativity reigns and Ashland is definitely one of them, filled with galleries, theatres and restaurants. It’s home to the world-famous Oregon Shakespeare Festival and always pops up on lists of the most charming towns in America.

Sadly, the charming little mountain town is still on our bucket list! We were all set to go but then snow blocked the road and we had to re-route! I’ve left it on this itinerary as it was part of our original plan, and I’m almost certain we (and you) would love it. 

And, like with Crater Lake, we did lots of research, so I’ll share the places we planned to visit while there.

Things to do in Ashland

Here are some ideas for things to do in Ashland:

  • Catch a show at the Oregon Shakespeare Festival, which runs from February to October each year.
  • Hike part of the Pacific Crest Trail (which stretches from Mexico to Canada!)
  • Visit the ScienceWorks museum
  • Visit local wineries (you could follow the Bear Creek Wine Trail)
  • In the winter, ski at Mount Ashland
  • Spend some time in Lithia Park where you can explore its playgrounds and trails.

Where to eat and drink in Ashland

These places come highly recommended in Ashland:

  • Oberon’s – an eclectic restaurant and whiskey bar. Apparently, “Ashland’s most Ashlandiest spot”!
  • Caldera Brewery – cool space with brewery and restaurant. Orgeon’s largest beer bottle and can collection lines the soaring walls.
  • Larks Restaurant – good for farm-to-table dining.
  • Alchemy – upscale dining in a gorgeous wooden house.

Where to stay in Ashland 

We had planned to stay at the Arden Forest Inn, because I think a charming town calls for a charming stay and this B&B looks perfect. 

Other recommended places to stay in Ashland include:

How to get around Ashland 

Ashland is a walkable town so you don’t need a car if you stay centrally in town. You can get a taxi or the Cascade Shuttle Bus from Medford Airport to Ashland.

Other Oregon road trip destinations

Here are some extra destinations you could add to an Oregon road trip…

Columbia River Gorge

We included Columbia River Gorge in the Portland section as it can be done as a day trip from there. But you could also make it its own overnight stop on your road trip, especially if you’re looking for outdoor adventures.

The gorge is over 80 miles long and extends into Washington State. There are more than 90 waterfalls (and that’s just on the Oregon side), so it’s a great place for hiking and scenic spots. The Historic Columbia River Highway is a great road for waterfall spotting, including the famous Multnomah Falls.

Columbia River Gorge also has lot of wineries, so you could top off a day of hiking with some tastings. 

If staying here, the best town is Hood River and the Hood River Hotel.

Mount Hood

One of the most spectacular sights in Oregon is Mount Hood, the state’s tallest mountain. You could pass through en route to Sisters/Bend from Portland, or make it an overnight stop. One of the best views of the mountain is from Lost Lake, but it’s not an easy hike to get there, so not one we wanted to do with the kids. 

You can also go skiing at Mount Hood throughout the whole year (only place in Oregon that this is possible).

This area is also well known for its fruit farms – follow the fruit loop to sample some of the best.

Painted Hills

The painted hills of Oregon do as they say on the tin and look like someone’s taken a paintbrush to the landscape. The colours change in different light and moisture conditions, and they’re considered on of the seven wonders of Oregon. The hills are fairly out of the way, so we’d only add them to your road trip if you’re super keen to see them.

Willamette Valley 

The Willamette Valley includes Portland, as well the cities of Eugene and Salem. 

To the west of the valley is the Willamette National Forest where you can visit more natural wonders, like the Cougar Hot Springs and Tamolitch Falls, which have an unbelievably deep blue pool at the bottom.

Umpqua National Forest

If nature is your number one, you could miss out Ashland and head to the Umpqua National Forest after Crater Lake. There are some gorgeous looking hikes there, including  waterfalls and the natural Umpqua hot springs.

Silver Falls State Park

If you’re near Salem, consider a trip to the nearby Silver Falls State Park where you can explore around 10 gorgeous waterfalls. The Trail of Ten Falls hike takes you past them all on a 7.4 mile loop.

More Oregon Coast

A scenic way to extend this trip back to Portland would be to explore more of the Oregon coast. It’s a popular spot for Oregonians in the summer and each town has a different feel.

We already covered Cannon Beach and Astoria, but other popular spots are: Seaside, Lincoln City, Newport and Florence. 

Seaside reminds us of the charming coastal towns of Maine on the opposite coast of the USA. It’s pretty kitsch yet cute and makes a nice stop between Cannon Beach and Astoria. I would recommend spending the night in Cannon Beach though (they’re under 15 minutes from each other).

At Tilamook, you can stop at the famous Tilamook Creamery and learn more about the dairy making process and sample their wares.

Lincoln City is more developed than Cannon Beach, but still retains a rugged coastal charm. The beach is spectacular and the town has a peculiar niche of glassblowing. You can do glassblowing classes there, and they have a cool initiative called Finders Keepers where local artists hide 3,000 glass floats on the beach each year for people to find. 

Newport has the Oregon Coast Aquarium. And much further south, Florence has epic sand dunes for sandboarding, as well as a cute downtown.

Found this useful? Share it on Pinterest!

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.