Best Oregon Road Trip Itinerary for 7 to 10 days (2024)

I recently made a road trip across Oregon with my family and was mesmerized by Oregon’s untamed beauty!

Nestled in the Pacific Northwest region of the United States, Oregon offers a mesmerizing blend of rugged coastline, dense forests, cascading waterfalls, and bustling cities.

On our road trip, we covered the Oregon Coast from Canon Beach to Newport, explored the cities of Portland and Bend, awed at Crater Lake National Park, and marveled at the natural beauty of Columbia River Gorge, Smith Rock State Park, and Hood River.

Whether you are starting your Oregon road trip from California or Portland, I have detailed itineraries outlined in this post for both routes.

Let’s plan the perfect Oregon itinerary and get ready for an unforgettable journey through the heart of the Pacific Northwest!

Planning the perfect Oregon Road Trip Itinerary

You can do the Oregon Road trip two ways –

1. Flying into Portland city and making a loop road trip that starts and ends in Portland
2. If you are in Northern California (like me), start and end your Oregon road trip in California. I started from San Francisco Bay Area and did a loop Oregon road trip.

Oregon road trip itinerary from California

I live in the San Francisco Bay Area, and we did the Oregon road trip loop driving from California.

Below is our Oregon road trip itinerary from San Francisco Bay Area covering Bend, Hood River, Columbia Gorge and Multnomah Falls, Portland, Cannon Beach, Tillamook, Newport, and Ashland.

We went from Bend to Hood River and then to Portland. From Portland, we went west to the Oregon Coast and explored Cannon Beach, Tillamook, and Newport. Finally, we went inland to Ashland before driving back to California, thus completing our loop.

California to Oregon road trip itinerary for 7 to 10 days

• Day 1: Drive from San Francisco Bay Area to Bend, stay overnight in Bend
• Day 2: Explore Bend, stay overnight in Bend
• Optional day add-on: Day trip to Crater Lake National Park
• Day 3: Bend to Portland Scenic Drive, Hood River, Columbia Gorge, overnight in Portland
• Optional day add-on: Stay overnight in Hood River
• Day 4: Explore Portland, stay overnight in Portland
• Optional day add-on: Stay overnight in Cannon Beach
• Day 5: Explore Oregon Coast, stay overnight in Newport
• Day 6: Explore Newport, overnight in Ashland
• Day 7: Drive back to San Francisco Bay Area

We only had seven days for this route trip, so it was very jam-packed and involved a lot of driving. Driving from San Francisco Bay Area to the Oregon border itself takes around 5 hours one way.

If you have more time, I suggest adding a few more days to your road trip to allow additional days in Bend, Hood River, Portland, and the Oregon Coast.

Map of Oregon Road Trip Route from California

Click here to see the map of this route in Google Maps.

Oregon road trip itinerary from Portland

If you are flying in from another state into Portland, then your Oregon road trip itinerary will start and end in Portland.

You can drive first to the west of Portland towards the Oregon Coast or drive east towards Hood River and Bend, depending on accommodations availability.

Oregon road trip itinerary from Portland for 7 to 10 days

• Day 1: Arrive In Portland. Stay overnight in Portland.
• Day 2: Explore Portland. Stay overnight in Portland.
• Day 3: Drive from Portland to Oregon Coast – Cannon Beach, Tillamook. Stay overnight in Newport.
• Optional day add-on: Stay overnight in Cannon Beach and explore Astoria as well.
• Day 4: Explore Newport. Drive to Ashland. Stay overnight in Ashland.
• Day 5: Drive to Bend. Stay overnight in Bend.
• Day 6: Explore Bend. Stay overnight in Bend.
• Optional day add-on: Day trip to Crater Lake National Park
• Day 7: Bend to Portland Scenic Drive, Hood River, Columbia Gorge. Return to Portland
• Optional day add-on: Stay overnight in Hood River

Map of Oregon Road Trip Route from Portland

Click here to see the map of this route in Google Maps.

Extending Oregon Road Trip from 10 days to 2 weeks

10 to 14 days is the ideal duration for an Oregon road trip so that you have more days to explore and relax. With seven days, it will be a lot of driving each day and less time at each place.

We made this Oregon road trip from California in a week due to time constraints, and it was a lot of driving most days and less time for exploration. We were still able to see all the highlights and saved the hidden gems for future trips.

With only seven days, you will not be able to see everything and will have to pick only the must-do sights.

Also, there won’t be time to do some of the longer hikes, and you will have to stick to the short hikes or walks to the Vista points. Luckily, we found that all the popular attractions in Oregon are just a short walk from the parking lot.

Below are some suggestions to extend your road trip to Oregon beyond seven days:

• Visit Crater Lake National Park as a day trip from Bend or stay overnight in Crater Lake.
• Stay overnight in Hood River.
• Stay an extra day in Portland to explore the various neighborhoods.
• Explore Astoria and stay overnight in Cannon Beach (add a day here).
• Extend the Oregon Coast route further down Newport to Florence (add a day) or all the way to Brookings (add two days).

Places to explore on Oregon Road Trip

No matter which road trip itinerary route you choose, whether starting in Portland or California, below are the must-do stops and destinations on your Oregon road trip.

For each of these places, I have listed the top things to do there and accommodation suggestions for where to stay overnight.

Portland

If you are flying into Oregon for this road trip, then you most probably will start and end your road trip in Portland, which is the largest city in Oregon.

Plan to spend at least one full day, i.e., two nights in Portland or more. We reached Portland in the evening and stayed for two nights. This gave us a full day to see the sights in downtown Portland.

Top things to do in Portland

We had one day of sightseeing in downtown Portland, and below are some of the must-do sights in your Portland itinerary based on my research and experience.

You will need a car to see some of these places as they are a bit uphill, like the Pittock Mansion and Washington Park, but others are walkable if you stay downtown.

With just one day in Portland, I highly recommend taking a city tour if you want to make sure you can cover all the sights. Of course, you can also see the sights on your own by driving around.

➡ Check rates and availability for this Best of Portland Morning City tour or Best of Portland Afternoon City tour covers the top sights. Perfect if you have limited time in Portland!

Pittock Mansion

We drove straight to Pittock Mansion in the morning to see the famous city views. It’s only around 12 minutes from downtown by car. There is a small parking lot here with a fee.

This historic house museum sits atop a hill, providing stunning city views. You can explore its elegant rooms and learn about the city’s heritage through exhibits and artifacts.

The mansion has an entry fee, but it is free to explore the grounds and admire the views of downtown Portland.

Washington Park

Washington Park in Portland is a sprawling urban park offering diverse attractions like the International Rose Test Garden, Portland Japanese Garden, Hoyt Arboretum, Oregon Zoo, and Oregon Children’s Museum.

Situated to the west of downtown Portland, the park spans over 400 acres, providing a serene escape from the city’s hustle and bustle.

You would need a full day to explore Washington Park. With just a few hours, it is best to pick one of its attractions based on your interest.

We visited the International Rose Test Garden, as Portland is called the ‘City of Roses’. The rose garden is a very popular attraction here.

The rose garden had thousands of rose varieties blooming in vibrant colors during July. It was a huge and well-maintained rose garden!

Next time, we will definitely visit the Hyott Arboretum and explore the hiking trails in the urban forest. If you have time, definitely check it out.

Portland hip neighborhoods for dining

After exploring Washington Park, head to one of the cool neighborhoods in downtown Portland for a nice meal.

Northwest 23rd Ave Street is bustling with restaurants, cafes, and breweries. I loved strolling through the street and window shopping. We were in the mood for Thai cuisine and tried Thai Bloom restaurant. The food was great!

Pearl District in Portland is a trendy, urban neighborhood known for its artsy vibe, upscale boutiques, and diverse restaurants and cafes.

Powell’s City of Books

Powell’s City of Books in downtown Portland is one of the largest bookstores in the world and a must-visit while in Portland.

Powell’s occupies an entire city block and features multiple floors filled with an extensive collection of new, used, and rare books. The bookstore is so huge that they have a map of the various sections!

My entire family spent several hours here, and we left with a lot of books! Make sure to check out the Rare Books room on the third floor. It is really cool, and some of the books are really old and expensive here.

Waterfront Park

Enjoy a leisurely walk along the Willamette River waterfront and soak in the scenic views of the city and the nearby bridges.

Starting at the south end of Burnside Bridge, the Waterfront Park Trail goes on for miles and is ideal for strolling, cycling, or jogging along the Willamette River.

Note: There is quite a bit of a homeless population in downtown Portland, and you might come across them, especially near the waterfront area. During the daytime, we felt quite safe exploring downtown Portland.

Where to stay in Portland

We stayed at Hyatt Centric Downtown Portland and cannot recommend it enough! It was at the perfect location to explore all the top sights in Portland downtown. The hotel is new and very modern and has a restaurant onsite. It also has valet parking privileges for a daily rate.

But what we really loved about this hotel is the excellent and friendly staff here. Everyone we met was really awesome, with great customer service. We got a bed and breakfast rate and loved the made-to-order breakfast at the restaurant.

Oregon Coast

Being from California, we have driven along the scenic Pacific Coast Highway 1 many times, but I was equally excited to experience the Oregon Coast.

Before this trip, I had seen amazing pictures of Cannon Beach and Oregon’s famous lighthouses. Let me tell you that the Oregon Coast did not disappoint! It was beautiful and very scenic.

We tried to stop at most of the vista points along the way for some epic views of beaches and the Pacific Ocean.

We drove from Portland to Cannon Beach and then south along Hwy 101 to Newport on the same day for our road trip. We stayed overnight in Newport.

If you have an extra day, consider including Astoria, which is to the north of Canon Beach, and staying overnight in Canon Beach.

We did this particular Oregon Coast road trip in summer, but winter in Oregon Coast is equally beautiful, with coastal storms causing dramatic huge crashing waves, and a more secluded experience with fewer crowds.

Cannon Beach

Our first stop on the Oregon Coast was Cannon Beach. Cannon Beach on the Oregon coast is a beautiful coastal town known for its iconic Haystack Rock, a massive sea stack rising from the ocean.

The beach is expansive, with soft sands perfect for strolling, beachcombing, and enjoying breathtaking sunsets. There were plenty of people on the beach, even on a Wednesday morning in July.

It was a little windy on the beach, but being from Northern California, we are used to cold beaches. It’s best to dress in layers on your Oregon Coast road trip!

The Wayfarer Restaurant & Lounge is right at the beach for some seafood lunch.

Surfsand Resort is a family-friendly resort located right on the beach, offering comfortable rooms and excellent amenities.

Tillamook Cheese Factory

After Canon Beach, our next major stop on the Oregon Coast road trip was at the Tillamook Cheese factory. My teens were excited to see the factory and try the cheese samples and the famous ice cream.

Let me tell you that this was the most crowded place on the entire Oregon Coast as it is one of the most popular Oregon Coastal attractions. We had to park in the overflow lot on a Wednesday afternoon in July.

The factory offers self-guided tours to see the cheese-making process and sample various kinds of cheese. There are paid tours as well, but as we didn’t want to be timebound, we just did the self-guided tour.

The self-guided tour was great, and there were free samples of cheese and cheese curds. The cafe has some great lunch and snack options, and the deep-dish pizza was great.

Make sure to try the Tillamook ice cream! Tillamook is famous for its creamy, indulgent ice cream, available in a range of delectable flavors.

Treat yourself to a scoop or two in a waffle cone or cup – the perfect way to cool down on a summer day. They have some great flavors, including new ones that are not found in stores.

Three Capes Scenic Drive

Between Tillamook and Newport is the very scenic stretch of the Oregon Coast called the Three Capes scenic drive or loop. As we were headed to Newport, we did not do this as a loop but just as a one-way drive.

The Three Capes are Cape Meares, Cape Lookout, and Cape Kiwanda. After Tillamook, Hwy 101 goes inland, and you will have to take a detour on Hwy 131 and up Netarts and Oceanside to reach Cape Meares.

Cape Meares was my favorite as it has a cool lighthouse, a short walk over a paved trail from the parking lot. The trail has a slight downhill incline on the way to the lighthouse.

Another attraction at Cape Meares is the Octopus tree. There is a short dirt trail in a beautiful forest to reach it. It’s just 0.2 miles and an easy walk. The unique Sitka Spruce tree is estimated to be around 300 years old and 16 feet wide!

Cape Lookout State Park has a beautiful wide beach, campground, and hiking trails for some epic views. We just stopped at the Cape Lookout viewpoint for some panoramic views of Cape Lookout Beach and Netarts Bay.

Cape Kiwanda is at the northern end of Pacific City Beach. This cape is famous for its massive sand dune, known as the “Giant Sand Dune.”

You can climb the sand dune for panoramic views of the coastline and the surrounding landscape. We stopped at Pacific City Beach to admire the Cape Kiwanda sand dune.

After Pacific City, you merge back to Hwy 101 and continue South. There are several nice beach towns along the route, like Lincoln City and Depoe Bay if you would like to stop for food.

Newport, Oregon

Finally, after a long day of driving along the Oregon Coast and admiring some amazing coastal views, we reached Newport.

Newport, Oregon, is a coastal town known for its picturesque beaches, historic Bayfront, marine life, and Yaquina Head Lighthouse.

It is one of the larger towns on the Oregon Coast and a great place to stay for the night or a couple of nights.

Top things to do in Newport

Yaquina Head Lighthouse is the most stunning lighthouse on the Oregon Coast. From the viewpoint behind the lighthouse, we saw several whales spouting far off in the ocean!

There is an entry fee of around $7 to enter the Yaquina Head Outstanding Natural Area. There are several hiking trails here and beaches like Quarry Cove and Pebble Beach. The entire area is really serene and beautiful, with 360-degree ocean views.

Nye Beach is the most popular beach in Newport for strolling along the beach, watching the sunset, or dining at restaurants along the beach.

Newport Historic Bayfront is a bustling shopping and dining hub with seafood restaurants like Clearwater. Admire the views of the Yaquina Bay Bridge from the waterfront.

Oregon Coast Aquarium is a fun place to see marine animals like sharks, sea otters, and colorful fish.

Where to stay in Newport

Elizabeth Oceanfront Suites is a great place to stay in Newport with Oceanfront rooms. As we had only one night’s stay on the Oregon coast, I wanted an oceanfront room to get the full Oregon coast experience.

We got a large room with two king beds. It had a balcony with beach and ocean views and a fireplace! It was amazing to watch the sunset right from our balcony! I could see the lighthouse in the distance as well.

The Inn at Nye Beach is another great place to stay right on Nye Beach, with oceanfront rooms and a Spa. It also has breakfast and parking included.

Bend, Oregon

Bend is a great stopover in your Oregon road trip itinerary for a couple of nights. It is renowned for its abundant recreational activities and vibrant community. Bend has an amazing downtown in the Old Bend area and a newer Old Mill District.

We stayed two nights in Bend and really enjoyed strolling through the town, exploring the cafes, shops, and restaurants. We also did a half-day trip to visit the Smith Rock State Park for hiking.

There are some great day trips you can do from Bend, like Crater Lake National Park, Smith Rock State Park, and Hood River.

Top things to do in Bend

Floating the Deschutes River: During summer months, floating down the Deschutes River on inner tubes or inflatable kayaks is a popular pastime for locals and a must-do in Bend in the summer! It’s a relaxing way to enjoy the scenery and soak up the sun.

Old Mill District: A lively area with a charming riverfront, the Old Mill District offers shopping, dining, and entertainment. Enjoy a leisurely stroll, catch a movie at the cinema, or dine in one of the excellent restaurants. Our hotel was right next to Old Mill, and we enjoyed eating at Pastini and watching the people floating down the Deschutes River.

Pilot Butte State Scenic Viewpoint – In the evening I highly recommend hiking or driving to the top of Pilot Butte, a small volcanic mountain in Bend for some 360-degree panoramic views of Bend town and the surrounding mountain ranges!

Tumalo Falls: Take a short drive of around 30 minutes west of Bend to see the impressive Tumalo Falls. The viewing area is a short walk from the parking lot and offers a stunning vista of the cascading water. You can hike to the upper viewpoint of Tumalo Falls for a closer look.

Smith Rock State Park: Located just outside Bend, Smith Rock offers breathtaking rock formations and is a popular destination for rock climbing, hiking, and photography. The Misery Ridge Trail provides stunning views of the Crooked River Canyon.

Drake Park and Mirror Pond: Stroll through Drake Park, a beautiful park in the heart of Bend, and enjoy the tranquil scenery surrounding Mirror Pond. It’s an ideal spot for a picnic or a relaxing afternoon.

Bend Ale Trail: For beer enthusiasts, Bend boasts an impressive number of craft breweries. You can explore the Bend Ale Trail, sampling some of the finest brews in the Pacific Northwest.

Newberry National Volcanic Monument: This volcanic area in Deschutes National Forest is great for exploring unique geological features, such as lava tubes and obsidian flows. Take the park shuttle or hike to the top of Lava Butte for some excellent views of the caldera and the surrounding area.

Where to stay in Bend

Bend has quite a few areas where you can choose to stay. You can stay near the Old Mill District, near the Old Bend downtown, or a little further away from the main town.

The Oxford Hotel Bend is a great luxury boutique hotel right in the Bend downtown area and within walking distance to restaurants, shops, and Drake Park. Unfortunately, it was sold out for our travel dates.

Hampton Inn & Suites Bend is a mid-range hotel right next to the Old Mill District and Hayden Homes Amphitheater. This is where we stayed, and we loved the proximity to Old Mill dining and being able to walk on the trail along the Deschutes River. Great rooms, free breakfast, and parking. It also has an indoor pool.

Tetherow Resort is an upscale hotel with a golf course near the Deschutes National Forest. Great location for recreational activities like hiking in summer and skiing in winter. Has a pool and several restaurants onsite.

Bend to Portland (or Portland to Bend) Scenic Drive

Portland to Bend or Bend to Portland scenic drive is one of the best drives in an Oregon road trip. I liked this road trip stretch even more than the Oregon Coast drive.

To travel from Bend to Portland or vice versa, the scenic drive is the US-97N and US-26W route via Hood River and Columbia Gorge which is often called the scenic route.

Below are the stops we made along the Bend to Portland scenic drive:

• Smith Rock State Park – excellent for hiking and rock climbing
• Scenic Drive through Mount Hood National Forest along US-26 W
• Mt Hood
• Hood River and Hood River fruit loop
• Multnomah Falls
• Historic Columbia River Highway and vista points

If you are driving from Portland to Bend instead, do these stops in the reverse order starting with the Historic Columbia River Highway.

Smith Rock State Park

Our first stop in the Bend to Portland scenic drive was Smith Rock State Park. This iconic destination offers incredible rock formations and is a favorite spot for rock climbers and hikers. The views of the Crooked River Canyon are awe-inspiring.

Misery Ridge Trail is a challenging hike leading to the top of Misery Ridge, offering panoramic views of the Crooked River and Monkey Face rock formation.

For an easier short hike, try the River Trail, which is an easy trail along the Crooked River, perfect for a leisurely walk with beautiful views of the cliffs. We hiked this trail, but note that there is some elevation to get down to the river trail from the parking lot.

Hood River

Hood River is a great place to stop for a few hours or overnight on your Oregon road trip between Portland and Bend. Hood River is around 1 hour from Portland and around 3 hours from Bend.

Hood River is a mecca for windsurfing and kiteboarding enthusiasts. This charming town also offers excellent dining options, boutique shops, and stunning river views.

We just spent a few hours here, but Hood River is also a great weekend getaway destination. Next time we plan to stay here overnight for sure!

Top things to do in Hood River

At Hood River, you will find plenty of small businesses to explore, ranging from breweries, wineries, and produce farms. The riverfront town also offers plenty of water recreational activities.

Hood River Fruit Loop

Exploring the Hood River fruit loop is one of the top things to do in Hood River.

This self-guided tour takes you through picturesque orchards and farm stands, offering a taste of the region’s freshest produce, artisan foods, and delightful U-pick experiences during the harvest season.

We stopped at Hood River Lavender Farms, and it was so beautiful. I enjoyed picking a bouquet of lavender to bring home with me. Their store has a lot of high-quality lavender products like essential oils, bath and body products, and edible lavender to purchase.

Hood River Waterfront Park

This beautiful park along the Columbia River provides a perfect setting for picnics, kite flying, and relaxing by the water. The park offers stunning views of the Gorge and opportunities for waterside walks.

Windsurfing and Kiteboarding on the Columbia River

Hood River is a popular destination for windsurfing and kiteboarding enthusiasts. The consistent winds and stunning views of the Columbia River Gorge make it a paradise for water sports enthusiasts of all skill levels. It was fun to watch the kiteboarders from the waterfront park.

Visit Local Wineries and Taste the Region’s Wines

Hood River is part of the Columbia Gorge AVA, known for its excellent wines. Take a scenic wine tour and visit some of the charming wineries to taste a variety of wines, including award-winning Pinot Noir and refreshing white wines.

Relax at Hood River’s Craft Breweries and Enjoy Local Beers

Hood River has a thriving craft beer scene, with several breweries offering a variety of handcrafted beers. Relax on brewery patios, sample seasonal brews, and enjoy the laid-back atmosphere of this small town.

Downtown Hood River

Hood River’s downtown is a charming area with unique boutiques, art galleries, and craft stores. Here you can browse for local handmade items, artwork, and souvenirs and dine at the various restaurants.

Where to stay in Hood River

Hood River has a good mix of unique boutique hotels to familiar chain hotel brands, so you will definitely find something to match your needs.

Columbia Gorge Hotel and Spa is an excellent riverfront hotel with a spa, golf, and restaurant onsite. Get a room with views of the Columbia River! This hotel is in a quite location but minutes away from the Hood River town area.

Westcliff Lodge is a great place to stay, with views of the Columbia River and just minutes from the Hood River city center. The hotel has nice grounds and is pet-friendly.

Hampton Inn & Suites Hood River is at a great location within walking distance of Hood River Waterfront Park and the restaurants in Hood River city center. The hotel has free breakfast, free parking, and an indoor pool and hot tub.

Historic Columbia River Highway Scenic Drive

The Historic Columbia River Highway is a scenic drive that winds through the Columbia River Gorge in Oregon, offering breathtaking views of majestic waterfalls, lush forests, and dramatic cliffs.

The historic Columbia Gorge Highway is only a 40-minute drive from Portland and Hood River. The historic scenic highway runs parallel to _84 and has several amazing waterfalls and vista points along the way.

Multnomah Falls

Multnomah Falls is probably the most famous waterfall in Oregon! I had seen pictures of this cascading waterfall earlier, and it was on my bucket list!

Multnomah Falls is a two-tiered cascade totaling 635 feet in height. There is a main viewing platform for the lower-tier falls. A paved trail takes you to the Benson Bridge, providing a perfect vantage point to marvel at the falls.

The falls were spectacular, but the entire area was very crowded on a Monday afternoon in July. There was no space to stand on the bridge!

To park at the larger parking lot on I-84, you will need to make a parking reservation on the official Recreation.gov website. A permit is only required during the busy summer months from May to September.

There is a smaller parking lot on the historic Columbia River Highway that does not require a permit.

Note that you cannot drive directly between the two parking lots as they are on different roads which do not connect at Multnomah Falls. You will have to go a bit further up or down the historic highway to get on I-84.

Bridal Veil Falls

This graceful waterfall tumbles around 120 feet, resembling a bridal veil. From the Bridal Veil Falls State Scenic Viewpoint, you take a short hike through a lush forest that leads to a viewing platform, offering a picturesque perspective of the falls.

Latourell Falls

Latourell Falls cascades 249 feet over a striking basalt cliff. A short 1-mile hike from the highway takes you to a viewpoint where you can admire this magnificent waterfall up close.

Vista House at Crown Point

Vista House, perched on Crown Point, is a historic observatory, and the grounds provide sweeping views of the Gorge and the Columbia River below.

It’s a fantastic spot for photos and to admire the Columbia River and Gorge separating the Washington and Oregon states.

Portland Women’s Forum State Scenic Viewpoint

The Portland Women’s Forum State Scenic Viewpoint is an overlook that provides stunning panoramic views of the Columbia River Gorge, including the iconic Vista House at Crown Point and the majestic river below.

The viewpoint is named in honor of the Portland Women’s Forum, a group of influential women who played a significant role in advocating for preserving the Columbia River Gorge as a scenic area.

Crater Lake National Park

Crater Lake is the only National Park in Oregon and a must-visit in any road trip itinerary for Oregon.

I had made a separate trip to Crater Lake National Park before, so I skipped it on this trip, but if you have not been to Crater Lake, I highly recommend you make a day trip from Bend or stay overnight in Crater Lake National Park.

Top things to do in Crater Lake

Hiking: Explore the network of Crater Lake hiking trails, ranging from easy walks to challenging hikes, offering spectacular vistas of the lake and surrounding forests. I highly recommend the Cleetwood Cove Trail, which takes you to the lakeshore.

Boat Tours: During the summer months, take a guided boat tour on Crater Lake to experience the lake up close and learn about its geology and history. It was my favorite thing to do in Crater Lake. You can also visit Wizard Island on the boat tour.

Scenic Drive: Take a drive around the rim of the caldera for breathtaking views of Crater Lake from various vantage points, including Rim Village and Watchman Overlook.

Where to stay in Crater Lake

Crater Lake Lodge: Located right on the rim of the caldera, Crater Lake Lodge offers stunning lake views and a historic atmosphere. It’s the most iconic lodging option inside the National Park. This is where we stayed during our visit to Crater Lake.

Crater Lake Resort is just a 12-minute drive from the park and has multiple cabins with private bathrooms and furnished tents to choose from.

Ashland, Oregon

Ashland is the perfect small town to stop on your Oregon road trip, whether traveling between California and Portland or doing a loop road trip from Portland.

Ashland is around a 5-hour drive from both Portland and the San Francisco Bay Area, making it the best place to stop on your road trip.

When planning the road trip, I debated whether to stop in Medford or Ashland, but the charming downtown of Ashland seemed really nice. Also, there are some really nice bed and breakfasts in Ashland.

Also, I found this amazing boutique hotel in Ashland downtown – McCall House Boutique Inn. Staying in this preserved historic Inn built in 1883 was the highlight of our trip.

Top things to do in Ashland

Oregon Shakespeare Festival: Ashland is famous for the Oregon Shakespeare Festival. Watch world-class theater performances in beautiful outdoor venues. We were lucky to catch an outdoor performance happening on the evening of our visit.

Lithia Park: A beautiful picturesque park right in the middle of the town with gardens, walking trails, a creek, and a duck pond.

Ashland downtown: Ashland has a Hallmark movie-style charming downtown with restaurants, art galleries, boutiques, and shops.

Where to stay in Ashland

We stayed at the historic McCall House Boutique Inn. It was at the perfect location, and we could walk to the Oregon Shakespeare Festival, restaurants, and Lithia Park.

The house itself was beautifully renovated with all modern amenities inside. The rooms have unique decor, and the freshly prepared breakfast was delicious.

Lithia Springs Resort is another great place to stay in Ashland, off Interstate 5 and within a 5-minute drive to downtown Ashland. This resort has a pool, hot tub, and spa treatments for relaxing and rejuvenating.

Travel Tips for planning your Oregon Road Trip

Below travel tips and FAQs will help with planning your Oregon itinerary.

Where to start an Oregon road trip?

If you are flying into Oregon, Portland is the best place to start and end an Oregon road trip. Portland International Airport (PDX) serves major cities in the United States.

If you live in Northern California, you can start your road trip from your city. I started my road trip from San Francisco Bay Area. Keep in mind that it takes around 5 hours to drive from Northern California to the Oregon border, so that will add to your driving distance.

If you live in Southern California, flying into Portland for an Oregon-only road trip might save on the driving time across California, but it will add the expense of flights and a rental car.

How many days are needed for an Oregon road trip?

The suggested Oregon road trip itinerary can be completed in around 7 to 10 days, depending on the pace of your exploration and the number of stops you choose to make along the way. I recommend planning at least ten days so that you can spend more time in each place, as seven days was a bit rushed.

Do you need a rental car for an Oregon road trip?

Yes, if you are flying into Portland, you will need a rental car for this road trip, as most of the places on the road trip are best explored by car.

➡ I recommend using Discover Cars as they check top car rental brands and provide the best rate!

Which is the best season for an Oregon road trip?

The ideal time for an Oregon road trip is during the summer months (June to August) when the weather is generally pleasant, daylight hours are longer, and outdoor activities are abundant. However, spring (April to May) and fall (September to October) offer milder weather and fewer crowds, making them excellent alternatives.

What should I pack for an Oregon road trip?

Pack comfortable clothing suitable for various weather conditions, including layers, as weather can change quickly. Don’t forget essentials like sunscreen, insect repellent, sturdy footwear for hiking, and a phone/camera to capture stunning landscapes.

Can I camp along the route?

Yes, there are numerous campsites and RV parks along the road trip route where you can enjoy the beauty of Oregon’s nature up close.

Is it safe to drive in Oregon during winter?

Winter driving in Oregon can be challenging due to snow and icy conditions, especially in higher elevations. It’s essential to check weather forecasts and road conditions before embarking on a winter road trip and to have appropriate winter tires or chains.

Wrap-up: Oregon itinerary

With this Oregon road trip itinerary in hand, you’re all set for an unforgettable adventure. Embrace the scenic beauty, explore the charming towns and cities, and immerse yourself in nature’s wonders.

Whether it’s the rugged coastlines or the enchanting forests, each stop in Oregon promises something unique. So, pack your car, hit the road, and get ready to create memories that will last a lifetime.

More about Oregon

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7 Best Bed and Breakfast in Ashland, Oregon

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