Ultimate 10-Day Oregon Itinerary

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Last updated Jun 8, 2023

This 10-Day Oregon Itinerary is catered to winter visitors with the ability to rent a car. Oregon is just stunning in the winter, and between the coast and inland, you get to experience two completely different climates. Travel Oregon is a good website to check before your travel, not only because of the COVID restriction but winter travel restrictions as well.

This 10-Day Oregon Itinerary is focused on outdoor activities around Bend and Oregon Coast. Fly in and out of Portland, rent a car, and enjoy Oregon’s beauty and winter splendor for ten days. The highlights in this itinerary are Multnomah Falls, Crater Lake, Smith Rock, and the entire Oregon coastline.

Day 1 – Drive to Bend

After landing in Portland the drive to Bend is approximately 3 hrs. Instead of getting straight to Bend, if you have plenty of daylight left use this opportunity to drive on Historic Columbia River Highway. There are many scenic viewpoints, short and long hiking trails with breathtaking views of Columbia River and Washington state, and amazing Multnomah Falls.

10-Day Oregon Itinerary
Multnomah Falls | Ultimate 10-Day Oregon Itinerary

We suggest taking the rest of the road to Hood River for late lunch before heading down to Bend. Driving south on Highway 35 will provide great views of Mt. Hood. Once you merge on 26 south and closer you get to Bend on the west you will see amazing views of Cascade Mountain Range and on the east, you will see views of Oregon’s high desert. Hard to believe that two such different landscapes can be so close to each other.

By the time you get to Bend there may not be much daylight left for anything to do but to grab dinner and stock up on groceries if staying in AriBnB.

Day 2 – Tumalo Falls and Snowmobiling

Tumalo Falls are beautiful any time of the year, but during the winter waterfall can freeze and even if it’s not it has such a mystical feel to them. During summer you can park and take a short walk to the falls viewpoint however, in the winter the road is closed and is used as a hiking trail.

The road ramp is closed shortly after Beanwallow Rd splits from the Tumalo Falls Rd and doesn’t provide much parking space, maybe enough for 5 or 6 cars and you may have to wait for someone to leave. The hike to the falls and back is approximately 6.5 miles, a relatively easy hike next to Tumalo Creek.

Things To Do In Oregon
Tumalo Falls | Ultimate 10-Day Oregon Itinerary

In the afternoon you can schedule a snowmobiling tour. We booked our tour with Central Oregon Adventures for two hours which took us around Mt. Bachelor with stunning views for Mt. Bachelor, Broken Top, Sparks Lake, and the rest of Cascade Mountains. If you are not an experienced snowmobiler, we think the 2-hr tour would be more than enough. However, if this is a piece of cake for you, they also offer a 4-hr tour that would take you to Elk Lake, inaccessible otherwise during winter.

Cascade Mountains in Oregon

Day 3 – Crater Lake National Park

Even though Crater Lake National Park is approximately 2.5 hours south of Bend it is a must-do! Make sure you visit the lake on a clear day and if you need to rearrange your itinerary to accommodate that, it is worth it!

Visiting Crater Lake
Crater Lake National Park | Ultimate 10-Day Oregon Itinerary

The beauty of the Crater Lake cannot be put into words, you simply have to see it. The visitor center, café, and lodge may be closed for the season so bring food and water with you. There are hiking trails you can explore or just sit in one place and take in the beauty. For more on what to do at Crater Lake National Park in winter, you can check out our post here.

Days 4, 5 & 6 – Skiing Mt. Bachelor

Most people come to Bend to ski Mt. Bachelor in the winter. Even if you are not a skier, they offer beginner lessons and equipment rental.

But if you truly do not like skiing, you can go see Painted Hills or hike one or more of the Deschutes River trails.

Day 7 – Smith Rock State Park & Drive to the Coast

 Smith Rock State Park is only a 40-minute drive northeast of Bend and is definitely worth a visit. This park is a sanctuary of majestic rock spires that rise above the Crooked River in Oregon’s high desert. It is a world-renowned destination for rock climbers.

There are many hiking trails to enjoy the views of this sanctuary and its surrounding area. We enjoyed the Misery Ridge Loop, one of the most difficult trails in the park with an elevation gain of about 1100 ft and 4 miles long. It’s a rocky trail with steep switchbacks to the top and then once passed the Monkey Face Rock switchbacks down to the river, then a leisurely walk by the river to finish the loop. Keep your eye on the wildlife, we saw two bald eagles flying over us!

Hikes in Smith Rock
Smith Rock State Park | Ultimate 10-Day Oregon Itinerary

Other than hiking, there are a lot of rock climbers and mountain bikers visiting this park, as well as just locals with their pets coming out for a stroll.

After the hike, we stopped for a quick lunch in Redmond and got on the road to the Oregon Coast. Driving west you will pass through Cascade Mountain Range, right between Three Fingered Jack and Mt. Washington, national forests, and Coastal Mountain Range before getting a peek of the Pacific Ocean.

We completed our day’s journey by walking on the beach and enjoying the sunset.

Days 8, 9 & 10 – Oregon Coast

March may not be a perfect month for visiting the coast it is still very rainy, cold, and windy but we lucked out with most of the activities we wanted to do. To make it easier and limit the amount of driving we picked two different coastal villages to stay in. One on the central coast and one on the northern coast.

From the central coast, we drove south of Florence to Sand Dunes. These dunes extend for about 40 miles along the coast between Florence and Coos Bay and can be as high as 500 ft. The main attraction is renting some AVTs and riding on the dunes or you can choose to hike some trails or bike some trails.

Driving north from here make sure you check out Sea Lions Cave, Heceta Lighthouse, Thor’s Well, Spouting Horn, and Devil’s Churn. There are many viewpoints where you can stop, take a short hike and enjoy the views.

Oregon Road Trip
Thor’s Well | Ultimate 10-Day Oregon Itinerary

Next day we ventured off to one of the crazy hikes through mud, wind and rain, falling down and sliding on our butts for a view that took our breath away – God’s Thumb. For more information on this hike, you can check out our post Hike To God’s Thumb On a Rainy Day.

On our last day we drove north and enjoyed the scenic views of Cannon Beach, Ecola Park, and Astoria. Oregon coast is just stunning, you could pull over every 5 minutes to enjoy a different view.

Canon Beach

The next day we drove to Portland, through Coastal Mountain Range watching clouds move in and out, much like in Costa Rica, for our flight back.

Oregon is a beautiful and very diverse state, and we can’t wait for the next opportunity to see more of it, especially its wine country.

Other helpful posts…

Things To Do In Oregon In Winter
Winter at Crater Lake
Hike To God’s Thumb
Five Exquisit Wineries to Visit in Willamette Valley
2 Amazing Week in WA & OR – For Hikers and Wine Lovers
5-Day Road Trip – Zion, Bryce and Grand Canyon
The Best Hike in The Canyonlands – Chesler Park/Joint Trail Loop




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