Incredible 5 Day Oregon Roadtrip from Portland

During my travel nurse contract in Portland, Oregon, I made a point to see the best of Oregon and the Pacific Northwest. This 5 day roadtrip takes you through some of my favorite parts of Oregon.

Here is a snapshot of the roadtrip:

• Day 1- Drive to Roseburg, Oregon
• Day 2- Rogue-Umpqua Scenic Byway
• Day 3- Crater Lake National Park
• Day 4- Bend, Oregon
• Day 5- Back to Portland

If you have more days available for your roadtrip, this Oregon Coast Roadtrip adds another day or 2 to the start of your trip. You can also add in this day trip in the Columbia River Gorge right outside of Portland to really round out your Oregon experience.

Day 1- Drive to Roseburg, OR

Roseburg is roughly a 3 hour drive from Portland if you drive straight through. This is what my husband and I did because he had to work on this day. We left after he was finished with work, checked into our airbnb and went to dinner at the McMenamins Roseburg Station Pub and Brewery. Our main objective in choosing Roseburg was to position ourselves for the following days.

**Side note- If you’ve never heard of McMenamins, it’s a chain of pubs, breweries, hotels, and other venues in Washington and Oregon. They are known for repurposing historic buildings while maintaining their original style and history. Each McMenamins is different, and you should definitely check one out if you are visiting the Pacific Northwest**

If you have more time than we did on day 1, here are my recommendations:

• Salem, Oregon- Oregon’s capital located in the Willamette Valley known for parks, surrounding natural beauty and wineries.
• Eugene, Oregon- an outdoorsy, hippie college-town with lots of hiking and biking. This is the home of the Oregon Ducks.
• Roseburg wineries- While the Willamette Valley is known more for it’s wineries than Roseburg, choosing to go wine tasting in Roseburg will give you the option to check into your airbnb or hotel first then Uber or Lyft to the winery.

Day 2- Rogue-Umpqua Scenic Byway

The Rogue-Umpqua Scenic Byway is also known as Highway 138 or Oregon’s Highway of Waterfalls (not to be confused with the Columbia River Gorge Waterfall Corridor). It starts around 20 minutes east of Roseburg.

Be sure to pick up some food, snacks and fill up on gas before you leave Roseburg. Your options will be limited in the remote Umpqua forest.

This area is full of hikes, waterfalls and hot springs. Unfortunately, during our roadtrip, there was a forest fire nearby meaning that some of the spots we wanted to see were closed.

Here are some options for stops and hikes along the Rogue-Umpqua Scenic Byway. Toketee and Umpqua Hot Springs are two of the most popular options, but they are also two of the most crowded:

• Susan Creek Falls
  • 0.75 miles, easy
  • Located right off of Hwy 138
• Fall Creek Falls
  • 1 mile moderate-challenging
  • You can swim
  • Located right off of Hwy 138, around 16.5 miles from the town of Glide.
• Wolf Creek Falls
  • 1.25 miles each way on a easy to moderate out and back trail.
  • The trail has 2 small waterfalls with pools below where you can swim.
  • Turn off Hwy 138 onto County Road 17/Little River Road (near Glide). The trail is 10.7 miles ahead.
• Grotto Falls Trailhead
  • 0.5 miles, easy
  • Turn right off Hwy 138 onto County Road 17 (Little River Road). Continue 16 miles, then turn left onto Forest Road 2703 (Lookout Mountain Road). Continue 4.5 miles to Forest Road 2703-150. The trailhead is found 2 miles ahead.
  • This includes driving on gravel
  • Amount of water in the falls tends to drop off in late summer.
• Yakso Falls Trail
  • 1.4 miles, easy
  • Turn off Hwy 138 onto County Road 17 (Little River Road). Continue 20 miles until it becomes Forest Road 27 (gravel surface). You’ll find the trailhead and a campground 7 miles ahead.
  • This includes driving on gravel.
• Toketee Falls
  • This famous waterfall is one of the areas that was closed due to wildfires during my visit which was a major bummer! Hopefully you’ll be luckier than I was.
  • 0.4 miles each way out and back trail
  • Around 200 stairs
  • Turn off hwy 138 onto Forest Road 34 (Toketee-Rigdon Road)
  • Tends to be crowded
• Umpqua Hot Springs
  • This is another area that was closed due to wildfires during my visit.
  • 0.3 mile steep climb from the parking lot to the hot springs
  • Cost: $5 – You can pay on site through a QR code posted on their parking lot bulletin board, but cell service may be spotty. You can also pay with cash.
  • Turn off Hwy 138 onto Forest Road 34 (same as Toketee Falls). At the bottom of the hill, turn left on the concrete bridge. Continue 2.2 miles, then turn right onto Forest Road 3401. The parking lot is 0.7 miles ahead on the left.
  • Open sunrise to sunset (closed at night)
  • Tends to be crowded– parking can be difficult
  • Clothing-optional
• Watson Falls
  • Highest waterfall in Southern Oregon (Multinomah Falls is the tallest in all of Oregon)
  • 0.4 mile trail
  • Turn south off Hwy 138 onto Forest Road 37 (aka. Fish Creek Road)
  • Tends to be crowded

There are plenty more options for hikes and stops throughout the Umpqua National Forest. There are also several options for camping (including dispersed camping).

My husband and I opted to stay at a camping resort in the Umpqua National Forest called Umpqua’s Last Resort. We stayed in one of their camper cabins. The location was a perfect end to this day of the roadtrip and an easy starting point for our next day at Crater Lake. If you are interested in booking here, be aware that they do fill up fast. Also, the resort host is a great resource for tips on what to do and see in the area. This turned out to be really helpful when our plans were turned upside down by the forest fires.

Day 3- Crater Lake National Park

Crater Lake National Park based around a collapsed volcano (Mount Mazama) that formed the deepest lake in the United States. The clarity and deep blue color of Crater Lake make it stand out as a natural wonder. The park is located around 1.5hrs from Umpqua’s Last Resort. The park is covered in snow for much of the year. While it is technically open year-round, the roads and trails are often not accessible in the winter months.

Rim drive is the road that circles the lake offering awesome views all the way around. There are several hiking trails to choose from inside the park, but my favorite was the hike down to Cleetwood Cove. This hike is 2.2 miles, but it has a steep grade that is more difficult on the way up. The trail is rated as moderate. My husband and I brought swimsuits and enjoyed some time sunbathing on the rocks on the shore. Be aware that the water is ice cold even on the hottest days of the year.

In the middle of Crater Lake, you’ll find a little island called Wizard Island. The park offers boat tours to Wizard Island that start at the bottom of the Cleetwood Cove trail. My husband and I did not take the boat tour, but a few of my coworkers did and gave it great reviews.

For a more in-depth review of Crater Lake National Park, visit my other post here.

Day 4- Bend, Oregon

Bend is a fun, outdoorsy town located 2-3 hours from Crater Lake National Park and 3-4 hours from Portland. This high desert city is known for breweries, mountain biking, snow skiing (on the famous Mount Bachelor), rock climbing, and again surrounding natural beauty (a common theme in Oregon!).

My husband and I had our fill of the outdoors by this point, so we chose to bike along the city’s Deschutes River and explore Bend’s craft beer scene.

One great way to explore Bend’s beer scene is the Bend Ale Trail. For the Bend Ale Trail, the breweries are arranged in “territories”, or area with a concentration of breweries. By visiting all the breweries in a territory, you can win a prize. This was a super fun way to explore the city.

Day 5- Back to Portland

On day 5 of our Oregon roadtrip, we slept in before heading back 3-4 hours to Portland. If you want to add some more adventure into this day, you can add in a stop to the Columbia River Gorge or the Mount Hood area as mentioned in my other post with day trips from Portland.