Best Oregon Road Trip in Under 100 Miles

The best Oregon road trip would not be complete without visiting one of the 7 wonders of Oregon, Crater Lake National Park. In under 100 miles you can see why this epic road trip makes Oregon one of the most interesting places for outdoor adventures and hikes. Starting at Crater Lake we cover my favorite road to cruise (Highway 138). Along this Scenic Byway there are multiple waterfalls that aren’t the over terrorized Multnomah Falls. This trip is great for those who want to make the most out of a limited amount of time. By far one of the best drives in Oregon. It including old growth forests, secluded views, wildlife, and all the natural wonders that make Oregon unique.

Crater Lake National Park

Crystal clear Crater Lake on a gorgeous summer day.

Definitely a must see for anyone who enjoys being small and feeling one with the earth and what not. This park offers stunning views from just about every angle. Cloudcap is the highest paved road in Oregon and reaches 8,000 feet. There are many lookout spots along the 33 mile rim drive that circles around the entire lake. Be sure to go in the summer because fall and winter offer harsh winds and brtual snowstorms. This would be great to take a snow mobile for a winter weekend getaway.

Crater Lake Sunset from the East Rim drive

It doesn’t get any better than the deepest lake in The United States at sunset.

Don’t forget Deet. The mosquitoes are bigger and badder than you have ever seen.

From there we head North out of the park to Highway 138. The good thing about Oregon is there aren’t a million established roads and there is only one way in and out coming from or heading North.

16 miles North hopping on Highway 138 will take you to Clearwater Falls which is past Diamond Lake. You can stop here but be prepared for overcrowded camping in the summer and over priced food from the local store. Not to mention the hoards of mosquitoes in the summer. Make sure to stock up on supplies or be prepared for hit to your wallet.

Clearwater Falls

Clearwater Falls

The entrance might sneak up on you and you might pass it if you don’t keep an eye out for the entrance on your left.

Take LEFT National Forest Development Road 4785/Clearwater Falls Campground

I enjoy this waterfall because it is only 50 yards or so from the parking lot and is easily accessible for most. It is well maintained but to get this view I went down past walkway. There are trails everywhere making the Umpqua National Forest an exciting playground that is easy to fall in love with.

From there we CONTINUE ON HIGHWAY 138 W 

10.6 miles to Watson Falls.

There are signs everywhere but the roads are windy and turns sneak up on you with haste.

Watson Falls

Watson Falls Oregon

The size and feeling that is Watson Falls. This is what heaven wants to look like. It’s calming and powerful while being serene with grace.

Take LEFT on NF 37 about 500 FEET SOUTH to the parking lot.

Watson Falls Oregon Highway 138

From there the trail is across NF 37. This place is at full potential in the early morning hours right before sunrise. It smells like peace on earth and if you are lucky you might be the only one at this location. Covered in moss a quick 1/3 mile trek slightly uphill takes you to the cathedral.

It feels like a fairy tale standing beneath an almost 300 foot wall of naturally gold, silver, green, running, flowing veins of Mother Earth. It doesn’t make sense all the time how structures like could form but it sure is amazing to take in their sights and sounds.

With a short few mile drive to Toketee Falls the trip keeps rollin, rollin, rollin, rollin, what.

HEAD WEST HIGHWAY 138 2.8 miles 

Toketee Falls

Toketee Falls Oregon

Another must see just in a short stretch. Although this place has gained popularity on Instagram and is featured on every moody profile (whatever the hell that means), I feel that if you are in the area it is worth it. The short hike to the main overlook offers beautifully shaded flowing streams with gigantic rock formations thrown everywhere is disarray.

After probably passing families and stoners on the trail if you go in summer, you will reach a point where you can be a bad ass and walk down to the fall or stay on the walk way and not risk injury. As for me being the slacktivist that I am, I chose to look it from up top and then go have beers by the river, where I lived.

From here you drive of course WEST 138 for 32.7 MILES to

Susan Creek Falls

Susan Creek Falls

The parking lot will be on your left (NORTH) and there is a pit bathroom there that smells really bad and probably doesn’t gets more use than the trails. Either way still a great place to walk about a mile or so. There is a beautiful foot bridge that opens up to this magical waterfall.

The Umpqua National Forest has that feeling of bliss and excitement every inch of it’s woods. There are some places that just feel good. Arkansas is not one of those places. Don’t go to Arkansas.

At this point that brings us to:

From The North Entrance of Crater Lake

65.1 miles of driving on Highway 138

1 Hour & 35 Minutes Driving Time 

of course that time is not including stopping and smelling the roses.

There are multiple more hikes, trails, and waterfalls along that stretch but those are the easiest and most accessible for people of all ages. They are all so close together which makes for a fun day or even week to get lost in all the enchanting limbs of this forest.


What are your favorite places that aren’t ruined yet? 



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One Reply to “Best Oregon Road Trip in Under 100 Miles”

  • It looks amazing! Not sure about what I would change. Love the pics and time line. That is huge for a spontaneous easily distracted person. Let’s me know how late I will be!!

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