Oregon Trails: 3 Hikes That Will Kick Your Butt (& Are Totally Worth It)

Drive through the Columbia River Gorge on a sunny Saturday and you can’t miss the lines of cars parked along Highway 30, bursting with hikers from Portland. Dozens of beautiful hikes are easily accessible from the Portland metro area, but don’t expect a peaceful hike away from throngs of hipsters on trails like Eagle Creek, Multnomah Falls, and even the formerly hidden gem of Dog Mountain.

For hikers tired of dodging dogs and small children along the more popular hikes, look beyond your ‘50 Best Hikes With 50 Miles Of Portland’ guide to one of these more challenging and much more rewarding hikes. These intermediate-level climbs will get your heart pumping and the view at the top will be well worth the effort. You won’t regret it.

Lost Lake Butte

View of Mt. Hood from the summit of Lost Lake Butte, May 2015

For the avid Gorge hiker that enjoys a pint or glass in Hood River after a sunny day hike, it’s worth the extra hour driving up Mt. Hood to Lost Lake. This is a stunning lake with arguably the best view of the mountain around (yes, better than Trillium!). Lost Lake is a private resort and campground with a quaint store, rustic cabins, and several loops of tent camp sites.

If you leave early in the morning from Portland you can set out on the climb up Lost Lake Butte and still return in time for a drink in Hood River or Cascade Locks. Or better yet, bring your overnight gear and set up camp lakeside — just make sure you don’t miss the stunning sunsets reflecting on the mountain!

Mt. Hood from Lost Lake Resort at sunset, May 2015

Lost Lake Butte is a four mile round-trip trek up one of the many buttes adjacent to Mt. Hood. If you keep your pace brisk, you’ll get an awesome cardio workout as you climb, ending at an overlook of Sandy Glacier. There are infinite amazing views of Mt. Hood, and this one certainly ranks toward the top.

Trail Head Elevation: 3600'

Summit Elevation: 4200'

Miles RT: 4

Difficulty: 6

Olallie Butte

Phew, this one is a butt kicker! Disclaimer: this might be the most difficult hike I’ve ever done. The incline alone is just shy of brutal, but it’s the elevation that will push you out of your comfort zone. Despite the physical and emotional challenge, the view of Mt. Jefferson from the top and the adrenaline rush from pushing myself to my limit was so worth it.

Mt. Jefferson from Olallie Butte, September 2014

Olallie Butte towers over Olallie Lake, which admittedly is not close enough to Portland for a day trip. However, this is one of the most pristine, stunning lakes you will ever camp at. (Just remember to bring your own water — it’s that primative!) Mt. Jefferson is the elusive gem of the Oregon Cascades, tucked just south of Mt. Hood and not easily accessible. Oallie Lake will get you about as close as you can get without cimbing the damn thing. Grab some friends and your camping gear and head on up — just be sure to warn them of the ass kicking that awaits!

You’ll find the trail head just up the road from the lake — plan to drive and park, since this hike doesn't need to be any longer than it already is! Warning: the trail starts on a rocky road following some power lines, and don’t miss the turn off to the right where the PCT crosses your path. If you’ve gone more than a few minutes along the power lines, turn around!

The trail is narrow and rocky at times but overall well traveled and easy to navigate. Now here’s the doozy: you’ll climb 2500' in 3.5 miles, starting at 4500' and quickly rising to 7000'. This is where the elevation comes in to play — take it slow if you start to feel the elevation affect your breathing. Believe me, if I can do it, you can do it! And when you hit 6000' and start cursing me, just remember, I promised it would be worth it. I didn’t lie.

Looking NW from Olallie Butte summit, September 2014

From the top of the butte you get a stunning view of Mt. Jefferson, Olallie Lake, and really cool burnouts dotting the pristine forest. To the East lies the Warm Springs Reservation (in fact, for a good chunk of the trail you’ll be on reservation land). Take a nice long break to enjoy the view and chug some water. Pictures won’t do it justice, so sit back and enjoy.

Trail head elevation: 4500'

Summit elevation: 7000'

Miles RT: 7

Difficulty: 9

Black Crater

Last but not least, let’s venture along Hwy 20 to Central Oregon. This is my favorite place to hike, whether on a long day trip or a long weekend. You’ll find Black Crater a few miles outside of Sisters, and the trail will lead you to one of the best views of the Three Sisters you’ll find. On a clear day, you can see all three Sisters, Mt. Washington, Mt. Jefferson, and even Mt. Hood — it doesn't get any better!

Looking South at the Three Sisters from the summit of Black Crater

Black Crater is similar in distance and elevation to Olallie Butte but vastly different in topography. I actually did these two hikes on back-to-back weekends and it was incredible to get views of the Cascades from the same elevation but different angles. Expect red lava rock and sparse Central Oregon pines instead of the lush evergreen mountain forests of Ollalie. You’ll also catch great views of lava flows coming down the adjacent mountains. But nothing beats the stunning vista from the top!

Trail Head Elevation: 4900'

Summit Elevation: 7250'

Miles RT: 7

Difficulty: 8

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