Take the Oregon Outdoor-100 Challenge

Take the Oregon Outdoor-100 Challenge

Pro tips for your own challenge to explore 100 scenic state sights

Written and photographed by Travis Hughes

The mark of a truly great adventure is when the memories outnumber the miles traveled. A few years ago, I embarked on a quest to see 100 of Oregon’s most scenic spaces. It took me just over three years to complete, and the memories will last a lifetime. As a lifelong Oregonian, I wanted to see Oregon’s iconic places, such as Blue Pool, Multnomah Falls, Crater Lake and Haystack Rock in Cannon Beach, but I also wanted to see the state’s lesser-known gems.

My final list included everything from crashing waterfalls and towering rock formations to mountain summits, stunning beach vistas, wind-whipped deserts and spooky caves.

Taking the Oregon Outdoor-100 Challenge requires some planning. Here are some tips I learned along the way.

Think outside the box

Every corner of Oregon is worth exploring for its contribution to the landscape. On the coast, venture to the sprawling, multi-limbed Octopus Tree near Tillamook, or travel about 30 miles south along the coastline to the eerie Neskowin Ghost Forest, where spruce trees look as if they are marching into the Pacific. Visit Thor’s Well in Yachats, and watch crashing waves thrust up into the air, then dramatically plunge below the surface. From there, take a five-minute detour up to the Perpetua Rock Shelter.

When the tides are right, explore the shipwreck Peter Iredale near Astoria or seek out the hidden sea cave at Short Beach just west of Tillamook.

Look high, low and below

To get the full scope of Oregon’s beauty, be willing to work for it. Dust off the hiking boots and gain some altitude by summiting South Sister near Bend, climbing God’s Thumb near Lincoln City and taking in a sunset atop McKenzie Pass at Dee Wright Observatory.

Take your adventure underground around Bend and Redmond in Central Oregon, exploring subterranean sights such as Skylight Cave. At Crack-in-the-Ground in Christmas Valley, hike below the earth’s surface into a large volcanic fissure.

Rock out

Oregon’s rock formations invite adventures from mellow to amped. In Bandon, get some face time in with Face Rock, which looks as if a giant reclining under the ocean is peeking his head out just above the surface. Nearby, find the shape-shifting rock known as Howling Dog or Wizard’s Hat.

At the Metolius Balancing Rocks in the Deschutes National Forest, rock spires have boulders precariously perched atop.

Southeast of La Pine, visit Fort Rock, Oregon’s earthen version of the ancient Roman Colosseum. The volcanic monolith rose up from a lake bed of the Ice Age.

North of Bend in Terrebonne, try rock climbing at Smith Rock State Park or check out Monkey Face along the Misery Ridge hike. My journey ended at the Pillars of Rome, rock formations which look like ancient painted columns. Paulina Falls, south of Bend, and Abiqua Falls, near Scotts Mills, are situated in spectacular rock amphitheaters sure to take your breath away.

Explore scenic byways, highways

Oregon’s scenic highways are pathways for adventure-packed road trips. Oregon has twenty-nine designated scenic byways and tour routes. Hole-in-the-Ground along the Oregon Outback byway and the Painted Hills, along the Journey Through Time byway, is a must.

Other highways that are goldmines for adventure, include Highway 138, which I dubbed the Highway to Waterfall Heaven. More than a dozen waterfalls are along the route, including Toketee Falls and Watson Falls. Expand your reach to those far-reaching corners such as Hells Canyon and the Wallowa Mountains in northeastern Oregon.

Think seasonally

Partake in adventures in all four seasons. In spring, waterfalls are rushing with snowmelt, making it an ideal time to visit Trestle Creek Falls east of Cottage Grove or the mighty Salt Creek Falls off Highway 58. Travel 130 miles southeast of Portland to witness Lost Lake disappearing down a lava tube.

Cool off at the ocean and explore Boardman State Park on the southern coast and Devil’s Punchbowl near Newport.

Take in autumn foliage in the Columbia River Gorge or at Silver Falls State Park near Salem.

Trillium Lake reflects Mount Hood, and in the winter, get your powder fix at resorts such as Willamette Pass, Mount Bachelor or Hoodoo.

Surprisingly, 100 outdoor adventures add up fast, because Oregon delivers. Once you’re done, get to work on your second 100, and you’ll likely cross paths with others doing the same.

Travis Hughes stands at the finish of his Oregon Outdoor 100 Challenge, the 100-foot high Pillars of Rome.
Travis Hughes stands at the finish of his Oregon Outdoor 100 Challenge, the 100-foot high Pillars of Rome.


  • Boca Cave, Willamette National Forest near Detroit
  • Opal Creek Wilderness, Willamette National Forest near Lyons
  • Hug Point, off Highway 101 near Cannon Beach
  • Cape Kiwanda, Pacific City
  • Twin Rocks, off Highway 101 in Rockaway
  • Umpqua Hot Springs, off Highway 138, east of Glide
  • Angels Rest, Columbia River Gorge near Bridal Veil
  • Bridge of the Gods, spans from Highway 84 to Washington’s SR-14
  • Three Arch Rocks, Oceanside
  • Terwilliger Hot Springs, Highway 126 between Eugene and Bend
  • Oregon Caves, off Route 46, 20 miles east of Cave Junction
  • Alvord Desert, Harney County, southeast of the Steens Mountains
  • Steens Mountain, Oregon’s southeast corner
  • Table Rocks, Jackson County, north of the Rogue River
  • Hobbit Trail, off Highway 101, north of Florence
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