The Ultimate Oregon Road Trip

In Collaboration with Backcountry


It’s All In the Journey

The concept of time and place as we experience them in our everyday lives doesn’t exist on the road.  The billable hours and routine that generally define our existence fades into the rearview mirror with each passing mile. Nights blur by like the oncoming headlights defining them. Structureless days stretch out along the road, promising nothing but boundless possibilities. Everything is new. You never really know exactly where you are. Or where you are going. You are free to experience life from a new perspective. To focus on the journey rather than the destination. It’s all pretty awesome when you think about it. 

With its long stretches of empty roads and accessible natural beauty, few places are more suited to road tripping than Oregon. And there’s no better time to experience the journey than fall. Warm beverages, good music, and the cozy interior of the car are the status quo. Only brief missions into the crisp pine scented air to stretch your legs and embrace stunning scenery interrupt the road’s flow. Heart full, soul satiated, you are ready for the next leg of the adventure. 

“Nothing behind me, everything ahead of me, as is ever so on the road.”  - Jack Kerouac, On the Road 

Oregon Bucket List Destinations

There is no wrong direction in Oregon. The more lost you get the better. Expectations have no place on the road. But a little inspiration never hurt! These are the destinations that keep me coming back for more. Hopefully they will awaken your wanderlust as well, and set your wheels in motion! 

The Columbia River Gorge

For sheer concentration of stunning scenery within close proximity to a bustling metropolitan area, you’d be hard-pressed to find anything that comes close to The Gorge. Don’t forget to bring your sense of adventure - the Gorge is made for exploring! Discover dozens of awe-inspiring waterfalls along the Historic Columbia River Highway, admire the Rowena Crest, and get your heart pumping on a trek up Dog Mountain.

Pro Tip: Some areas of the Columbia River Gorge were impacted by the Eagle Creek fire of 2017. Before you head out, learn more about what’s open and closed on the Historic Columbia River Highway and check with USFS for the most up-to-date information on trail closures.


Mount Hood

No trip to Oregon is complete without enjoying the epic drive between Mount Hood and the town of Hood River. While the mountain is a popular destination year round, fall offers the perfect combination of accessibility and solitude. Sparkling alpine lakes including Lost, Trillium and Mirror dot Mount Hood’s flanks. Each offer their own inspiring views of the mountain, and on a calm morning the reflections will take your breath away. 

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Abiqua Falls

Abiqua Falls is arguably my favorite waterfall in Oregon. The 92-foot waterfall is perfectly framed by an enormous basalt amphitheater adorned with bright green moss and lichens. But what makes the hike to the classic cascade so special is the approach. A rough trail through verdant forest takes you steeply down to the river bed, and then along the river until it terminates abruptly at the falls. 

Pro Tip: The hike down to the river bed is steep and can be treacherous when wet. Please use extreme caution.  It’s also important to remember that Abiqua Falls is located on private property owned by the Mt. Angel Abbey and Longview Timberlands. They have generously allowed the public to have access here, and this generosity demands the utmost respect for the land. 


Silver Falls State Park

Silver Falls State Park is the “crown jewel” of the Oregon State Parks system, and once you visit, you know why. Its beauty, boundless recreational opportunities, and historic presence are hard to beat. Ever wanted to walk behind a waterfall? Check out the South Falls and experience a 177 foot curtain of water from the inside. It’s part of the Trail of Ten Falls, a beautiful trail that traverses through a spectacular forest landscape. 

Silver Falls

Smith Rock State Park

Located in central Oregon’s high desert, Smith Rock State Park feels distinctly out of place in this predominantly green state. But that only add’s to it’s appeal! Famous for its climbing opportunities, Smith Rock also features some worthwhile hiking trails and some killer camping spots. Don’t miss Misery Ridge, the views at the top easily eclipse any pain experienced on the way up! 

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Crater Lake National Park

Home to the deepest lake in America, and Oregon’s only National Park, Crater Lake National Park is nothing short of otherworldly. With deep blue waters surrounded by 2,000 foot high cliffs, and punctuated by a picturesque island, there’s literally nowhere else on earth quite like it. 

Pro Tip: A good place to begin your visit to Crater Lake is at one of the two visitor centers.

Umpqua Hot Springs

A brief hike leads intrepid soak seekers to multiple pools perched above the North Umpqua River. Soak in the hot springs, enjoy the views, and cool off in the river below. Nudity is the norm here, so be mindful of others when taking photographs. 

Pro Tip: Umpqua Hot Springs has been shut down in the past due in part to excessive amounts of refuse, including human waste left by campers. Leave it better than you found it! 

Swim Suit:  L Space

Swim Suit: L Space

Toketee Falls

Located just down the road from Umpqua Hot Springs, Toketee Falls is arguably the most stunning waterfall in Oregon.  Framed by visually pleasing columnar basalt formations, and terminating in a bright blue pool surrounded by mist, Toketee is nothing short of magic. 

Swim Suit:  L Space

Swim Suit: L Space

Tamolitch Blue Pool

Located on Oregon’s famous McKenzie River Trail, it’s safe to say that you’ve probably never seen anything quite like Tamolitch Blue Pool. The water is so clear, so blue, that it resembles something closer to Scope mouth wash than anything you’d find in nature. A word of caution, the water is extremely cold! Do not get in unless you are confident with your ability to get out, and have the ability to dry off and quickly warm up afterwards. 

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Terwilliger (Cougar) Hot Springs

Located deep beneath the canopy of a primeval forest, Cougar Hot Springs features a chain of jewel colored pools fed by a small cave in a wooded ravine. Easily the most picturesque hot springs I’ve ever been to, Cougar understandably holds a very special place in the hearts of many. So much so, that I hesitated to include it in this list. But I trust that together we can keep this remarkable location preserved for generations to come. 

Pro Tip: Due to the Terwilliger Fire Cougar Hot Springs is currently closed. The state of the hot springs and any plans for reopening are unknown.

Cougar Hot Springs


Stunning ocean vistas, spiraling sea stacks, wild woods and pristine streams make the picturesque town of Bandon one of the Oregon Coasts most photographed locations. 

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Samuel H. Boardman State Scenic Corridor

Isolated on the southernmost corner of Oregon’s windswept coastline you will find Samuel H. Boardman State Scenic Corridor. In a state renowned for it’s awe-inspiring coast, Samuel Boardman stands out as the prettiest stretch. Wild and rugged, it’s a place you’ll find yourself daydreaming about long after you’ve left. 

Pro Tip: If you’ve made it this far south, make sure to drop down into California to check out Jedediah Smith Redwoods State Park. It will blow your mind.

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Leave It Better Than You Found It

There is little question that social media plays a role in exposing various outdoor locations, and in some cases, has led to significant resource and social impacts. And there is perhaps no place where this is more so than in the Pacific Northwest. That being said, I personally believe that without a connection to nature, people are much less likely to stand up and protect these beautiful natural wonders. For that reason, I have chosen to share some of my favorite locations in Oregon.

It is my deepest hope that you will visit these beautiful places and feel inspired to act as stewards for them well into the future. As part of this responsibility it’s important to keep in mind “Leave No Trace” principles whenever we enjoy the outdoors. Leave No Trace is built on seven core principles that outline the best available minimum impact guidance for enjoying the outdoors responsibly. These guidelines are not black or white, right or wrong. And they are certainly not about exclusion. Leave No Trace is a framework for making good decisions about enjoying the outdoors responsibly, regardless of how one chooses to do so. For more information please visit The Leave No Trace Center for Outdoor Ethics

© 1999 by the Leave No Trace Center for Outdoor Ethics:

Fall Road Trip Style Essentials

Packing for that road trip lifestyle can be a little tricky. You have to plan for a wide variety of different activities and conditions, while keeping in mind that space is limited. This is especially true as fall often brings significantly chilly nights and a lot more rain in the Pacific Northwest. But not to worry, with a few key items you can stay warm, dry, and still manage to look like you’re not living out of a car. The key is layering!

To help you gear up for all your fall adventures, I've partnered with Backcountry to offer 15% off your first purchase! Just use code JESS15 at checkout. (Some exclusions apply. Good through 12/31/18). Below are some of my personal favorite items!

Casual Jacket



Boots & Shoes

Please note that some of the links above are affiliate links, and I may earn a small commission on any purchase made - at no additional cost to you. As always, all ideas and opinions expressed in this post are entirely my own. Thanks for your support!

Photos in collaboration with Quin Schrock.