48 Hours in Oregon: Your Epic Road Trip Itinerary

All Roads Lead to Untamed Beauty in Oregon

It's hard not to smile when you recall those memories of the highway stretching endlessly in front of you and the asphalt shimmering in the heat like magic. Trying to keep up with the trees as they racing by in a verdant blur, coupled with the feeling of the warm wind blustering between your fingers and hair as you peer out the car window, watching the world go by.

For those touched by wanderlust, there’s nothing like a summer road trip — the freedom of the wide, open road mixed with the thrill of the possibilities that await you at the next exit. Sandwiched between majestic mountains, lush rainforests and wild, white sand beaches, Portland is perfectly located for an adventurous road trip that will show you all the untamed beauty of Oregon.

Day 1 – Hiking Beacon Rock, Farms & Wineries in Hood River & Camping at Trillium Lake

START at Hotel Lucia. Fortify yourself for a long day behind the wheel with an delightfully eggy breakfast sandwich from Fried Egg I’m in Love in Pioneer Square, a couple blocks from our front door.

On clear, sunny days, Portlanders like to say, “The Mountain is out!” This refers to the fact that you can see big, beautiful, snow-capped Mt. Hood whenever the weather cooperates. Head east on I-84 towards “the Mountain,” and enjoy the view.

After about 45 minutes, you’ll reach the Bridge of the Gods, a toll bridge that connects Oregon to Washington over the Columbia River, and a section of the Pacific Crest Trail made famous by Reese Witherspoon in the movie “Wild.” If have 30 minutes to spare, you can cross the bridge to Washington, into Beacon Rock State Park, and hike to the top of Beacon Rock – 57,000 year-old plug of volcanic cinder cone – for breathtaking views of the Columbia River Gorge.

After some bracing exercise, you’ve probably picked up an appetite for lunch. Head on east on the Lewis and Clark Highway until you reach the town of White Salmon, then you’ll cross the Hood River Bridge back to Oregon. A quaint and welcoming riverfront city, Hood River is full of restaurants, breweries, distilleries, and boutiques. Our personal recommendation is Solstice Wood Fire Cafe, offering waterfront patio seating and delicious pizzas topped with creative and locally sourced ingredients.

Next, head out on either OR-35 or OR-281, the two legs that make up what is colloquially known as “the Fruit Loop,” the circle of Hood River farms and wineries where you can pick fruit, taste wine, sit, and gaze at peaceful pastoral views or simply make a quick pit stop at a roadside shop for farm-fresh sweets and snacks. We recommend stopping at The Gorge White House Fruit Stand Winery for amazing views and a glass of wine (for anyone not driving), Packer Orchards Farm Place for the best fresh hand pies and cookies in Oregon, and Draper Girls to pick up some jars of marvelous homemade jams. Take a moment to feed the charming resident goats, too.

Keep driving south down OR-35 as “The Mountain” grows in your windshield —eventually you’ll start scaling Mt. Hood, and the air will cool, and the scenery will fill with the dark green of those fantastic Douglas firs that Special Agent Dale Cooper loves so much. After about an hour of this perfectly pleasant drive, you’ll reach Trillium Lake and its namesake campground. Set up camp for the night, roast dinner (and marshmallows!) over the fire, and sleep under the stars at 3,600 feet.

Day 2 – Cozy Drive Ins & Blackberry Picking Along the Sandy River

The next morning, you can swim or fish in Trillium Lake, hike around one of the many trailheads nearby, or hop back in the car and head back to Portland.  Stop in Cascade Locks (where the Bridge of the Gods is, but on the Oregon side this time) for some memorable soft serve or classic diner-style cheeseburgers, served to you in your car, retro drive-in style at East Wind Drive-In. This trusty roadside standby has been around since 1939, and their thick, yummy shakes and incredible views keep road-trippers coming back.

Just before you get back to Portland, take exit 18 toward Oxbow Park. Follow the signs to this magical riverfront park, where you can hike, pick wild blackberries and, most importantly, swim in the calm, mostly shallow Sandy River, a popular cool-down spot for locals.

You’ve probably worked up quite an appetite catching rays and treading water, so follow the Historic Columbia River Highway for about 9 miles to Sugarpine Drive-In, an absolutely adorable drive-in restaurant perched on the banks of the Sandy River boasting a mouthwatering menu full of fresh and flavorful ingredients, spectacular sundaes, frosty adult beverages (which you can enjoy on the patio), and plenty of allergy- and vegan-friendly options.

Now that you’re tanned, stuffed, and sleepy, END your trip back at Hotel Lucia. If you wanted to put your feet up and order a room service cocktail (or two) or some soulful, wood fire grilled cuisine from Imperial, we wouldn’t blame you. You just knocked down a pretty eventful itinerary.