Skip to main content

Oregon Road Trip: A Wilderness Escape

Beach bonfires, moonlit paddles, and rock climbing await on this week-long road trip from forest to coast.

Old-growth forests, high desert landscapes, snow-capped mountains, rolling vineyards, and rugged coastline make Oregon a dream destination for lovers of the outdoors. All Roads North has curated an activity-packed luxury nature vacation that showcases three very different parts of the state. “It’s pretty special to be able to see the Pacific Coast, high desert and the Columbia River Gorge in such a short time period,” says All Roads North founder, Sam Highley. “A variety of excursions, from rock climbing and canoeing to rafting and e-biking, make this the ideal trip for active families. There’s something for everyone.”

Your private vacation begins with a scenic drive from Portland along the Historic Columbia River Highway, a narrow, winding road edged by thick forest and steep cliffs, on the right and the mighty Columbia River on the left. This route is famous for its plentiful waterfalls, so build in time to hike to a few of the misty cascades, especially Multnomah Falls. Oregon’s tallest falls, Multnomah’s waters plunge a dramatic 542 feet. The beautiful Bridge of Gods crosses over the Columbia River, delivering you from Oregon to Washington, where you’ll settle into your cabin at Society Hotel Bingen. This boutique hotel has an unparalleled location nestled within the Gorge, plus a café serving Portland’s signature coffee, Stumptown, and a new spa with saltwater pools.

Private whitewater rafting trip along the White Salmon River
Bike to local vineyards and farms

All Roads North has built in curated travel experiences suited to every adventure threshold. If you’re craving an adrenaline rush, spend the following afternoon on a private whitewater rafting trip along the glacier-fed White Salmon River. If you prefer to stay dry, you can join a guided e-bike or road bike tour along a car-free section of Historic Highway 30, stopping at orchards and vineyards along the way. 

On day three you’ll cross back over to Oregon. Towering firs give way to orchards and farms as you ascend the pass over the Cascades into Central Oregon’s High Desert region as you make your way to Bend. All Roads North has put together bucket list travel adventures that underscore why this charming mountain town is known as America’s adventure capital. On your first evening, you’ll canoe along the calm waters of an alpine lake by the light of the moon. The following morning, a private climbing guide will take you up family-friendly routes at the birthplace of American rock climbing, Smith Rock State Park.

Your luxury private travel experience ends with three days on Oregon’s unspoiled coast. Headlands Lodge welcomes Members with a private beach bonfire on Pacific City Beach their arrival evening. This area boasts countless options for spectacular coastal hikes and All Roads North has organized special hands-on activities that immerse Members in coastal living. Get out on the water with a local fisherman or search for grey whales in Depoe Bay on a private zodiac tour with a marine expert. Wake early to don waders and rake for clams with a local guide in the waters of Netarts Bay. Your efforts will be rewarded back at the lodge, where the chef will transform your harvest into a clambake lunch. If you have time on your final day, take the longer route back to Portland along the Three Capes Scenic Loop, one of the most picturesque sections of the coast in the state.