An Oregon Road Trip: Outdoor Adventure and Quirky Portland

Stretching along the banks of the picturesque Willamette River, Portland is a green, gourmet and trendy city that has signs of its young and creative population stamped across the city. It is also considered one the nation’s most liveable (and loveable) cities, thanks to its eclectic mix of well-designed parks, trendy shopping enclaves and charming residential districts. Today you’ll be discovering the Downtown and Pearl District neighbourhoods in the company of a local guide who knows the city like the back of their hand. They also happen to be quite the culinary enthusiast, so there’ll be a foodie feel to the tour throughout, with stops to discover local craft breweries, street food trucks, talented chefs and local artisans.

It’s time to bid farewell to the city and get some miles under your belt on this grand tour of Oregon. After breakfast this morning, collect your rental car and drive two hours west through pristine forested landscapes to Astoria, a historic city perched on the northwest coast. Your home here for the next two nights is an elegant and contemporary hotel overlooking Columbia River. Once you’ve settled in and freshened up, head out to enjoy the scenic and historic delights of the city and its coastal surroundings. The old part of town is anchored in its maritime history: you can visit the fascinating Columbia River Maritime Museum and tour Fort Clatsop, which once housed the famous American explorers Lewis and Clark. There are also a collection of beautiful beaches in easy driving distance, so we recommend rounding off your day with a late afternoon stroll along the shoreline.

This morning you’ll be boarding the fully-restored Arrow No.2, a vintage tugboat which made thousands of trips on the Columbia River from 1962 to 2012. Tugboats are very powerful small boats used to guide, pull and push the larger boats in and out of the port. The Arrow No.2 has become something of a legend in the region, thanks to its years of service supporting imposing boats and barges in their docking manoeuvres. This small-group river cruise is a great way to soak in the scenic delights of the region while learning about Astoria’s fascinating maritime history. Once you’re back on dry land you have options: you can continue exploring the city at your own leisure, or we can arrange for you to enjoy a private surfing lesson at Cannon Beach.

Your Oregon road trip continues today with a three-hour drive south along the wild Pacific Coast to Depoe Bay, the smallest navigable port in the world. There are plenty of long, sandy beaches worth stopping at along the way, including Cannon Beach, Arch Cape and Nedona. You could also make a stop at Tillamook, the dairy capital of Oregon, home to a huge cheddar cheese factory; the small town of Pacific City with its sweeping sand dunes; and Lincoln City, which is renowned for its wind and kite art. On arrival in Depoe Bay, check in for the night in an elegant and eco-oriented hotel overlooking the port and spend what you have left of today exploring the beautiful town centre. If you fancy getting straight out on the water, we could also arrange for you to head out on a whale-watching adventure in a Zodiac.

After breakfast this morning, hop back into your hire car and continue south to your next destination: a beautiful hotel nestled between a historic town and a picturesque marina. You’ll the hug the coast for the entire three-hour journey, making it possible to break up the drive with some scenic stops. One of our favourite spots is Newport, a charming fishing town home to colonies of sea lions and Yaquina Bay lighthouse, the states last-standing wooden lighthouse. After settling into your hotel, head out and spend the rest of today soaking in the vast and varied scenic delights of southern Oregon. The region is known for its spectacular beaches and wildlife-rich rivers, such as the elk of the Elk Preserve. It is also worth visiting the nearby town of Bandon, which specialises in crab fishing.

Today you’ll be bidding farewell to the coast, heading three hours inland to Grants Pass, a small western town nestled in the wild surroundings of Rogue River. Everything here is geared towards outdoor activities, with hiking, fly fishing, kayaking or boat trips all served on a silver platter. If a visit to the famous Redwood National Park is on your USA bucket list, then you could also switch up your route to make a detour to this splendid natural wonder in northern California. On arrival in Grants Pass, check in for the night in a riverside wooden lodge and spend the rest of today enjoying life in the lap of nature. This afternoon we’ve arranged for you to head out on a rafting trip on Rogue River for the opportunity to admire the beauty of the steep cliffs and canyons, as well as the varied wildlife, which includes bald eagles. This evening we recommend enjoying the many delightful markets and eateries that fill the town centre, before heading back to the hotel for a good night’s rest.

Your road trip through the landscapes of Oregon continues today with an hour-and-a-half drive to Prospect, a small town located near the southern entrance of Crater Lake National Park. The journey there is seriously scenic, passing through vineyards, forests, rivers and an increasingly mountainous landscape. Your home for the night in Prospect is a small historic inn in a lovely natural setting, surrounded by forests and mountains. After settling in and freshening up, head out to make the most of the outdoor activities available here, which include jet boating, whitewater rafting, fishing and wildlife watching.

Your next destination in Oregon’s beautiful interior is the small town of Bend, a paradise for outdoorsy adventurers, just a two-and-a-half-hour drive from Prospect. Not long after setting off, you’ll reach the serene and very surreal Crater Lake National Park, a collapsed volcano filled with intense electric blue water that is well worth making a stop at. From here, continue on to Bend and to your next accommodation: a small and comfortable hotel in the heart of town. The rest of today and tomorrow is dedicated to getting outdoors and enjoying the scenic delights of your new surroundings. You can go rafting on Deschutes River, horse riding, cycling and hiking in Smith Rock State Park, whose lunar landscapes are reminiscent of Utah. We’ve also arranged for you to head out for a canoeing adventure on Cascades Lakes, a region known and adored for its peaceful crystal-clear waters and spectacular views of the Three Sisters and Mount Bachelor.

After a hearty breakfast this morning, hop back into your hire car and hit the road northeast through central Oregon to a small family ranch near the town of Fossil, a two-hour drive from Bend. Along the way you can make a stop at John Day Fossil Beds National Monument, a fascinating palaeontology site home to hundreds of fossils. From here the road continues into the beautiful landscapes that surround the Painted Hills, geologically impressive hills that look as though they’ve been painted in charming ochre colours. Once you’ve settled into the friendly family ranch, spend this afternoon horse riding around the grounds in the company of the ranch owners.

The following day is yours to spend here at leisure. You can kick back and relax in the beautiful natural surroundings of the ranch or step into the shoes of a palaeontologist and head out for an archaeological dig in Fossil, the only town in the country where it’s possible to do so.

Today you’ll bidding a warm farewell to your lovely hosts at the ranch and continuing your journey through the rivers, mountains, forests and lakes of northern Oregon to the scenic city of Hood River, a three-hour drive from Fossil. This is a great opportunity to drive along a slice of the legendary Historic Columbia River Highway, a 75-mile highway that hugs the Columbia River Gorge from The Dalles to Troutdale. At times, the river is so vast and the mountains so dramatic that the landscape is more reminiscent of a fjord than a simple river. Your home for the night in Hood River is a historic and characterful hotel well-located for exploring the city for the rest of today. We recommend taking this afternoon to head out on little steam train to Mount Hood (the highest point in Oregon), where you can enjoy a gentle, picturesque stroll along forested trails.

After a hearty breakfast this morning, hop back into your hire car and join the scenic US30 road back to Portland, an hour’s drive through beautiful vineyards and plantations. Along the way you can make a stop in Cascade Locks, a small town home to the historic Bonneville Dam. The town is also a hot-spot for salmon fishing, which you can experience with a paddle boat ride on the river. Check in for one final night in an elegant and comfortable motel and spend the rest of today soaking in the delights of the city and visiting any sights you missed at the start.