One of the tricks of the travel world is to find a destination that offers you the chance to have two (or more) distinct travel experiences with the purchase of one plane ticket.

This is an especially useful and fruitful strategy for people with sparse vacation time or limited budgets, because you can get the most out of your time and money.

There are many places around the world that offer such an opportunity, but a special one resides in the mountain-metro experience you can have in Oregon.

The destinations of Portland and Hood River are separated by just 60 miles, and couldn’t be more different from one another. Each presents unique and complementary experiences that, together, make for a well-rounded trip.

Portland encompasses the creative, artistic culture of Oregon—including a surprisingly great food scene—while outdoor opportunities are found in nearby Hood River, where you can hike, swim, wine taste, and take farm tours.

How to Plan the Trip to Portland and Hood River

The most important thing about planning a double-destination trip is the order in which you visit.

I find that it’s always best to start with the most populated area. In this case, start with Portland and explore its city streets, then head out to Hood River to enjoy more space and scenery.

If you do it the other way around, the sudden burst of density and population could be a shock as you leave a serene environment and pop into a busy city.

Fly into Portland (PDX), then take a ride share, cab, or public transit to your hotel. Explore the city using the same, and rent a car the morning you plan to head out to Hood River.

Use a company with both a downtown and airport location—such as Enterprise—to make things efficient. Rent the car from the downtown location and arrange to return it to the airport on the day you fly out.

Where to Stay in Portland

There are many home bases to be had in Portland, and your familiarity with the city may influence where you want to be. Perhaps you’ve been before and want to check out another part, or have points with a certain chain hotel.

Those situational differences aside, one idea is to stay across the river from downtown Portland in a local neighborhood along East Burnside Street.

Things are a little more relaxed on this side of the bridge, with its own string of local bars, cafes, and restaurants, but you are still within walking distance of its busier, notable neighborhoods, like Old Town and the Pearl District.

In fact, staying in this area leads one to have a rather cool experience: To enter Portland’s downtown and historic area, you can walk across the Burnside Bridge, which provides beautiful views of the city skyline and the Willamette River. This on-foot entrance is a rather epic gateway and a picturesque perspective on the city.

If this area intrigues you, check out the Jupiter Hotel, which is really two hotels in one. Located across the street from one another, the Jupiter Original has simple but artistic rooms (think big murals with a 3-star retro vibe) with a low-lying, apartment-style building layout, while the Jupiter NEXT is more modern, a bit more upscale, and is a taller building, offering views of the Portland skyline.

What to Do in Portland

Like most cities, Portland is a very diverse place, with many neighborhoods to explore. Don’t miss the Pearl District, Nob Hill, or Mississippi Street, to name a few.

There are many platforms upon which you could explore the city—art, music, beer—but it may surprise you to learn that Portland’s best kept secret is its food scene.

Despite being ranked many times as one of the best food cities in America, it’s certainly not the first place that comes to mind for most people (feel free to conduct your own polls with your friends).

Last spring, Portland was ranked as the #10 best food city in the world by Time Out Magazine; a 2022 survey by WalletHub called it the best food city in the county, as did the Washington Post all the way back in 2015. The city’s food truck and vegan scenes were also highlighted and awarded in recent years, as was its pizza scene (much to the dismay of New Yorkers).

For whatever reason, these accolades have not penetrated the mainstream thinking. But eating and drinking in Portland is certainly the thing to do, especially in our scenario here, where fueling up for the active adventures to come in Hood River is priority number one.

To plan out your food journey in Portland, head over to Eater Portland, where you will find the latest buzz on the city’s food scene, including new, trending, and yet-to-be discovered restaurants. Its maps can help you find any kind of food you may be looking for in different neighborhoods (such as pizza).

If you’re not sure where to start, check out the 38 most essential restaurants in Portland.

To warm up your legs for the outdoor adventures to come in Hood River, head up to Portland’s Washington Park. Here you will find endless green space for picnicking, as well as some lovely scenic spots: the International Rose Test Garden, a Japanese garden, and a variety of other attractions that provide great views of the city below and Mt. Hood off in the distance.

What to Do and Where to Stay in Hood River

Hop in your rental car and as you drive east from Portland, you will enter the Columbia River Gorge National Scenic Area, a protected area spanning 80 miles along the Columbia River on the border of Oregon and Washington.

Long before you reach the town of Hood River, you’ll find yourself in a completely different world. Beautiful blue waters, craggy cliffs, tall spires, and pine-covered mountain ridges replace skyscrapers and the city skyline.

Your travels will parallel the Columbia River, with views that may entice you to roll down the windows on a nice day. You’ll be in Hood River in about an hour—unless, of course, you are drawn to drive slower and stop off on the scenic viewpoints along the way, which include Shepperd’s Dell Falls, Bridal Veil Falls, and a variety of state-run parks.

Hood River is a hub of recreation in the Columbia River Gorge and a launching point for adventures in the nearby Cascade Mountain Range, including Mt. Hood and the surrounding fruit and wine byway.

In town, you’ll find a variety of small lodging options, including the historic Hood River Hotel. Those looking for old-school style lodging with character should look no further; here, you will be given a real key to your room, with vintage-style furniture, historic photos, and local artwork setting the rustic vibe.

The downstairs restaurant, Broder Ost, brilliantly puts modern twists on traditional Scandinavian comfort food, evoking the old-time feel of a mountain meal while sourcing from local farms.

It’s a nice place to fuel up before heading out for a day of adventure, which can include hiking, biking, watersports, skiing, wine tasting, or farm tours, depending on the time of year.

Here’s a rundown of the main recreation areas:

  • Fruit and Wine: The Fruit Loop is a 35-mile scenic journey that travels through local orchards, forests, and farmlands. Fruit and wine are the main draw, but you can also find other opportunities, like lavender and alpaca farms. Check out this database of local farms to find individual and unique experiences.
  • Mt. Hood National Forest: There are many local trails around Hood River, but one would be remiss not to drive a little farther and pay a visit to Mt. Hood National Forest. Here you can find myriad hiking and biking trails, as well as skiing in winter (Mt. Hood Meadows Ski Resort).
  • Columbia River: Hood River sits adjacent to the Columbia River, where you can do a variety of outdoor activities, including paddling, windsurfing, sailing, or swimming. If not familiar with the river’s conditions, I strongly recommend going through a local outfitter to have the best experience. Cool off after a hike with a swim at the local beach park.
  • Other Nearby Small Towns: To get a better sense of local life outside of busy Hood River, cross the Columbia River into Washington State and check out White Salmon, or head upriver on the Oregon side to Dallesport. This map of the Columbia River Gorge National Scenic Area is helpful to see all the nearby towns.

The recommended length of stay in Hood River is at least two or three full days in order to be able to experience a little bit of everything it has to offer. Of course, you could certainly stay longer—there is much to do.

When ready, enjoy the last of the views as you make the easy one-hour drive and cruise back to Portland for your flight out of PDX. Simply return your rental car to the airport to complete the loop, and reflect back on all you’ve seen in a short time—one trip, two destinations.



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