Lady’s Three Days in Portland, Oregon Guide

Today I want to share my guide to spending three days in Portland, Oregon with you. This city in the Pacific Northwest of the United States is a great place to eat, drink, and channel your inner hipster.

Three Days in Portland, Oregon

After an epic road trip along the Oregon coast, I’m heading inland to explore more of the state’s highlights.

Specifically, I’m driving east to Portland, the darling of America’s hipster scene and one of the hottest travel destinations in the US right now.

I’m going there not only to experience the city’s food scene, but also the surrounding area’s wine and waterfalls. And when I arrive, my three days in Portland go something like this…

Portland, Oregon

Oregon’s most famous city, Portland is a food mecca and a magnet for those seeking to start over in a new state and a new state of mind.

Down-to-earth to the point that it’s hard to find a shop open on a Wednesday afternoon (lots of “brb” and “out to lunch” signs downtown), and environmentally conscious to the extent that Powell’s, the city’s famous bookstore, features titles that encourage customers to raise their own chickens, it’s hard not to chill out as soon as I arrive.

And I do just that. After checking into a hip room at the Kimpton Hotel Vintage Portland, I start my three days in Portland by exploring the downtown area.

The buildings are all low-rise, making it feel approachable, and the people are as friendly and open as any on the West Coast. There’s street food and street art everywhere I look, and the shops and restaurants are warm and welcoming.

But while Portland’s restaurants are amazing—I have great meals at Ava Gene’s, Oven and Shaker, and Lardo—it’s the city’s food carts that really set it apart as a culinary capital.

Food Cart Tour of Portland

I learn this on a food cart tour of Portland with Brett Burmeister, owner of Food Carts Portland. He takes me around to some of the city’s best during my three days in Portland.

Grazing while learning, I visit the most concentrated food cart area in America at the Alder Pod, “pod” being the name for food cart clusters throughout the city.

While there, I also learn that the downtown food carts and the Eastside food carts differ in that the former all face out onto the street and cater to those taking food away, while the latter face in and cater to those wanting to sit and eat.

Either way, I learn that the food is both international in scope—there’s everything from Hawaiian to Egyptian in one pod—and high in quality and taste.

Willamette Valley

But the city doesn’t have a monopoly on Oregon’s eating and drinking scene, and it’s worth doing a day trip to the Willamette Valley during my three days in Portland to explore the state’s most famous beverage: wine.

An hour’s drive from the city, this wine country produces some of the best Pinot Noir in the US—if not the world.

Thanks to Travel Oregon, which has arranged my trip to Portland, I have a chance to visit the Willamette Valley with Ken Wright from Ken Wright Cellars.

An industry heavyweight, Ken has been on the cover of Wine Spectator magazine and knows more about this region than I ever imagined.

As he drives me through the vineyards, he tells me all about the area and its Pinot Noir before we return to the winery in the pretty town of Carlton for a tasting.

Also in town is the Carlton Winemakers Studio, an incubator where fourteen winemakers share space and produce new and often innovative wines.

I stop in for a tasting, sampling a range of wines and getting a behind-the-scenes tour where I discover there’s a climbing wall behind the barrels. Only in Oregon!

Columbia River Gorge

But the Willamette Valley isn’t the only wine tasting day trip from the city, and there’s enough time to do another during my three days in Portland.

Out in the Columbia River Gorge, wineries like Wy’East Vineyards and Cathedral Ridge Winery are great places for wine tasting with a view.

They’re also close to some of Oregon’s famous waterfalls, and on a day trip with EverGreen Escapes I get to visit both the wineries and famous falls like Starvation Creek, Latourell Falls, and the mighty Multnomah Falls.

Wine Tasting in Portland

Back in Portland, I conclude my trip with more wine tasting at one of the city’s urban wineries. A new trend, they’re bringing the winemaking process closer to home with cellar doors in city centers.

I visit the Southeast Wine Collective, where I try great wines from a number of different local winemakers.

Three Days in Portland and Beyond

And after three days in Portland, it’s time to stop sipping and start traveling on. But I can’t bring myself to leave the Pacific Northwest just yet.

I hop on a train to Seattle, enjoying spectacular views of Oregon’s lakes and mountains as I travel north to Washington. To be continued…

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