Portland Oregon

Oregon | United States

Portland Oregon

Portland is a fun and quirky city with wonderful restaurants, pretty parks, and the best books store in the world. Enjoy a weekend visit, or use it as a launching point for a further exploration of the state.

Length: 2+ days

Transportation: rental car or uber/taxi/train (if no daytrips outside of Portland planned)

Guide Book: Fodors Pacific Northwest, A Falcon Guide: Walking Portland, Oregon

Day 1 – Portland

Day 2 – Portland

Day 3 – Columbia River Gorge

  • Drive to the Columbia River Gorge (30m drive)
  • Crown Point Vista House Lookout
  • Stop at waterfalls along the way (pullouts clearly marked)
  • Drive to Portland
  • Dinner – Select an option not tried the night before
  • Lodging—same place (night 3/5)

Day 4 –Willamette Valley

Day 5 – Cannon Beach

In Depth Itinerary

Day 1 – Portland

Arrive in Portland.

If you plan to do day trips from Portland, you should pick up a rental car at the airport. If you plan to stay in Portland only, you can uber/lyft, cab, or take the Max Lightrail and buses.

Portland is a pleasant city with a walkable downtown, nice neighborhoods, and a relaxed atmosphere.  

To start your day in Portland enjoy a Portland walking tour. Then head to Powell’s City of Books. Powell’s City of Books is the largest independent bookstore in the world. We found it easy to spend a couple of hours here. Look for the little recommendation cards as a suggestion to where to even begin. It’s so big you can grab a map when you walk in. Stop for a coffee at the cafe after if you need a pick-me-up or place to read.

In any case regardless of when you arrive you will need to eat and we suggest an introduction to Northwest wine and food at the Oui! wine bar and restaurant. It is not right downtown but the food is really great and it’s in a nice nearby neighborhood.

After dinner grab ice cream at Portland’s legendary ice cream shop Salt and Straw.

For a hotel that’s downtown with some charm, consider the Ace Hotel or The Society Hotel. These boutique hotels are very enjoyable. You can also consider the Hyatt House Portland / Downtown which is far less interesting but on a convenient streetcar line to downtown and and on a nice park along the river. If you have points you need to burn this may be a good option. Alternatively you stay across the river at a B&B. Our favorite one shut down but the The Lion and the Rose is housed in a pretty Victorian. Lodging is quainter and more residential across the river from downtown and there are good bars and restaurants, however you will have to commute into town for any activity which can be a downside. Also consider Airbnb or an apartment rental given you will be in town for multiple days and can grab groceries/cook to reduce costs.

Day 2 – Portland

Begin at Voodoo Donuts if you want to try this Portland staple. It always has a long line and unless you really enjoy unusual donuts it may not be worth it, but we have to throw it in here. Another very good donut option is Blue Star Donuts. From here head toward the water and check out the charming little Lan Su Chinese Gardens then continue down to the river where on both Saturday and Sunday the Saturday Market has a large craft and food market. From here head back up to Oregon’s famous Dechutes Brewery and Public House for lunch and to sample some of the craft beer that Portland is so famous for. Then head out to the Japanese Gardens and the International Rose Gardens for some gorgeous parkland and flowers very near downtown Portland. You can do all these things by walking or by public transit (Portland has the Max Lightrail and buses), or drive if you’re so inclined.

For dinner there are many options – consider Willow, Kachka or one off our list of recommended restaurants. After dinner consider drinks at Drinks: Hopworks Urban Brewery or Multnomah Whiskey Library

If you are in town on Saturday Portland State University hosts a large Farmers Market with over 100 vendors.

Day 3 – Columbia River Gorge

The beautiful Columbia River Gorge has great scenery and lovely waterfalls east of Portland. Make sure to stop at the many waterfalls and viewpoints clearly marked on the Columbia River Parkway.Here is nicely laid out the stops along the way. Make sure to stop at Multnomah Falls and grab lunch at Multnomah Falls Lodge (reservations suggested). Do the 2 mile Multnomah Falls Trail hike to stretch your legs. Our general recommendation is to start by getting out of the car at Crown Point Vista House Lookout and proceeding, getting out at various waterfalls, until you reach the Multnomah Falls where you can turn around and head back to Portland But really, drive as far as you like.

Day 4 – Willamette Valley

The Willamette Valley has is a cooler environment than Napa in California and the emphasis tends to be Pinot Noir and whites rather then Cabernets and Zinfandels of California. Our absolute favorite combination is visiting Bells Up Winery followed by Vidon. Both are small winemakers, off the beaten path, and very good. At Bells Up you’ll get a personally curated appointment with the winemaker himself. At Vidon you’ll get sweeping views. If you’re still ambitious, consider adding on Utopia Vineyard, Adelsheim, Trisaetum, Alloro, or Penner-Ash. The cute little town of McMinnville is nearby and has some good dining options – look at Ruddick/Wood and Storrs Smokehouse – if you wish (it’s also a nice area for picnicking). Then drive back to Portland for the evening.

View from Penner Ash winery over the Willamette Valley

Day 5 – Cannon Beach

Drive to Cannon Beach and Ecola State Park. Once you reach the water you are in for some beautiful coastal scenery. The Pacific coast is often foggy so have warm clothing available, but the fog also often burns off by afternoon. We suggest a visit to Ecola State Park where you can do the Clatsop Loop Trail or Ecola State Park to Indian Beach Trail hike. Don’t miss a stop at the beach at Cannon Beach (park at lot at South Hawthorne and East Gower and walk along East Gower to beach access). Cannon Beach is huge, beautiful, and offers enormous sea stack. Wander along the beach or have a lazy afternoon to your heart’s content.

Ecola State Park

For a unique dining experience eat at Cannon beach hardware and public house which offers excellent food and drink at a hardware store (yes, you read that right). Or for a pub-like experience, head to Pelican Brewing next door. After you’ve enjoyed the scenery and food, drive back to Portland.

Cannon Beach

If you’re interested in extending your trip, look at our Pacific Coastal Northwest Itinerary.

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