Weekend Getaway to Portland

Is the Pacific Northwest calling your name? If you’re a fan of hiking, craft beer, vineyards, and a wide array of food, a weekend getaway to Portland could be a great addition to your travel bucket list. 

Bethany and I have wanted to explore Portland for awhile, so we pick a weekend to get introduced to the city.

Weekend Getaway to Portland

weekend getaway to portland

3 days, 2 nights

  • Day 1 – Travel day to Portland – Grab dinner and explore downtown Portland
  • Day 2 – Pittock Mansion, Portland Farmers Market, Shopping in Pearl District
  • Day 3 – Multnomah Falls / Colombia River Gorge, Willamette Valley vineyards, International Rose Test Garden

If you have extra time:

  • Willamette Valley has over 300 vineyards! Consider spending a full day or two tasting wines and bringing home a few of your favorite bottles.
  • Mount Hood and the Oregon Pacific Coast both make excellent day trips from Portland. You can visit either by arranging a tour or renting a car. In addition, there’s plenty more hiking trails in the area to explore!

Hiking Colombia River Gorge in Portland

Day 1

We didn’t take any time off work for this trip so traveled to Portland in the evening after work. We spent the night grabbing a quick bite to eat at one of Portland’s many food carts (there are over 500!!) and headed over to Deschutes Brewery for some beers.

We stayed downtown at The Westin Portland. The location was perfect. We were within walking distance or a cheap Uber ride away from almost everything we wanted to see.

Day 2

We got an early start to our second day, departing from our hotel on a trail run to Forest Park. We thought the park was only a short three miles from our hotel, but the sidewalk ended on a busy road halfway there. We diverted our route to some residential streets in the hillside neighborhood leading to Pittock Mansion. The route ran up some very steep residential streets, but we enjoyed looking at the beautiful homes built into the hill. When we arrived at the top, we took in the view of Portland before turning back for our hotel.

Pittock Mansion Portland

Pittock Mansion Garden

Next, we headed for the Portland Farmers Market and grabbed some food while lounging, listening to live music and doing some people watching.

Portland Farmers Market

Afterwards, we decided to spend the afternoon checking out 10 Barrel Brewing and some of the unique shops in the Pearl District. After a brief rest at our hotel, we grabbed a beer at Base Camp Brewing before our dinner reservations at Olympia Provisions. Our favorite brewery of the trip was Base Camp. They have a great outdoor patio with live music. We also got a tip from a local (after we had already left, unfortunately) to look up! The ceiling is covered with small lights that look like stars. 

Day 3

The next morning we grabbed a rental car and headed to the Colombia River Gorge for a morning hike. We stopped off at Waffle Window for a to-go breakfast on the way (side note: their waffles are delicious, but nearly impossible to eat while driving).

Waffle Window

Arriving at Colombia River Gorge early was a good decision, as parking was already scarce by the time we arrived. We had a planned 5 mile hike which started at Multnomah Falls, which is worth seeing on its own. Our hike took us from the falls, over a bridge, and to a small observation point at the apex.

We continued on through an epic hike with several more waterfalls and great scenery, making a full loop back to the parking lot. In total it took us about 2 1/2 hours, but we were hustling. I would recommend giving yourself 3-4 hours (plus drive time) to really enjoy it. After the hike we headed back downtown to shower, grab lunch, and head to Willamette Valley for wine tasting.

Colombia River Gorge and Multnomah Falls in Portland

Our first stop was Anderson Family Vineyard, a beautiful family-owned operation situated at the top of a hill. Anderson only schedules private (free!) wine tastings, offering a great way to get introduced to Oregon wine. We also liked the structure of the tasting. We were able to sample several different vintages of the same wine to taste the differences due to that year’s weather. After picking our favorite, we were on our way to the next tasting.

The second vineyard we checked out was Winters Hill Vineyard, located a short drive from Anderson’s. We sampled several wines and picked up a couple more bottles to add to our collection. We were only able to make it to two wineries on our trip, but I wouldn’t recommend more than 3 or 4 in a day (especially if you intend to drive yourself). 

Willamette Valley Vineyard

Satisfied with our new collection of wine, we headed back towards Portland for a stop at the International Rose Test Garden. The park is located near downtown Portland and is accessible with or without a car. It’s is a unique site and a great way to see one of Portland’s most popular attractions (free admission!). We spent almost two hours looking at different roses and just relaxing before heading to dinner.

Portland International Rose Test Garden Collage

For our last meal in Portland we wanted to try Pok Pok but knew the wait could be brutal. When we arrived, we were amazed to discover the wait for two was only 15 minutes! The food was great, but I’m not sure that it’s worth waiting an hour or more on busy nights.

Pok Pok Portland

After dinner, we walked across the street to Salt & Straw for dessert before heading for the airport to catch our late flight home. We polished off a freshly-made waffle cone with a scoop of Fresh Cheese & Strawberries and Freckled Woodblock Chocolate. We spent 20-30 minutes in line, but it was some of the best ice cream we’ve ever had! (And Bethany loves her ice cream). 

We couldn’t have been happier with our weekend getaway to Portland and are excited to explore more of the Pacific Northwest! Do you have any favorite places in Portland? Anything we should see on our next trip?

4 thoughts on “Weekend Getaway to Portland

  1. Love the farmers market photos! Lately I’ve found that’s my favorite thing to do when visiting places. Guess I need to plan a trip to Portland soon!

    • Way late to respond but thanks Tara! 🙂 Portland also has an arts and craft market called the Portland Saturday Market. We didn’t have a change to check it out, but I’ve heard its good as well!

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