Oregon Road Trip: Portland and Greater Portland Region

In October 2017 John and I took a road trip across Oregon (our fourth!). We spent a week traveling throughout Portland, the coast, southern Oregon, the Willamette Valley, and central Oregon. These trip recap posts will be organized by region for guidance, in case you want to replicate anything we did on our trip. The map reflects the days traveled, and I will reference what day the pictures/information corresponds to.

OR Map 1

Portland is absolutely one of my favorite cities in the world. We often daydream about what it would be like to live there, but for now we’ll just keep visiting. One of the best things about being a repeat visitor is that you discover favorite local spots that you can go back to every time you’re in town, just like you would at home. You’ll notice that several of the spots on this road trip were repeats for us – hopefully that’s not boring to you, the reader, but rather a ringing endorsement of a location that is absolutely worth visiting; if we’re going back, it’s something we really love.

Let’s get started in Portland proper.

Lunchtime on Day 1 brought us to a place we’ve wanted to try out for a while: Pok Pok on SE Division. They are doing authentic thai/vietnamese cuisine that was incredible. Unreal flavors, perfectly balanced spice, super tender meat (ribs and chicken skewers were equally delicious). The ambiance is really funky and cool too.


After lunch we walked around the Richmond neighborhood and did some shopping. PDX has the coolest shops – they’re funky and eclectic, and remind me of what we have at home in Somerville.



Day 1 also brought us to Laurelhurst Park. I’d had this on our bookmarked to-do list for a while but somehow we hadn’t made it there yet. One thing I want to impart is that, yes, the Pacific Northwest is rainy much of the time but the great thing is the rain doesn’t linger long so walking around outside or going to park is still something you can totally do on a regular day. You just need to find the right window of time.


Laurelhurst Park was bigger than I thought it would be and was a perfect 15-20 minute walk around.


Much like all of the parks in PDX, Laurelhurst is a perfect, green oasis that is peaceful and pleasing to the senses.



As you know, we very much have drank the Voodoo Doughnut koolaid but we decided to try out Blue Star Donuts on this trip. We went to the Hawthorne neighborhood location and I had the buttermilk old fashioned. It was good. I am a simple donut fan – if you’re not doing the classics right, you’re failing. And I think both Voodoo and Blue Star are doing the classics right, even if they are known for their funkier flavors.


Another new park we visited was Cathedral Park.



The site is believed to be one of the 14 Lewis and Clark landing sites in the Vancouver-Portland area. In 1931, the St. Johns Bridge was built on the site; it is the only steel suspension bridge in Portland. The park got its name from the bridge’s beautiful cathedral-like arches.


On Day 7, when we boomeranged back into PDX, we made a point to have lunch at our favorite spot: The Observatory. A trip to Portland wouldn’t be complete without getting the cheese plate from The Observatory. This was our third visit here and I wouldn’t miss it for the world.


Day 7 also brought us back to Voodoo Doughnut (the Voodoo Doughnut Too location, which is our favorite one). A delicious, decadent treat for sure. Because Portland is such a donut-heavy city, I recommend trying as many donuts as you can stand and figuring out which your personal favorite is. The peanut gallery is pretty divided on this topic, I’ve found!



In terms of hotels we usually splurge in PDX and stay at the Heathman Hotel. We stayed here for our honeymoon and have been back three times since. It’s a beautiful, luxurious hotel in a great location downtown. It’s spendy, but worth it.



Just around the corner from the Heathman is one of the Portland Farmer’s Market locations (Pioneer Courthouse Square).


The market is great – we’ve been to several of the other locations. The produce is extremely fresh, the flowers are stunning, the vendors are diverse, and the food is all delicious. I think this location is my favorite!



A trip to PDX wouldn’t be complete without visiting Powell’s Books. It’ the best book store I’ve ever been to. Even if you’re not in the market for a book, you could still spend hours in here. Their collection is vast and the set up inside is impressively organized.


One of our favorite neighborhoods in PDX is Arlington Heights in southwest Portland. It’s full of gorgeous homes and lush parks. One of those parks, a must-visit, is the International Rose Test Garden.







Arlington Heights is adjacent to Forest Park, one of the largest urban forest reserves in the US. It connects over 70 miles of trails, though our afternoon walk on Day 7 was about 30 minutes. It’s the perfect spot for any length you want to go for.


Two snack/afternoon treat recommendations for Portland proper are Salt & Straw ice cream – any location is great but we prefer the Alphabet District shop. You absolutely have to get the ice cream flight so you can sample four different flavors. The second is Tea Chai Te – also in the Alphabet District, though there are a few other locations.  It’s a great place to grab a tea (they have 120 different tea selections!), sit, and unwind for a bit. Plus the neighborhood is full of cute shops and fun window shopping.


One final recommendation for Portland that was new to us was Nostrana in the Buckman neighborhood. Their specialty is wood-fired pizza and pasta – basically rustic Italian – and they did not disappoint. We had dinner here on Day 7 and it was the perfect meal to end the trip. The ambiance here is very cool too, there’s a vaulted ceiling with rustic beams and a big wide open kitchen.


Bye for now, PDX – on to the greater Portland-area!


For the remainder of this post I’m including several greater-Portland area spots we visited. I consider this area to cover spots within an hour’s drive of Portland that are worth visiting or may strike your fancy.

St. Helens, Oregon is roughly 45  minutes due north of Portland, up the Columbia River. It was founded in 1845. Now it’s a quiet town and is most notably the home to many films, such as the Disney Channel’s Halloweentown and Twilight. Because it was October we stopped in on our way through to see the Halloweentown set up. It was cute and basically empty. Not a must-see, but a fun and festive Fall pit stop.


Forest Grove, Oregon is about 45 minutes west of Portland and is home to the McMenamins Grand Lodge. I can’t recommend staying here enough! It’s the perfect overnight if you’re headed out of town or back into town.


If you aren’t familiar, McMenamins is a chain of hotels, breweries, historical sites, event spaces, venues, etc. Their properties are extremely unique and the Grand Lodge was no different.


The Grand Lodge opened in 1922 as a home for former Masons and their families. It served as a 72-unit community for them until 2000 when it opened as the Grand Lodge. We stayed in the Helen & Tom Stevens room.


The Grand Lodge now has 90 guest rooms and the following amazing features within the property:

Restaurants, lounges and meeting spaces.


Outdoor cafe.


Huge grounds, several restaurants.


Separate wings with different room types, Ruby’s Spa.


Doctor’s Office bar, sitting rooms.


We had dinner at the Ironworks Grill and it was very good. It’s so convenient and cool to have everything you could possibly need all on site. You never need to leave!


Oregon City, Oregon is 30 minutes due south of Portland. We drove through on Day 7 on our way back into town and we stopped briefly at the End of the Oregon Trail Historic Site. They were closed so we didn’t go into the Interpretive Center but I wish we could have checked it out. The outside was cool!


My favorite greater-Portland area attraction is the Bob’s Red Mill Factory and Flagship Store in Milwaukie, Oregon, about 15 minutes south of Portland.



This location is the world headquarters and offers factory tours once a day, Monday-Friday. We’ve been to the store before but the timing never lined up to take the tour – until this trip! This was actually the first thing we did on Day 1 so it really kicked our trip off on an awesome note.


Clearly they love Bob – he’s everywhere!



The factory tour was one of the best I’ve been on – there are viewing areas into every space on the factory floor. Our tour guide, Cheryl, was also amazing – she knew every single thing about the company, its history, and products.



Imagine our surprise when Bob Moore – the Bob, founder of Bob’s Red Mill – showed up and joined our tour! He spoke for a bit about the history of company, met with everyone, and took pictures with all of us. He was funny, generous, and full of information. It was an absolute treat to be able to meet him. Like I said, this was the first thing we did on Day 1 of this trip and we haven’t stopped talking about meeting Bob since!



Free samples at the end of the tour!


Next up on our regional tour of Oregon state: The Oregon Coast!

Author: Domestocrat

I'm a lady who enjoys photography, football, cooking, long drives with the windows down, This American Life, kettlecorn, hot yoga, pop punk, my nephews, my cat Reggie, and my home: Boston.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s