Traveling to Portland, Oregon for the first time? With so much to do, see, and eat, narrowing down your list can be tricky. Here’s my list of tips for Visiting Portland, including restaurants, bars, hotel, and more.

My husband and I stayed in Portland for four nights in April 2018. First we spent a weekend along the coast, driving from Cannon Beach to Florence. Check out everything we saw on our road trip in my post, here. Then we settled down in Portland for the next five days. We took two day trips during our stay: chasing waterfalls along the Columbia River Gorge and hiking the trails on Mount Hood. The remaining two days were devoted to Portland! Here’s what we managed to do, see, and eat during our short stay.

Where to Eat & Drink

(1) Multnomah Whiskey Library

Address: 1124 SW Alder St, Portland, OR 97205
Hours: 4 pm -12 am Mon.-Thurs., open until 1 am Fri.-Sat.; closed Sundays
Website: https://mwlpdx.com/

If you aren’t paying attention, you may walk straight past the entrance to this very cool whiskey bar. It was by far our favorite place we visited in Portland. Fair warning, its not a wallet friendly bar, but if you love whiskey and old world charm, add this to your list of places to grab a drink! Besides, you can don’t have to choose a top-shelf whiskey. Plus, they serve more than just whiskey!

I highly suggest visiting the Library during the winter because the decor is that cozy! There is a fireplace and leather couches that would be so inviting during colder weather. I’m not sure how you get to snag a spot in one of the seating areas, though, since we were directed straight to the bar. Maybe if we were a larger party. But, a plus to sitting at the bar is the amount of help you get from the staff in picking out and tasting different whiskeys.

There’s also a more casual bar downstairs known as the Green Room, aptly named for its decor.

(2) Deschutes Brewery

Address: 210 NW 11th Ave, Portland, OR 97209
Hours: 11 am – 11 pm; open until 12 am on Friday and Saturday
Website: https://www.deschutesbrewery.com/

During our stay in Portland we knew we had to make time to try some coffee and beer! There’s a big craft brewery scene in Oregon. Deschutes is an Oregon beer company that has been around for 30 years and located in Bend, Oregon. The company has several restaurant locations across the state. Only a 5 minute walk from Powell’s City of Books, Deschutes Brewery is a great place to stop for dinner after browsing the aisles of the famous bookstore. The beer was very good, especially the St. Patrick’s beer they were still offering in April!

(3) Cheryl’s on 12th

Address: 1135 SW Washington St, Portland, OR 97205
Hours: Sun-Tues. 7am – 4 pm; Wed.-Sat. 7 am – 8 pm (Note: opens at 8 am on Sat. and Sun.)
Website: http://www.cherylson12th.com/

Who doesn’t like a restaurant that serves breakfast late? I love being able to sleep in, even on vacation, and know that I can still get french toast and coffee. Cheryl’s on 12th serves them until 4 pm! My kind of restaurant. Also, as you wait for your food, you get a free sampling of their version of beinegts. Since we love eating big breakfasts when traveling so we can skip a meal (saves money and allows us to spend more time sight seeing), we returned to Cheryl’s more than once for a hearty breakfast.

(4) Blue Star Donuts

Address: 1237 SW Washington St, Portland, OR 97205
Hours: 7 am – 8 pm
Website: http://www.bluestardonuts.com/

The famous Voodoo Donuts was on the other side of town from where we were staying so we never tried a Voodoo Donut. Blue Star Donuts, however, was close by and still open when we were craving dessert. I’ll be honest, I prefer smaller, fluffy donuts like you get from Shipley’s Donuts, but it was okay considering the place was about to close down for the day.

(5) Pine Street Market for Ramen, Ice Cream, and More

Address: 126 SW 2nd Ave, Portland, OR 97204
Hours: 8 am – 11 pm, but depends on the restaurant
Market website: http://www.pinestreetpdx.com/

Wiz Bang Bar website: https://saltandstraw.com/wizbangbar/

After exploring some restaurants and bars on the other side of the river, we were craving something light for dessert. With everything closing fairly early in Portland, we thought we would be out of luck. But we found the Wiz Bang Bar! This soft-served ice cream was popular and worth the wait. The line never died down while we were there. The market place offered several varieties of food, from Ramen to Burgers. The decor makes you feel like you’re in New York, not Oregon, too. I suggest visiting this place for a quick, cheap bite to eat!

There is a Blue and Red MAX Line located within walking distance at Oak Street and SW 1st Ave Eastbound.

(6) Departure Restaurant & Rooftop Lounge

Address: 525 SW Morrison St, Portland, OR 97204 (Top Floor of The Nines hotel)
Hours: 4 pm – 11 pm; open until 12 am on Friday and Saturday
Website: http://departureportland.com/

This bar is conveniently located at Pioneer Courthouse Square. When entering the hotel lobby, there is an elevator specifically for Departure. Exiting the elevator was a little disorienting as the doors open up to a dark hallway leaving you nowhere to go but to the left. We took another left down another dark hallway. It felt like we entered a night club and we immediately thought we were under dressed. But once we entered the bright light of the afternoon sun we were reassured that we fit in. As swanky as the bar looked, it was a very relaxed atmosphere. People’s attire ranged from very casual to cocktail dresses.

During our stay in Portland we were blessed with sunny skies every day. This means that it was extremely sunny and hot on that rooftop. On an average Portland day it probably feels very comfortable. Just in case, I recommend bringing sunglasses and a hat for happy hour if the sun is out! We were lucky enough to find one of the few seats in the shade (after some maneuvering).

If you’re looking for great views of the city, this is the place to go!

(7) Food Trucks

There are a lot of Food Trucks in Portland. We didn’t stop at any during our visit, but if you’re interested, click here for a list of the “Food Truck Pods” in Portland. The largest pod we saw was on SW 10th and Alder Street.

Where to Stay: Hotel Deluxe

Address: 729 SW 15th Ave, Portland, OR 97205
Website: https://www.hoteldeluxeportland.com/

Designed in the “Hollywood Glory Days” style, this hotel invites its guests to experience Old Hollywood glamour from dawn to dusk. Each floor has its own theme and rooms have their own unique artwork devoted to a certain actor. The radio, pictured above, actually works and was set to classical music when we entered. Nice touch.

The art deco style is most notably on display in the hotel lobby. Images from class films and famous actors are featured center stage. When passing through the lobby in the morning, be sure to grab a free coffee to go! It’s actually very good.

It’s location may seem far from downtown, but its only a short walk over the highway. But, if you don’t feel like walking, there is a MAX Line station two blocks away at Providence Park. If you’re driving into Portland, consider looking for alternative parking. The parking garage across the street is around $30 a night, and valet is a few dollars extra. We parked at the Smart Park garage on 730 SW 10th Ave instead. (Bring your ticket with you and pay before returning to your car).

Gracie’s & the Driftwood Room

You will feel like you’ve stepped back in time when dining at Gracie’s or having a cocktail at the Driftwood Room. The furniture, lighting, and music is exactly what you’d see in an Old Hollywood movie. We ate breakfast at Gracie’s on the mornings we took day trips to Columbia River Gorge and Mt. Hood because it was our quickest option. The other incentive was the coupons we received every night for dining at the hotel’s restaurant. Best part about the Driftwood Room? It stays open until 11:30 pm on weekdays and 12:30 am on Friday and Saturdays. In a city that seemed to go to sleep early, this may be one of the few places open late.

What to Know for First Timers

(1) Public Transportation

Portland’s public transportation system is one of the best that I’ve experienced in the States. Getting around the city was extremely easy. With the exceptions of the Pittock Mansion and our day trips, we were able to move around the city without needing a car. With several metro lines, bike lanes, and an aeiral tram, you’ll have no problem navigating the city.

♦Tri Met is the company that runs the buses, light rail, and commuter rail. The main mode of transportation is the MAX Rail System. Here’s how to ride:

1. Visit the Tri Met website to look up stations and lines. Or download the Hop Fastpass App.
2. Purchase tickets before boarding. Hop Fast Pass Ticket machines are located at stations. Once you buy your ticket, check to see if there is an additional machine for validating your ticket. It may come pre-validated.
   1. 2 1/2 hour fare = $2.50
   2. Day pass fare = $5
3. Keep your ticket on you in case there is an inspector.
4. If its your first time using a Light Rail System and are nervous, check out this video.

♦ Portland is a bike friendly city. Bike lanes are clearly marked with bright green paint in many areas across the city. The Bike Share Program in Portland is Biketown. To learn more about cycling around the city, check out Biketown’s website.

♦ The Aerial Tram is used mostly by commuters, but if you want to spend $5 to see a view of the city, river, and three mountains on a clear day, ride the tram! Ticket kiosks are located at the lower terminal and accept debit/credit cards only. The upper terminal leads to the medical district, so take a right turn as you enter the building to walk along the terrace. See more (including 2018 closure dates) at the Go By Tram website: http://www.gobytram.com/

(2) Driving in Portland

There are a few things you should know if you’re driving during your stay in Portland. First, parking is expensive! Do some research ahead of time to find the cheapest parking available near your hotel. See above for what we did while staying at the Hotel Deluxe. Second, there are no gas stations in the city despite what Google Maps says. (If you know of one, share in the comments!) Be sure to fill up your gas tank before reentering the city if you’re taking day trips. Third, if you plan on refilling your gas tank before returning to the airport, there is a Shell and 7-11 nearby, off of highway 205. Lastly, if you’re used to driving fast you may be disappointed with driving in Oregon. We never saw a speed limit over 55 mph.

(3) Homeless Population

This is a sensitive subject, but I feel its worth noting. There is a high population of homeless people in Portland. It’s hard not to notice or ignore.

If it makes you uncomfortable (and it does for some), avoid traveling around the city after 9 pm. The city streets are pretty empty after sundown except for those who have nowhere else to go, so you’ll be very aware of the problem Portland is facing (i.e., housing shortage, poverty levels, shelter needs, etc.).

If you want to learn more about Portland’s situation and how to help its citizens, check out Travel Portland’s website, here.

Portland is a beautiful city and it should be enjoyed by all. Be courteous and conscientious, but also safe.

Have you been to Portland? What are some of your places to eat and stay? Share your tips in the comments!

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