What to do in Portland if You Only Have One Weekend

Things to do in Portland... Portland Travel Guide, A Weekend in the City | itsaLisa.com

You’re on a mission to conquer Portland in one weekend? What a quest! The token “weird” city is brimming with quirks and culinary feats. It would be impossible to see it all, but since you’re here and you’re trying, follow along as I guide you through the town highlights, as well as some of my personal favorites.

How it works: For the purpose of this post, let’s pretend you’ll arrive in Portland Friday night and leave Sunday night. I’m going to describe what my ideal trip would look like in the given time frame. Use THIS GOOGLE MAP that I made just for you along with the written guide below for your ultimate PDX tour.

Guide to PDX | itsaLisa.com

PORTLAND CITY GUIDE: A Weekend Agenda

FRIDAY: South East Portland

You’ve traveled all day and you’re starving! Where to first? Let’s start with food, then drinks. The layer titled “FRIDAY NIGHT. SE PDX” on my Google map will show you where to go. First stop is one of Portland’s hidden delicacies.

Le Bistro Montage, Portland Oregon | itsaLisa.com

Le Bistro Montage 301 SE Morrison St. Dine at this Cajun restaurant famous for their mac and cheese, but feel free to explore their wild seafood menu, you never know when your next chance to try alligator might be. Words of the wise, do not eat it all!!! Ask your waiter if you can take some to go; a surprise awaits. 😉

Now that you’re fed, time for some drinks. That’s the real reason you’re here, right? Let’s keep Friday night a quiet night. You have a big weekend ahead of you.

Rontoms 600 E Burnside St. Grab a drink and head out back to the large open patio and take in the laid back culture. Play ping-pong and mingle with the locals.

Maybe you’ve had a long day and this crowd is enough. Or maybe you’re just getting started and want to see more.  We will stay on the Northeast side tonight, so make your way up E Burnside St and follow along with this bar crawl. That is, if you’re up for it. The bars are going to get even better tomorrow so reserve your energy if needed. The following are all in walking distance from each other…

The Standard 14 NE 22ndPlay corn hole, America’s new favorite game, at The Standard (not to be confused with The Standard Hotel in LA or NYC). Sing Karaoke at the Chopsticks Express. Cheer on the Timbers (Portland’s one and only soccer team) or catch a live show up the street at Beulahland. Hop next door to Red Flag for Pinball and, dare I say, frozen Margaritas. Or mingle with more of your bearded locals at Laurelthirst Public House, did somebody say bluegrass?

Now that was a chill evening. You had a taste of the local nightlife, I think you’re are ready for a good night’s sleep, because tomorrow is jampacked with the touristing best!

SATURDAY: Everything Portland

Rise and shine my friends! Grab your Doc Marten’s and Northface, and get ready to hit the rain-soaked streets. I have divided today into three parts. 1) An introduction to the city, 2) afternoon options for you, and 3) a night out you will never forget.

SATURDAY MORNING: The Tourist Tour

Stumptown Coffee, Portland | itsaLisa.com

Stumptown 128 SW 3rd Ave.  Fuel up with Portland’s finest coffee. “The name, a nod to this beloved city’s historic logging legacy.” –Stumptowncoffee.com. Craft brewing is an art well-known to Oregon. Stumptown was the first.

(Park in this downtown region because I lead you in a full circle so you’ll be back at the car within a few hours.)

Voodoo Doughnuts, Portland | itsaLisa.com

VOODOO Doughnut 22 SW 3rd Ave. While you’re sipping your coffee, head over to the sparkly line at Voodoo Donuts just next door. Checkout their menu here, my favorite is the ODB, your average doughnut covered in chocolate, Oreos AND peanut butter – YUM! With Voodoo and Stumptown in hand, you’re already a true tourist, err, I mean local.

Portland Saturday Market 2 SW Naito Pkwy. Now that you’re fueled with the blood of Portland, walk across the street to Saturday Market. Make sure you meander through the shops all the way to the waterfront. Enjoy the orchestra, the wind chimes, the weirdos, but most importantly, the Spoonman. No trip to Saturday Market is complete without trying on Spoon glasses, or purchasing a decorative-flatware-ring. Before you move on, snap a pic by the waterfront and enjoy the scenic view of Portland’s bridges. If you need to refuel I recommend trying an Elephant Ear or grabbing a bite at one of the snack huts lining the waterfront, but it’s not time for lunch just yet!

Powell’s City of Books 1005 W Burnside St. Next on the list, walk straight up Burnside and find yourself at the doorsteps of the biggest new and used bookstore in the world! *Helpful Hint: go with a purpose, have 1 or 2 books in mind and peruse the color coded aisles ’til your heart’s content.* If you’re not into books, meander across the street and peruse the aisles of trendy second-hand Portlander clothes at Buffalo Exchange while you wait. Woohoo, you’ve finally found the book you’ve been hoping for! All that hunting has made you hungry. Good thing Portland is overflowing with food options.

Portland Food Carts SW Alder St & 9th. For lunch on Saturday, enjoy the open air and stroll over to the biggest pod of food carts in Portland. A pod is a group of food carts that gather together to give you the best variety of food. I like to walk around the whole pod unit before settling down on one.  Use this map as a guide to all the carts, (zoom in on the crowded area on the NW side). Or download this Portland Food Cart mobile app.  Nowhere to sit? Walk to your next destination at Pioneer Courthouse Square just a few blocks down the street and enjoy a prime seat on the brick steps. Before you go, don’t forget to ask for extra napkins.

Pioneer Courthouse Square, Portland Umbrella Man | itsaLisa.com

Pioneer Courthouse Square 701 SW 6th Ave. Known as “Portland’s living room,” this is where city festivals and events take place. It is also home to the famous glass Starbucks and the bronze umbrella man. Pose for a pic with him, and decide where to go next.

SATURDAY AFTERNOON: Explore On Your Own

You have a few options for the rest of your afternoon! You won’t have time for everything, so choose wisely. I have them all listed below, whatever you can’t do today you might be able to squeeze in tomorrow. Plan on each item taking 2 hours.

Portland Walking Tour: 202 NW Davis St. (Their base is right off Pioneer Square, you’re already there!) The underground walking tour is your best bet, explore the infamous Shanghai tunnels and learn about Portland’s shady past. Check before you arrive, but the tours are typically 2 hours, starting at 11:00 a.m. or 2:00 p.m. on weekends; $20 a head.

Japanese Garden, Portland | itsaLisa.com

Japanese Garden 611 SW Kingston Ave. This place is gorgeous! Walk around for hours and enjoy the nature of both Japan and Portland mixed into one epic landscape.

OMSI 1945 SE Water Ave. Explore the Oregon Museum of Science and Industry. This museum is a big hit for younger audiences; it provides a great way to learn and interact with the world around us. Engage with the latest exhibits, listed here.

Portland Art Museum 1219 SW Park Ave. Visit the exhibits for a taste of arts and culture, tucked into a quiet corner of rainy city life. Find a list of their current exhibits here.

PDX rogue

Beer Tasting Check out Rogue Brewery (1339 NW Flanders St. facts & menu) and Deschutes Brewery (210 NW 11th Ave. menu & on tapLocated just a couple of blocks away from each other, these are two of Portland’s most popular craft breweries. Ask for flights and take your palette on a taste test (here’s how) on a journey from light to dark with Portland’s finest liquid gold. Fun fact: is it you or your travel-mates’ birthday? Rogue will offer you a free pitcher – yes, pitcher – in any beer of your choice. Cheers!

Hike. Oregon is rich with hiking trails. Since you don’t have all day, choose from the hikes listed here under the “Portland Area” headline, and find what suits you. If I had to choose just one of the listed options I would choose the Mount Tabor Hike because it’s a volcano.

Dinner

Now that you’ve explored our humble city, it’s time to grab some dinner before your big night out! If you haven’t gone yet you should hit up either Rogue or Deschutes Brewery (see above) for dinner, because craft beer is a Portland must. But, if you’re fixing for some award-winning feasts, a handful of Portland’s renowned eateries are as follows…

Pok Pok, Dining in Portland | itsaLisa.com

Le Pigeon 738 E Burnside St.  French cuisine. Stop trying to pronounce “foi grois” and eat it instead.

Little Bird 219 SW 6th Ave. Le Pigeon’s little sister, also French.

Pok Pok 3226 SE Division St.  Thai food like never before.

ROE 3113 SE Division St. Japanese cuisine, hidden from the public, reservation only, kind of a big deal.

Screen Door 2337 E Burnside St. Southern cuisine, farm to fork, chicken and waffles. Worth the wait.

Slappy Cakes 4246 SE Belmont St. DIY pancake house. They provide the batter and the fixings, and you get to grill your own flapjacks at the table.

Le Bistro Montage 301 SE Morrison St.  Cajun. If you didn’t already go on Friday than I highly recommend this location for today. Macaroni is bomb. Ask to take home leftovers.

SATURDAY NIGHT: The Nightlife Tour

Get ready for some Portland Nightlife at its finest. Unless you already have a local concert or festival ticket in hand, get fancy and prepare to hit the dance floor!

PDX night life

Old Town Chinatown, NW 3rd Ave. is the place to be for a wild night. Police block off the streets with barriers so you may walk freely from bar to bar nary a concern. Explore the different venues. Let your curiosity lead the way. Is it the music that guides you? The atmosphere? The long wait to get in? Every bar has its scene.

For a more unique experience try Darcelle’s and dance with world-famous drag queens. My personal favorite venue happens to be the Barrel Room, home to a covered outdoor dance floor filled with farm tables, yes, farm tables – you’ll see. Enjoy your night and make lasting memories; Old Town Chinatown, like the rest of Portland, is one of a kind.

SUNDAY: Northwest Portland

Go ahead and sleep in. I’ve planned a nice and peaceful day for you. Or get up and at’em to hit all the stops you missed yesterday. Before you go, there are a few more must-dos on my agenda for you. I have saved the best for last. Follow my Google map under the layer titled “SUNDAY. NW PDX” for guidance.

Raspberry Macarons from Ken's Artisan Bakery, Portland | itsaLisa.com

Brix Tavern 1338 NW Hoyt St. Nourish yourself at my all time favorite spot for brunch. Brix has amazing drinks, amazing food (menu), and (if you’re up for it) they also have bottomless Mimosas on the weekends.  Enjoy doodling on the table with crayons while you wait. *Suggestion: try mapping out what actually happened last night …am I right??* The Brix Chips are amazing, think: gourmet nachos. This is breakfast, however, so perhaps try the eggs benedict instead.

After a morning well spent and stomachs well stuffed. Drive up NW Burnside into the Hillside to look out over the city among the finest real estate in all of Oregon. If you have time, check out Pittock Mansion or stroll through Pittock Acres Park. After taking in the breathtaking views head back down and explore Nob Hill. Window shop along the fine collection of boutiques on NW 23rd Street and enjoy your final hours in P-town. Here you’ll find even more coffee shops and bakeries, of course, my favorite is Ken’s Artisan Bakery, where delightful macarons are made fresh daily.

Today is your day to catch up on anything you might have missed on Saturday, but please oh please make this final destination a priority. Near the end of 23rd street you will come across the best ice cream you have ever had…

Salt & Straw, Portland's best ice cream | itsaLisa.com

Salt & Straw 838 NW 23rd Ave. “Portland’s farm-to-cone ice cream shop” and Voted “Best of the West” by Sunset Magazine. This shop puts care into every cone, you can try as many flavors as you’d like before you order, so be patient – it’s worth it!  The giant chalkboard wall behind the workers has every flavor and ingredient listed, so read carefully, you don’t want to miss a beat, or …beet. They’ve mastered the art of sweet and savory, with flavors like Honey Balsamic Strawberry with Cracked Pepper, and Salted Caramel Cupcake.  This is truly the best ice cream you will ever have. Ever.

You did it!

Congrats, you have now experienced every layer the great city of Portland has to offer. You’ve tasted their craft brews, eaten their delicacies, you’ve walked the beautiful trails and partied with the locals. I hope you had an amazing time.

Now remember, Portland has approximately 1000 bars and 2000 coffee shops (just kidding I made those numbers up), but you have a lot of options! Don’t be afraid to do your own thing, too.  This is YOUR trip afterall. This agenda is merely my insider’s perspective, the tried and true suggestions that I’ve picked just for you. So go have fun, and tell me all about it in the comments below.

…Of course now that I have written out this fantastic agenda I am extremely nostalgic. So, um, do me a favor, if you ever meet someone from George Fox University while you’re up there, tell them Lisa says hi. 🙂 Thanks!

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13 thoughts on “What to do in Portland if You Only Have One Weekend

  1. Loving your website and writings. Makes me want to visit Portland, which I can’t believe I still haven’t done yet. Something tells me it’ll feel like home. Thanks for stopping by my blog as well!

    Warmest,
    Mindy (arclinespacedot)

  2. great post!!!! If you don’t mind me asking, what modes of transportation do you think would be the most affordable to get to all these places?

    • Hi Allison, great question! Most of the stuff is downtown and easily reached on foot. Portland also has a great public transport system so you could take the MAX to any location that is a bit farther out. They even have a max that goes straight from the airport to downtown, if you’re flying in. They also have zipcars if you need something for just a few hours. Be sure to checkout the map I made on google for helpful details on where everything is located. 🙂 Enjoy!

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  4. Hi! I’ve never been to Oregon but for some reason it calls to me & I want to move there. Originally from Alabama & now I’ve lived in Wisconsin for 25 years… I love the beach & the mountains, love to hike & shop quirky & fun places, love to try food, love architecture. With this being said, I’ve talked my husband into going to Oregon for a week long trip. I have all the books from Oregon tourism but saw this post about Portland & it’s wonderful! Its like you know exactly what I love to do! Wondered if you could recommend other things to see in the rest of the state for during the week? Like is there a way to see the entire coast in 3 days? And then fit painted hills, crater lake & mt hood in too? Side note, my hobby is photography so my camera will be with me at all times! I know a week is not enough time for a beautiful state but I want to try. Thank you for any suggestions!

    • Wow! You plan on packing in a lot, but the state isn’t too big so I think you can do it. 🙂 You have to see the coast, I’d recommend Canon Beach or Oceanside, then you can go to the Tillamook Cheese factory for ice cream.

      I only lived there for 2 years with a car and spent most of my time in the city so I’m not too familiar with the rest of the area. It’s all beautiful, and this is a perfect time of year to visit. Be sure to look up the tulip fields.

      Let me know how it all goes!
      Best, Lisa

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