A Weekend In Portland You Won’t Forget

Sharing is caring!

This post may contain affiliate links. If you use these links to buy something I may earn a small commission at no additional cost to you. Thanks.

If you’re planning to spend a weekend in Portland, Oregon, you’re in for a real treat! This guide will cover everything you need to know, including unique attractions, quirky restaurants and bars, and tips for visiting this gem of the Pacific Northwest.

Few cities can match all Portland has to offer, with something for everyone whether you’re a foodie, a lover of music and culture, an adventurer, or all of the above! With so many things to do and see, a weekend in Portland is nothing if not memorable.

A weekend trip to Portland can be just what the soul requires if you find yourself stuck in a rut and in need of inspiration. You can see all the best bits of the PDX over the course of a long weekend, with a 3-4 day Portland itinerary being pretty ideal. Even so, you can still squeeze a lot into a 2-day trip if that’s all you have time for!

This handy guide will help you plan the perfect Portland weekend trip, from what to do and where to eat, to getting around the city with ease!

Know Before You Go

Before you spend a weekend in Portland, here are some helpful tips to keep in mind:

Is Portland safe to visit? Absolutely! No city is completely crime-free, but common sense and a bit of research will help ensure your trip goes smoothly. This guide to Safety in Portland addresses some FAQs you may find helpful!

Expect to spend $180+ per day! While expenses will vary greatly depending on your preferred style of travel, you can expect to spend around $180 a day, taking into account accommodations, attractions, transportation, and food.

This is a walkable city! You will have no trouble getting your daily steps in while visiting Portland. The city and its surrounding attractions tend to be easily accessible by foot, but if that doesn’t work for you there are always bikes, cars, and public transport!

Nature is all around! Even in the city! There are hiking trails that are accessible right from Downtown Portland that lead to many attractions like the Pittock Mansion, Hoyt Arboretum, the Oregon Zoo, and more!

Expect rain, but not that much. While Portland is often hailed as a “rainy city” on paper, the weather is much more mild than most people realize. It may drizzle on and off, primarily in the colder months, but heavy downpour tends to be relatively uncommon. You could spend a weekend in Portland without any rain at all!

Get Packed

Portland is a diverse and laid-back city. You’ll see some chic outfits but you’ll see a lot of flannels and jeans too, as well as some rather eccentric choices that no one bats an eye at. So, ultimately, pack whatever you’re comfortable with because no one cares what you’re wearing.

• As I mentioned before, this is a very walkable city, so wear good shoes!
• Depending on the time of year, you may find yourself needed a raincoat and a pair of sunglasses on the same day. The weather is subject to change, so make sure you’re always prepared.
• Bring reusable bags for your grocery shopping needs! Like many places here in the States, single-use plastic bags have been banned, so plan accordingly.
• Need more help packing? Check out my minimalist packing list for female travelers.

Get In The Mood

Indoor Things To Do In Portland

Smith Teamaker

Smith Teamaker is an absolute must-do if you’re a tea fanatic, such as myself. They have two tasting rooms in Portland, but I recommend the one on 23rd St. because it’s in the Alphabet District, which is so fun to explore. Both locations have a rotating menu of seasonal teas, as well as their everyday selection which has something for everyone. While you can order lattes, matcha, and even cocktails, I can never decide on just one drink so I like to do their tea flights.

I loved the experience at their tasting room so much during my first weekend trip to Portland that I had to move my itinerary around to free up an afternoon to go back a second time! To this day, I have their teas shipped to me regularly because the quality really is unmatched. This is my favorite place in Portland so I really can’t recommend it enough!

Pittock Mansion

If you’re eager to get a dose of local history, you can’t pass up the Pittock Mansion. This Edwardian-era chateau tells the story of how the Pittock family helped Portland transition from a small pioneer town to a bustling metropolis. If history isn’t your thing, the beauty of this opulent estate is reason enough to visit! Once you’ve toured the house, make sure to take a stroll around the grounds, where you can get a great view of the city.

You can expect to spend about an hour here if you do the self-guided tour, and tickets range from $11.50-$15.50. Their hours vary throughout the year so be sure to check the Pittock Mansion website while planning your visit. I also recommend seeing if any of their events or special exhibits are taking place during your Portland weekend trip!

Powell’s City of Books

Powell’s City of Books is one of the coolest bookstores I’ve ever been to, rivaling only the Last Bookstore in Los Angeles in terms of uniqueness, but in terms of size, there’s no comparison. In fact, it’s the world’s largest used & new bookstore. It spans an entire city block and has 3500 different sections to explore, housing over 1 million books!

Powell’s has two additional smaller locations in Portland, but the one at 1005 W Burnside St. is the one you want!

Pro Tip: If you’re planning to visit the rare book room, you’ll need to obtain a pass from the information center in the Pearl Room. The rare book room is only open from 10:00-5:00 and capacity is limited to 14 customers at a time, so plan accordingly!

Rimsky-Korsakoffee House

How does one even begin to describe the vibe at Rimsky-Korsakoffee House? Located in a supposedly haunted craftsman-style house dating back to 1902, this is one of Portland’s oldest (and quirkiest) coffee shops. They’re known for their eclectic, spooky, and downright weird decor, as well as some of the best drinks and desserts Portland has to offer.

The name pays tribute to the Russian composer, Nikolai Rimsky-Korsakov, and you’ll notice little homages to classical music all around the shop. Sometimes they even host live classical music performances, so be sure to tip the musicians!

This is a cash-only establishment, so come prepared! There is no ATM on the premises, but there’s one at the convenience store just next door. They’re closed Monday and Tuesday but are open every other day from 7:00 PM until 12:00 AM.

Movie Madness Museum

If you saw my weekend guide to Austin, Texas, you may remember I paid a visit to I Luv Video, the “oldest and largest video store in the world”. Well, while Movie Madness Video might not claim the title of the oldest or largest video store, it is home to over 90,000 DVDs, Blu-rays, and VHS tapes available to rent!

In addition to movie rentals, Movie Madness houses an impressive collection of classic movie memorabilia in display cases throughout the store. The collection includes costumes and props from modern classics such as Pulp Fiction, Fight Club, and The Godfather: Part II, as well as pieces from classics like Citizen Kane, Psycho, Casablanca, and films from the Silent Era.

They also host weekly movie screenings, so you can call them at 503-234-4363 to see what’s playing during your Portland weekend trip and to reserve your ticket. Admission is free for both the museum and movie screenings, but donations are encouraged. With so few of these movie rental stores left around the country, it’s important we support institutions like this one!

If you love old Hollywood, make sure to pay a visit to some of the many Celebrity Gravesites LA has to offer next time you’re in Southern California!

Freakybrutte Peculiarium

The Freakybrutte Peculiarium is home to a gallery of eccentric art, as well as several interactive exhibits and photo opportunities. You can expect to find all kinds of oddities, sci-fi memorabilia, and goofy souvenirs here, as well as ice cream sundaes featuring different kinds of bugs. Is it kitschy? Yes. Campy? Yes. But that’s all part of the charm.

You can expect to spend about 30 minutes here as the museum is relatively small. This is a family-friendly attraction with no age restrictions, although children younger than 8 may find it a bit too scary due to the monsters, aliens, bugs, etc. Tickets are $10 per person or $7 on Tuesdays, but admission is free if you come in a [family-friendly] costume.

Outdoor Things To Do In Portland

Lone Fir Cemetery

Lone Fir Cemetery is not only the final resting place of 25,000 people, it’s also Portland’s second-largest arboretum. As the name implies, there was a time when this cemetery had only a single fir tree, but now it is home to more than 67 different species of trees, with over 700 trees in total! Whether it’s the beautiful trees or the historic graves that appeal to you, this is a great place to take a stroll during your weekend trip to Portland, and is, of course, totally free to visit.

Hoyt Arboretum

Alright, so I mentioned Portland’s second-largest arboretum, now here’s the first. Founded in 1928, Hoyt Arboretum is home to an impressive 2300 different species of trees and shrubs from all over the world. If you’re up for a good hike, you’ll appreciate that there are 12 miles of trails to explore. They have several different routes mapped out for different levels of experience, the easiest one being only a 30-minute loop.

This gorgeous retreat into nature is conveniently located just a few minutes from Downtown Portland. It’s open year-round, and always free to visit!

Multnomah Falls

Multnomah Falls is not only the tallest waterfall in Oregon but also one of Portland’s most recognizable landmarks. This natural wonder is more than 600 feet tall and is a sight to behold, whether you hike to the top or just admire it from below.

This is one of Portland’s most popular tourist attractions, and it does get quite crowded. Because of its limited parking lot and the fact that it’s located about 30 miles east of the city, I recommend taking a shuttle or a guided tour. If you choose to drive, you may be required to purchase a parking permit, depending on the time of year.

International Rose Test Garden and Washington Park

The Internationa Rose Test Garden is located within Washington Park. Much like Balboa Park in my hometown of San Diego, Washington Park is home to museums, picnic areas, the Oregon Zoo, the Portland Japanese Garden, and much more! You could spend a whole day seeing all this park has to offer, but if you only have time for one stop during your weekend in Portland, make it the International Rose Test Garden. This historic garden dates back to WWI and exists as a testing ground for new varieties of roses, with over 610 different varieties of roses blooming throughout the year. Oh, and admission is free!

Quick Sights To See

Mill Ends Park

Did you know that Portland is home to the world’s smallest park? It’s true, Portland’s Mill Ends Park has held the Guinness World Record since 1971. It’s located in the center median of SW Naito Parkway in Downtown Portland, adjacent to Governor Tom McCall Waterfront Park.

Ace Hotel Photobooth

What’s so special about a photo booth? Well, for photography buffs, this one is worth the visit. This vintage photo booth relies on darkroom technology to print and process its photos – a rare find these days! No fancy effects, colored ink, or digital elements, just good old-fashioned chemistry.

The photo booth is located right next to the entrance of the Ace Hotel lobby and is open to the public, for the small price of $4. You may want to plan your 4 poses ahead of time because it doesn’t give you much time in between shots. It’ll take about 3 minutes to print your photos (which, you’ll understand, is actually quite an impressive speed if you’ve ever worked in a darkroom before). Sit back on one of the super comfy couches, relax, and prepare your nostrils for the bitter, chemical scent of nostalgia.

Witch’s Castle

Despite the whimsical name, the origins of this structure are disappointingly mundane. It was built in the 1930s and used as a ranger’s station and bathroom for hikers until a storm in the early 1960s left in in disrepair. In the 1980s it became a popular spot for high school kids to party, and, naturally, rumors of it being haunted began to spread.

Unfortunately, there’s no way to avoid taking a (relatively easy) hike if you plan to visit the Witch’s Castle. The shortest trail is a half-mile long and is accessible from the Upper Macleay Parking Lot near the Portland Audubon Society.

Day Trips To Take From Portland

Timberline Lodge

The Timberline Lodge is a great spot to head to if you fancy a bit of skiing, but it’s the connection to Stanley Kubrick’s masterpiece, The Shining, that makes this an exceptional getaway. The lodge served as the exterior for the Overlook Hotel, and if you’re a film buff, you won’t be disappointed by the gift shop and familiar views.

This icon of American horror is just a short road trip away, about an hour and a half from the city by car. It’s the ideal getaway for a short weekend in Portland. Make sure you grab a cup of their hot cocoa because it’s the most satisfying thing you’ll ever drink!

Salem

Oregon’s capital city of Salem is just about an hour’s drive south of Portland and makes a great day trip. It’s a much smaller city than Portland and makes for a nice break from the hustle and bustle.

The Oregon State Hospital is not for the squeamish, but if you can handle the dark history of mental health treatments in this country, it’s a truly fascinating museum (and it’s where One Flew Over The Coukoo’s Nest was filmed, and the setting of Mary Ellen Mark’s infamous documentary photography series, Ward 81.)

Seattle

Seattle is a fantastic city that absolutely cannot be skipped if you hope to get the full Pacific Northwest experience. While you could easily plan a separate trip entirely dedicated to Seattle, it also works well as a day trip as it’s only about a 4-hour drive from Portland. Check out my Seattle 4-Day Itinerary for some trip-planning inspiration!

Where To Eat & Drink In Portland

Fun fact about Portland: Bars are required by law to serve food, which means you’ll never have to choose between drinks or dinner! Aside from bars, there are countless wineries, breweries, and restaurants to explore throughout your Portland weekend trip!

McMenamins Kennedy School

If you heed one piece of advice from this whole post, let it be this: If you see the name “McMenamins” anywhere, you go inside. This chain of breweries, pubs, hotels, and more is one of the things I love most about the PNW. Each location is totally unique, many of which are located in historic buildings such as theaters, churches, and schools.

My favorite is McMenamins Kennedy School, a historic former elementary school dating back to 1915. What’s great about it is that there are six different bars and restaurants within the school, each with its own menu and theme. If you’re hungry I recommend making your way to the Cypress Room for dinner and a beer before heading to the Detention Bar for a bit of trouble.

Cheese & Crack Snack Shop

For light snacking, there’s no better place to stop on your weekend trip to Portland than Cheese & Crack Snack Shop, in my opinion! They have delicious soft serve ice cream, wine & beer, and cheese plates that are crazy good. The brie brûlée is a must-try!

Bartini

Bartini is located inside Urban Fondue, and it’s amazing! This dimly lit bar is moody and low-key, perfect for a relaxing night out. They have an extensive menu of unique martinis and cocktails, and lots of foods to munch on like tacos, sliders, and the best damn fondue I’ve ever had! The Oregon black truffle and the brie & gorgonzola fondues changed my life.

Marco’s Cafe

Marco’s Cafe and Espresso Bar is a total gem in the heart of Multnomah Village, a charming neighborhood about 15 minutes from Downtown Portland by car. This cozy cafe is the ideal brunch spot on a drizzly day and their whimsical decor features inspirational quotes along the walls that lovers of classic literature will appreciate.

The food is even more swoon-worthy than the decor, and their menu includes some incredible drink options like mimosa and Bloody Mary flights, as well as excellent coffee. They also have great kid-friendly options like hot buttered noodles, chicken strips, French toast, and more!

Quick Bites

If your itinerary is too full to squeeze in time to enjoy a meal at a sit-down restaurant like the ones mentioned above, consider some of these grab & go treats.

• Burgerville: This local fast-food chain makes some of the best burgers I’ve ever had, and with drive-thru locations all over the city you won’t have to look very hard to find them!
• Voodoo Doughnuts is very popular among tourists, but Blue Star Donuts and Mikiko Mochi Donuts are great alternatives if you prefer to stray from the beaten path!
• Salt & Straw: Other cities may have Salt & Straw locations these days, but it all began in Portland! Their rotating menu of unique ice cream flavors makes them well worth the visit!
• Poplandia: If you love gourmet popcorn you have to pay a visit to Poplandia. They have a wide variety of flavors including butterbeer, orange sea salt caramel, garlic cheese, Mayan hot chocolate, and more!

And, of course, I can’t forget to mention Portland’s food carts. Food trucks are a massive part of Portland’s foodie culture, but they’re more commonly called “food carts” here. There are a ton worth visiting on your weekend trip to Portland, but I recommend consulting FoodCartsPortland.com to find the ones that look best to you.

Getting Around Portland

Getting around during your weekend trip in Portland is one thing you don’t have to worry about as there are many options for navigating the city.

Renting a car is one option, or you can utilize rideshare apps like Uber and Lyft. If you do end up renting a car, make sure to download the Parking Kitty app so you can easily add more time to your parking meter directly from your phone.

Bike rentals are a great option for getting around the city, and can definitely save you money in the long-run with options as low as about $16/day.

Portland’s public transportation system, Trimet, is affordable, easy to navigate, and provides several options for getting around such as busses, street cars, and the MAX Light Rail. MAX, or Metropolitan Area Express, is the local train system and the best way to travel far & fast. They even have a train that will take you straight from the Portland International Airport all the way to Downtown.

Tips For Driving In Portland

• First and foremost, it’s important to know that unmarked cop cars are legal in Oregon and are often used for traffic enforcement. If you find yourself being pulled over and have any doubts about whether it’s an official law enforcement vehicle, you can turn on your hazard lights and call 911. They’ll be able to confirm whether or not the vehicle is an official cop car.
• You may be surprised by how congested traffic is in Portland around rush hour, so always make sure you give yourself some wiggle room if driving to any time-sensitive events or attractions.
• If you’ve heard that it’s illegal to pump your own gas in Oregon, that was in fact true up until recently, but as of 2023, it’s not required to let the gas station attendants pump your gas for you.
• Keep an eye out for pedestrians and bicyclists during your Portland weekend trip, because there will be many!

Where To Stay

Location: Location may be the biggest selling point for the Ace Hotel, which is located right in the heart of Downtown, but it doesn’t stop there. The hotel is incredibly stylish, with comfortable accommodations and all the modern amenities. They’re also pet-friendly, and very affordable! If you arrive early you can enjoy a drink from Stumptown Coffee, or take a walk to Powell’s City of Books, which is just a block away!

Luxury: The Nines is a fashionable, upscale hotel with modern art installations everywhere you look, as well as a gorgeous rooftop lounge and an idyllic view of the city. They have comfortable, uniquely designed rooms and excellent dining options. This hotel is also in the heart of Downtown, so the location is an added bonus to their luxury-forward accommodations.

Charm: As I mentioned before, McMenamins Kennedy School is an excellent spot to grab dinner and drinks during your weekend trip to Portland, but it’s also a hotel! Their rooms are charmingly decorated, and with the dining options and history behind this former Edwardian Era school, you’d be hard-pressed to find a more unique place to stay. It’s located in a more slow-paced residential area than the other two options I mentioned, which means you’ll have to do a bit of traveling to see a lot of the sights, but the neighborhood it’s in is definitely worth exploring as well!

Coolest Neighborhoods In Portland, Oregon

Alphabet District

The Alphabet District, located just outside of Downtown, is a trendy and charming neighborhood featuring beautiful Victorian homes, eclectic shops and boutiques, as well as excellent coffee shops and restaurants.

Pearl District

The Pearl District is where you’ll find some of Portland’s most renowned art galleries, parks, restaurants, and fashionable shops.

Hawthorne

Hawthorne is known for its bohemian vibes, thrift stores, theaters, and nightlife. They have a lot of laid-back pubs and restaurants where you can find lots of vegan and gluten-free options, burger joints, and some surprisingly good taco shops.

When To Visit

The best time to take a weekend trip to Portland heavily depends on what you’re hoping to experience, as there really isn’t a bad time to visit.

If you hope to do a lot of adventuring and outdoor activities, summer is the best time to come. Certain attractions, such as shuttles to Multnomah Falls and the Portland Saturday Market tend not to operate during the colder months.

However, that doesn’t mean the colder months aren’t without their charm! Autumn in Portland is stunningly gorgeous, which is why it’s my favorite time to spend a weekend in Portland. I also think Portland is one of the best US cities to visit in winter if you’re looking to enjoy some sweater weather activities without having to worry about major snowstorms messing up your plans.

Pro Tips

• Want to explore Portland’s food carts but don’t know where to begin? A guided food cart tour might be the perfect option for you!
• One thing to love about a weekend in Portland is that there is no sales tax!
• In addition to their annual “naked bike race”, Portland has more strip clubs per capita than any other US city, as well as many drive-thru “bikini barista” coffee huts. Do with that information what you will.
• Portland is known for its friendly, genuinely nice residents. In my experience, the rumors are all true.

FAQs

🌊 If you like this guide to a weekend in Portland please don’t forget to like and share! If you do any of the things I recommended use the hashtag #theseasidecalls so I can share with my followers!

Sharing is caring!