The Perfect Weekend in Portland Itinerary

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Echoing Austin, Texas’ hipster oasis, the Rose City’s motto, “Keep Portland Weird,” sums up its distinctive character, one affectionately satirized in the cult favorite TV show Portlandia. But Portland’s quirkiness isn’t its only quality. Far from it. This modern metropolis, a gem of the Northwest, is also famous for its incredible foodie scene, eco-consciousness, gregarious locals, and much more. If you’re planning a weekend in Portland itinerary, read on to find some of the must-see attractions in this delightfully, proudly off-beat city. 

When to Visit Portland 

Like its infamously rainy northern neighbor Seattle, Portland, too, upholds the Pacific Northwest’s cold, damp stereotype for much of the year. You’re almost guaranteed to see some rain, no matter when you visit. 

Bring a jacket and, as long as you don’t mind standing out, an umbrella! Pacific Northwesterners are weirdly umbrella-averse. I don’t know why. It’s just how it is. We’ll walk in a literal downpour with our hoodie pulled way up over our beanie-clad head, soaking wet, and act completely unbothered. Don’t be like us; umbrellas exist for a reason. 

However, it’s not all rain all the time. You can expect some days that exceed 90°F (32°C), chilly mornings, and cool nights on any given summer weekend in Portland. 

Late spring, summer, and early fall are undoubtedly the best times to visit, not just because of the sunshine. It’s also when the rose, rhododendrons, and other flowers that line the city streets and urban gardens will be in full bloom, making the already-colorful city extra bright. 

This is also prime time for outdoor events and festivals. 

If you visit in winter, expect to be cold and wet (like, really wet). The good news is Oregon’s coast and near-coast region doesn’t usually drop to freezing during winter, meaning you should be safe from snow and ice. If you want that sort of thing, though, Mt. Hood isn’t far! 

Driving along the Oregon Coast to Portland
Driving along the Oregon Coast

Getting To and Around Portland

As its name denotes, Portland is and always has been a significant transport hub. But not just for seafarers. It’s also well-connected to the region via a train station, numerous buses, and an international airport. It’s also just under three hours’ drive from Seattle

Portland is relatively easy to navigate. The MAX light rail from the airport to downtown takes about 38 minutes and costs about $2.50, or you can Uber or Lyft if you don’t have a car. 

While traffic can be heavy, it’s not as bad as that of nearby Seattle. Most people walk or cycle everywhere or take public transport. 

The city’s stellar public transit network consists of MAX light rail, streetcars, and commuter rail, making it easy to get around the city proper. If you’re going to stay within city limits, you really don’t need a car at all. 

Most tourist attractions in the Rose City are located on the west side of the Willamette River and neighborhoods like downtown, the Pearl District, and Nob Hill. If your home base is in this area, you can walk or cycle most places. 

The Rose City is famously bike-friendly, yet unlike some cycle-centric metropolises (Amsterdam), you’re not likely to get hit by a bike if you do prefer to hoof it. If you didn’t bring a bike, you could rent one for a few hours, the day, or the weekend from providers like Bike Town. 

If you want to venture outside the city to the Oregon Coast or even down to San Francisco, which I can’t recommend strongly enough, a car will be helpful. You can rent one through if you don’t have your own. 

Don’t fret if driving isn’t your thing, though! There are buses to some of the best destinations, like Seaside and Cannon Beach. A Greyhound from Union Station to Cannon Beach costs about $17 and takes about two hours. Just be prepared to navigate a sporadic bus system once you get to your destination or walk/taxi everywhere. 

Cannon Beach
Nearby Cannon Beach

Weekend in Portland Itinerary

There’s always something happening in The Rose City, and you may find it’s hard to fit in everything you want to do in just one weekend. But if you do only have two days in Portland, here are a few stops you won’t want to miss. 

Day 1 – Doughnuts, Bookshops & Museums!

Voodoo Doughnuts 

The first stop on your Portland itinerary is the city’s most famous and beloved doughnut shop, Voodoo Doughnuts, where you can grab a breakfast pastry and coffee. 

Kenneth “Cat Daddy” Pogson and Tres Shannon, two entertainment-minded entrepreneurs, opened the first Voodoo Doughnuts in 2003. At the time, there wasn’t a single doughnut shop in downtown Portland, so you can imagine the craze that erupted when a shop as wacky as the city itself opened up and started serving up delicious pastries in a medley of classic and unconventional flavors. 

Within a month, the shop had achieved a national press mention and a loyal, die-hard following at home. They’re now world-famous and an absolute must-stop on any Portland weekend itinerary. 

If you’re still hungry or the line at Voodoo is absurdly long, head to Blue Star. While Voodoo’s patrons are about a 50/50 mix of tourists and locals, many Portlanders eschew the shop, insisting Blue Star is far better. 

The lesser-known but no less tasty Blue Star serves up various tantalizing flavors, including Cointreau Crème Brûlée, maple bacon, Valrhona chocolate crunch, and The O.G., featuring an orxata (horchata) glaze. 

If you’re really into your doughnuts you can even do a doughnut tour!

Portland Old Town Sign
Portland Old Town – the home of the original Voodoo Doughnuts

Powell’s Books 

Powell’s Books is heaven for bookworms. The world’s largest independent bookstore, it is undoubtedly one of Portland’s most prized assets and another quintessential stop on a Portland, Oregon itinerary. 

The shop spans an entire city block and is packed with a vast array of new and used books in every genre. 

Grab a basket; you’ll need it to carry everything you pick up as you browse the labyrinth. 

Powell’s is also famous for its rare book room, featuring rare first editions and signed copies of antique and contemporary titles. 

After checking out, head to the café to rest for a bit and have a bite and a coffee. You’ll need to re-energize after spending a couple of hours wandering the store! And yes, you will probably be drinking a lot of coffee on your weekend in Portland. When in Rome… 

An Afternoon at the Museum 

Before heading out to get a taste of Portland’s vibrant nightlife, check out one (or both!) of the city’s most prominent museums. 

The Oregon Museum of Science and Industry features various temporary exhibitions throughout the year and the Natural Science Hall, Empirical Theater, USS Blueback Submarine, and Kendall Planetarium. 

Learn about everything from ancient natural history to contemporary scientific innovations and get lost in the mind-blowing vastness and complexity of the night sky. 

Founded in 1892, the Portland Art Museum is one of the West Coast’s oldest art museums. 

It features various temporary exhibitions featuring world-renowned artists in painting, print, mixed media, film, and more. The museum also houses permanent collections, including Native American Art, Asian Art, Northwest Art, European Art, American Art, and Photography. 

Fancy a history lesson? Check out Pittock Mansion, which offers an immersive look at the city’s past in the setting of one of its oldest and most beautiful historic homes. The mansion also has a fantastic view of the city! 

Lawn and building of Pittock Mansion
Lawn and building of Pittock Mansion

Enjoy Portland’s Nightlife

People joke that everyone in Portland is a barista, in a band, or both. And it’s not that far from the truth. There’s pretty much always a live show going on somewhere. 

On your first night out, head to a venue or go bar-hopping and let yourself get swept into the vibrant nightlife scene. 

Oregon Public House is a great place to start. The family-friendly pub, open from 4-9:30 p.m., donates all profits to local charities and is a popular meeting spot for non-profits. Start your evening with a delicious meal and a drink while giving back to the community in the process! 

Then head to Alberta Street, the place to be for hip, local flavor. Start at Alberta Street Pub, a high-end establishment with a terrace perfect for sipping a cocktail on a summer evening. Then, stop by Radio Room, an art deco-themed bar with vegan treats and seasonal cocktails.

Next Is Bye and Bye, a Southern-inspired bar with superb vegan cuisine. If it wasn’t clear by now, Portland is also one of the easiest places to be a vegan tourist! 

Also on Alberta Street is Alleyway Bar, which is a bit grungy in the best possible way and often hosts live music. 

McMenamins Crystal Ballroom, Revolution Hall, Alladin Theater, Dante’s, and Mississippi Studios are other hot spots for live music. Grab a copy of Portland Mercury to see what’s happening on any given evening. 

Portland at Night
Portland at Night

Day 2 – Food Trucks, Parks & Arcades

Check Out the Food Truck Scene 

The Rose City is a foodie paradise, with a vast array of establishments from small cafes to Michelin restaurants. 

For the second half of your 48 hours in Portland, grab brunch at a food cart. 

Portland famously has the most strip clubs per capita of any U.S. city, about twice as many as public restrooms. But it’s also home to one of the nation’s biggest food truck scenes! 

More than 600 food trucks throughout the city dishing up every kind of cuisine imaginable, from Korean to Ethiopian to and down-home barbecue to vegan pizza. Seriously, they have it all. 

Unlike most food truck scenes, Portland’s are not mobile. Instead, they are organized into stationary “pods.” You can find a map of all the carts here, divided by categories to make finding your next meal a cinch. 

You won’t get to try them all on your weekend in Portland, but you can try at least a few throughout the day! According to locals and critics, some of the best include Yoshi’s Sushi, Farmer & the Beast, Bing Mi, Matt’s BBQ, and Baby Blue Woodfired Pizza. 

Washington Park 

Next up on your Portland weekend itinerary is a stroll through Washington Park. 

This urban green space is massive, with a zoo, arboretum, amphitheater, children’s museum, Japanese Garden, and International Test Rose Garden. The latter two are especially worth a visit. 

The Japanese Garden comprises 5.5 acres with impeccably landscaped greenery and water features, and a tea house. 

The International Test Rose Garden features more than 10,000 roses in over 650 varieties of numerous colors and styles. This is reason enough to come in summer! June is peak bloom season, but there will likely be sweet-scented blossoms in late April through early October. 

Japanese Garden in Portland
Japanese Garden in Portland

Ground Control 

Want to feel like a kid again during your 2 days in Portland? Head to Ground Control, the family-friendly, nostalgia-inducing vintage-meets futuristic arcade. It’s usually open from midday ‘til late. 

With an arcade and video games, pinball machines, and a dance mat, it’s the perfect spot to spend a couple of hours on a rainy afternoon! 


Next on your Portland itinerary, grab a bite or a drink at McMenamins. 

McMenamins is a local chain of family-owned establishments, primarily hotels, restaurants, and bars, located in repurposed or rejuvenated historic buildings. Each location is unique, with distinct features reflecting the city and its history. 

McMenamins Kennedy School is one of the best. Located in a former abandoned elementary school, it might sound like the stuff horror movies are made of.

But there’s nothing spooky going on here unless there’s a scary flick showing at the in-house movie theatre. Besides the cinema, there’s also a hotel with unique rooms that evoke a sense of school-age nostalgia, a pool, a bar, and a brewery. 

McMenamins Crystal Hotel, next to the Crystal Ballroom, in the Pearl District, the White Eagle Saloon & Hotel, and St. Johns Theatre & Pub are other popular McMenamins locales in Portland. 

Portland comes alive at night!
Portland comes alive at night!

Have More Than 2 Days in Portland?

After two days in Portland, you’ll more than likely wish you had more time! If you do and the weather is nice, take advantage of the city’s status as one of the best spots for eco-tourism in the U.S.! 

If you’re craving something unusual and distinctly Portland, take a short but somewhat challenging hike up to Witch’s Castle. The “castle” doesn’t have anything to do with witches. But the abandoned structure has had many unpleasant lives throughout the past 150 years and is said to be haunted.  

A bit further afield, there are multiple spots to check out the Pacific Northwest’s beauty along the Columbia River, at Multnomah Falls, Silver Falls, Hood River, or Mt. Hood. 

A little further still, but so worth it, is the stunning Oregon Coast, with vast stretches of sandy, atmospheric beaches and quaint towns like Seaside and Astoria.  

Mount Hood
Mount Hood

Where to Stay in Portland

If you’re looking for a great place to stay during your weekend in Portland, you really are spoilt for choice. There are countless great places to rest your head in the Rose City and if you’re looking for something great, check out these suggestions:

The Society Hotel — Situated within easy walking (or cycling!) distance of the Rose City’s top attractions, this chic hotel is perfect for those looking for a great place to stay. There are a number of rooms available and also a restaurant on site. Click here to see their availability

Kimpton Riverplace Hotel — If the life of luxury is more your style for your Portland itinerary, then you can’t go wrong with this great hotel. Located on the banks of the Willamette River, there are a number of plush rooms available and countless other amenities to ensure your stay is a luxurious one. Click here to see their availability

Travelers House — For those travelling on a budget or solo, then this hostel is a great choice for you. They offer both dorm beds and private rooms and there are also some great self-catering facilities and common areas to make meeting other traveller’s a breeze! Click here to see their availability

Private Rental — If you’re after a bit of privacy in Portland or would rather a more “local” feel, then a private rental is the choice for you! There are a myriad of great properties in the Rose City, like this quaint, centrally located house. Click here to find the best private rentals in Portland!

Not quite what you’re looking for? Click here to browse more hotels in Portland!

Portland, Oregon
Portland, Oregon

Planning the perfect weekend in Portland itinerary really isn’t a hard task as there are so many amazing things to do in this Pacific Northwest city.

Are you planning to spend 2 days in Portland? Have any questions about this itinerary? Let us know in the comments!

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Kate Daniel is a writer for The World Was Here First. Originally from Washington State, she is a slow traveler and digital nomad. When she isn't writing, she is most likely befriending stray cats or sitting by the sea and daydreaming about the next adventure while eating copious amounts of fruit.

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