The Ultimate Guide To Portland In A Weekend: Eat, Stay & Play
This must-read weekend guide to Portland, Oregon includes things to do, where to eat, where to stay, what to pack and more!
Portland is the nation’s declared “hipster capital,” and for good reason: it’s wide selection of coffee and craft beer, outdoorsy appeal, foodie scene, and overall creativity is incomparable. Pack your bags and get ready to explore one of the most unique cities in America!
Portland, Oregon Weekend Guide
Where To Stay in Portland, Oregon
Wondering how many days you need to visit Portland, Oregon? We did this trip in a weekend and found it to be a very weekend-friendly destination. These are our suggestions on where to stay.
For those of you looking for a central place to stay with easy access to downtown and close to proximity to outdoor excursions, like the numerous waterfalls along the Oregon/Washington state border and Columbia River Gorge, I highly recommend staying in the southeast Portland district.
Bluebird Guesthouse and Evermore Guesthouse are both in an ideal location, they are extremely affordable (which is hard to come by in Portland!) and they get outstanding reviews from other travelers.
Downtown Portland – near the University – is another cool area, although parking can be a bit harder to come by and will cost you overnight. Hotel recommendations? River’s Edge Hotel and Spa gives off that Portland-esque charm, while The Benson has a vintage luxury feel to it; both hover around $200/night.
Airbnb is a popular option for accommodation throughout the entire city with which we’ve also had great experiences with (and when you sign up through our link, you’ll receive a free credit towards your stay!).
Where to Eat in Portland
Coffee and Doughnuts: If you’re dying for a taste of the infamous VooDoo Doughnuts, the best place to get them is right from the source. This place encompasses everything that is Portland — from the eclectic décor to the vegan pastries. Oh, and you can also get legally married there.
If you’re looking to venture out from VooDoo, Blue Star and 180 donuts are next best. As for coffee, nothing comes close to Stumptown Coffee Roasters. Stumptown coffee is representative of the iconic Pacific Northwest coffee scene, so stop by for a latte, take a tour of the roastery, or head over to HQ for free coffee tastings at 3pm daily. For a simple, no-frills cup of coffee try Coava or Heart Coffee Roasters, or Sterling Coffee Roasters for a latte with style!
Food Carts: Dining at a chain restaurant in Portland is a sin. Portland Mercado is a must for Mexican food lovers, while Central Eastside Food Carts has a variety of international cuisines to choose from. However, its food cart villages like Cartlandia that Portland is famous for – with 32 carts, the Blue Room Bar, and live events almost daily, this is the place to go.
As for you foodies with a more “refined” taste, check out our budget-ascending list of great restaurants below. For a sweet treat, hit up Fifty Licks or Salt & Straw – you won’t want to miss chocolate porter floats or farmer’s market-inspired ice cream flavors!
Budget-ascending list of recommended restaurants in Portland:
$: Nong’s Khao Man Gai, Rontoms, The Sudra (go at happy hour), Life of Pie Pizza, Portland Penny Diner
$$: Doug Fir (doubles as a bar and music venue!), Clyde Common, Harlow, Bollywood Theater, MÅURICE, Imperial, Deschutes (with all 26 beer varieties on tap)
$$$: St. Jack, Paley’s Place, Andina, Le Pigeon, Roe
Best Bars and Breweries in Portland
Portland bleeds beer and booze, from craft cocktails and microbrews to independent distilleries. These are the best of the best!
Bit House Saloon: Trendy restaurant/bar with great drinks and friendly staff
Multnomah Whiskey Library: Don’t mind the 1 to 2-hour wait, this experience is worth it! A wall-to-wall selection of spirits in the most upscale of venues will make for a night of whiskey you won’t forget (hopefully). Check out The Green Room downstairs for a bite and cocktail while you wait.
Bible Club: Prohibition-themed speakeasy – look for the green light in the window!
Americano: The perfect classy brunch spot to day-drink
Killingsworth Dynasty: This hipster hotspot serves up comfort vegan food to accompany your specialty drink, truly encompassing Portland’s kitschy vibe.
Radio Room: Patio and rooftop drinks with a fire pit, casual attire
The Box Social: Hidden gem with a candlelight ambience, great for a romantic night
Portland’s Distillery Row: Southeast Portland is home to eight small distilleries, making up Distillery Row. Buy a ‘passport’ for $30 to save money on tasting, and – after having it stamped at each distillery you visit – keep it as memorabilia!
Breweries: It goes without saying that Oregon has amazing beer, so it may be hard to narrow down just which ones to visit. Local favorites include The Commons, 10 Barrel, Ecliptic, and Burnside, but you can check out Portland’s beer map here to find other local breweries near your location.
Best Things To Do in Portland
Kennedy Soaking Pool: McMenamins Kennedy School is a revamped classic schoolhouse that now houses a hotel, multiple bars, and much more. The Kennedy Soaking Pool is a relaxing oasis open to the public – head there after 6pm when it’s adults-only. Afterwards, head inside to the movie brewpub, where you can have dinner and a local beer on tap delivered during your movie.
Strip Clubs: Portland is not only known for its beer and hipsters, but amazingly has the most strip clubs per capita in the U.S. as well. And yes, they cater to vegan and LGBT crowds of course!
Beer Festivals: Here in ‘Beervana’ there’s at least one beer festival nearly every month of the year. If you missed Beer Week in June, you can still make if for the annual Holiday Ale Festival the first weekend of December. There’s many more festivals changing yearly, so take a second to look online to see if any of them happen to fall during the time of your trip.
Powell’s Books: Powell’s Books, located in downtown, is known for being the largest bookstore in the world – and whether you’re a book fan or not this place is a must. Stop at the in-store coffee bar for a latte and hit the stacks. There’s a full city block of books to scan, and you don’t want to miss anything. From autographed first-editions to rare finds to author readings, there’s always something interesting going on in the Pearl Room so make sure to check it out.
Hollywood Theatre: This gorgeous 1920’s movie theatre is a Portland landmark, and shows indie films and classic movies rather than the standard latest movies. It’s a great way to mix up your typical “dinner and a movie” night out.
International Rose Test Garden: It wouldn’t be trip to the “City of Roses” without actually seeing some roses. Over 550 different varieties of roses bloom here, many of which were originally sent from foreign countries overseas during World War I. Take a self-guided tour (free!) any day of the week from 7:30am to 9pm, although street parking will cost you a few bucks so bring your quarters.
Portland Saturday Market: Vendors of every sort gather for the Portland Saturday Market, right on the river; it’s the perfect way to start your weekend. Lots of booths are cash-only, so stop at an ATM ahead of time! “Elephant Ears” are a hot commodity in the food section, but wandering around you’ll find no shortage of creativity in the clothes and craft sections as well.
Exploring the Outdoors in Portland
If you’re looking to head outdoors during your visit, Forest Park and Washington Park are both rated 5 stars by locals and tourists alike. Forest Park has miles of trails for those who want to truly immerse themselves in the greenery (wear tennis shoes!), while Washington Park is better fit for those short on time. Both parks are free, but parking at Washington will be more difficult as it’s much more crowded.
With close proximity to the coast and Washington Border, you may want to take a day to go explore what the surrounding areas have to offer. Head east to witness some stunning coastal views in quaint tourist towns like Cannon Beach or Newport, or just 20 minutes west to the towering Columbia River Gorge. Regardless of where you end up, there’s no doubt you’ll find yourself in the middle of some unforgettable adventures.
Packing Essentials for Portland
Athletic Gear: In the most outdoorsy city on the West Coast, formal or ultra-trendy attire will make you stand out – and not in a good way. To blend in, keep your clothing simple, versatile, and – when in doubt – athletic. Ladies: Black leggings paired with running shoes are completely appropriate for wandering the city during the day, and can be dressed up with cute sneakers and a denim jacket at night.
Scarf: I cannot stress enough how important it is to bring a scarf when traveling in Oregon. Although it may feel warm at times during the day, weather in Portland varies greatly and can end up being much colder than you anticipate. Rather than changing jackets – or entire outfits – throughout the day, carry a scarf that can protect you from wind and chilly nights (like this stylish scarf that doubles as a wrap shawl).
Rain-Resistant Jacket: True to stereotype, it does rain in Portland. However, if you walk around toting an umbrella to shield you from the rain the locals will laugh at you! Umbrellas are a dead giveaway of tourists. Instead, opt for a weather-resistant jacket that can wick away moisture, like this packable raincoat.
Sun Protection: Just because it may not always be sunny doesn’t mean you should skimp on sun protection. Always keep your sunglasses on hand, but apply a layer of face lotion or moisturizer with SPF every morning before heading out into the city.
Beanie: Again – because rain is common and umbrella’s are not, you’ll want something to give you a little protection from the weather. Plus, beanies will save styled hair from being ruined by humidity and moisture!
For more ideas on what to pack for Portland, read our Norway Packing Guide.
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I’m dying to go back to Portland! Would you believe I haven’t been there since college??
Love Portland! I visited about a fortnight ago for the first time and had an absolute blast. Totally agree about Saturday Market – such a great place to spend an afternoon.
I also have to put in a word for Salt & Straw ice cream though. Their sea salt & caramel ribbon ice cream is delicious. Also a night at Darcelle’s is an absolute joy!
We LOVED Salt & Straw. I guess I forgot to add it!