Guide to Portland in a Weekend

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!



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!).


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