5-Day Itinerary in Portland: Where Food, Arts, and Nature Meet

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  • Portland, Oregon

  • City Travel

  • Food & Wine

  • Adventure Travel

  • Sightseeing

  • Local Food

  • Museums

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Fora’s Take

Portland is such a pleasant surprise! The great hotels, restaurants, mix of art, culture and nature truly makes this place so special. From live comedy, to world-renowned donuts, botanical gardens, galleries and famous brewers, there is never a dull moment!

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Where to stay

McMenamins Crystal Hotel

Located in downtown Portland’s West End, on the edge of the Pearl District, in an area that could be renamed “rock ‘n’ roll row," this century-old flatiron classic, has 51 rooms, each decorated to honor a song or performance from the neighboring Crystal Ballroom's glorious past 100 years.

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Day 1: Arrive in Portland

long old school vertical sign over a theater reads, "portland" in white letters, surrounded by large glass high rise buildings

Arrive in downtown Portland early Friday evening and check into McMenamins Crystal hotel! Grab a dinner & a drink at Zeus Cafe - their all day breakfast, lunch, dinner and bar spot! Around the corner is Al’s Den, also part of McMenamins, which does live comedy on Friday and Saturday nights. Walk to this corner and down the stairs to purchase tickets and drinks! The local live comedy is a blast!

Day 2: A Waterfall Getaway

a small waterfall crashes into water below with a bridge above between two mossy rock walls

Grab breakfast at Cheryl's on 12th. They have a wide variety of options that are friendly to vegans and non-vegans! After this, head to Multnomah Falls with Hub Worldwide Tours — they do amazing half-day educational tours that show you 10 unique waterfalls and educate you on the local history! After your tour, they will drop you off at McMenamins, where you can put on a bathing suit and go into the salt baths! Truly so relaxing and lovely after a day of exploring the wilderness! Dinner should be at Portland City Grill, located on the 30th floor of the US National Bank Building that locals call “big pink” because the windows are all tinted pink! You get a 360 view of Portland, which is absolutely breathtaking!

Day 3: Explore the Pearl District

facade of a light brick building with fire escape and lit up windows

Head to Screen Door for brunch — they have amazing mimosas and food! Then walk around the Pearl District — the local shops are fun and express Portland’s arts! Von Ebert Brewing is the place to go for lunch! They have award winning beers and burgers! After this, head to Old Town Brewing for a haunted underground tunnel tour! Truly amazing and educational! You get free beer after and can buy their famous pizza for dinner!

Day 4: But First, Donuts

pink neon sign reads, "voodoo donuts" with a spooky ghost like cartoon

Head to Voodoo Donuts and try the world renowned donuts! They have a full vegan menu now, which is amazing! After this walk over to the Chinese Garden where there is a guided audio tour and a tea cafe where you can get authentic tea and play games! Head back to the hotel and stop off at a brewery or two on the way — I recommend Deschutes! Get ready for dinner and head to Jake’s across the street! They have amazing Irish coffee and top class seafood!

Day 5: Game night

red neon sign reads, "cafe" outside a dark bar

Wake up and enjoy the free air Portland has to offer on your last day! Try catching a Trail Blazers game if you can! Mox Boarding House has a variety of board games that you can play while sitting in an upscale booth and ordering food and drinks! If there is a UFC fight night, Suki’s plays all fights with a $10 admission fee!

Need to Know

For more travel tips, check out Fora Advisor Lizz Callaway's guide to Portland: Discovering Small Business Charm in Portland, Oregon.

This guide is part of our ongoing series on travel to Portland, Oregon.

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