Portland is a city where young people go to retire

I go to Portland, Oregon, three or four times a year. I think it's a little slice of paradise, so I thought I'd share some of the things that make it so special for me.

How to get there

  • Amtrak. Take the Empire Builder west from Chicago or the Coast Starlight north from Los Angeles. The first costs 40,000 Amtrak Guest Rewards points in a bedroom (or family bedroom), and the second costs 25,000 points in a bedroom until January 24, 2016. A single redemption includes tickets for up to the maximum occupancy of the room, e.g. 2 adults and 2 children in a family bedroom.
  • Portland International Airport. PDX has flights operated by the big 3 US carriers and Alaska Airlines, as well as Southwest. From PDX the MAX light rail will take you downtown in about 40 minutes for just $2.50 ($5 for a day pass).

Where to stay

  • Downtown. I usually stay at the Hilton Portland & Executive Tower (30,000 HHonors points November-March, 40,000 HHonors points April-October), although they sometimes play games with award availability. If you're a Gold or Diamond HHonors member, you can use your continental breakfast voucher for about $12 off anything on the breakfast menu, which I recommend since the continental breakfast is terrible. If you have Starwood Preferred Guest points, The Nines is a very fine hotel, and Urban Farmer is one of the best restaurants in Portland, located on the 8th floor of The Nines. Other than that, Marriott dominates the downtown hotel scene, and their properties are overpriced, unless you're able to get an especially good deal using Priceline.
  • AirBNB. AirBNB offers two advantages over staying at hotels: you'll often pay much less than you would staying at a downtown hotel, and you can stay in the neighborhoods, which are one of the things that make Portland so great. Three fantastic neighborhoods to check out are Northeast Alberta, between perhaps 9th and 33rd Streets; Southeast Hawthorne almost anywhere East of Grand St; and North of Burnside in the Pearl District or what's charmingly called "Nob Hill."

What to do

  • The 4T Trail. Do a loop around Portland taking the MAX light rail train, the trails between the Portland Zoo and the Oregon Health & Science University, the aerial tram down to the river and the Portland Streetcar Trolley back downtown. You can do the loop in either direction, but the aerial tram is only free going downhill. Warning: bring a printout of the trail segment, or you might get very, very lost (not that I'm speaking from experience or anything).
  • ZooLights. Speaking of the Portland Zoo, every winter the Zoo is open late and lit up with holiday lights. Fun for all ages.
  • Ground Kontrol Classic Arcade. Classic arcade games from your youth and your parents' youth, plus new additions like Killer Queen, the world's first 10-player arcade game. There's a huge selection of classic and new pinball games, as well.
  • Dante's Sinferno Caberet. Sundays at 11 pm until the wee hours of the morning, a mixture of nudity, profanity, and feats of strength. The pizza joint in the corner is now operated by Lonesome's Pizza, which is excellent.
  • Clinton Street Theater's Rocky Horror Picture Show. One of the longest-running screenings in the country, doors open at 11:30 pm on Saturday nights.
  • Laurelhurst Theater and Pub. $3-4 second run movies and classics, cheap beer and great pizza. Each seat has bar space to place your pitchers, pizzas, and salads, so you don't have to juggle your dishes.
  • Look for inspiration. Part of what makes Portland so magical is that you don't need a plan to have a good time. You can walk around, make friends, check out the local alternative weekly, and wait for inspiration to strike.

Where to eat

  • Pine State Biscuits. Three locations, always lines at all 3, but always worth the wait. Go at weird times for shorter waits, go during brunch for hour-plus waits.
  • Pacific Pie Co. Two locations. Great meat and vegetarian savory pies, sweet pies, and craft beer. Save money by going during happy hour, Monday-Friday 3-6 pm.
  • Bunk Sandwiches. Five locations. The Marinated Garbonzo Beans sandwich at Bunk Downtown is way, way spicier than it has any right to be.
  • Food carts. Portland food carts are clustered into groups called "pods." Make a food cart pod the beginning or end of a walk around town and you're guaranteed to find something delicious.
  • Anywhere. Portland bars are generally required to serve hot food, and it tends to be fantastic, or at least greasy, which can be almost the same thing.

Where to drink

  • Distillery Row. Portland's craft distilleries are clustered in Southeast Portland. Visit any one to try a flight of craft liquors, or buy a Passport and drink many flights of craft liquors.
  • Swift Lounge. Craft cocktails served in large or very-large mason jars. Great food.
  • Binks. Great cocktails made with house-infused spirits.
  • Ash Street Saloon. You will never find a more wretched hive of scum and villainy.
  • Craft breweries and brewpubs. There are a lot of them, including nationally known breweries and brewpubs like Widmer Brothers, Hopworks Urban Brewery, Full Sail, and Deschutes.


Remember, the dream of the 90's is alive in Portland.