Everyone has a city that they keep going back to. A city that’s not too big and not too small. A place where people ring their bike bells in a friendly way, and where thick glasses and vintage polyester pants are always the look. A little part of the country where you can bury yourself in the back of a book store with coffee in a chipped mug and a vegan scone leaving a crumb trail like the mythical Hansel and Gretel.

For me, my magical little forest city is Portland, Oregon.

And it’s so easy to plan a trip here. If you fly in, you’ll probably connect in Seattle before transferring to a funky little plane that bounces around good-naturedly before touching down at the cutest little airport you’ve ever seen. If flights are full from Seattle, hop on BoltBus, Greyhound Bus or Amtrak and arrive in just a few hours.

There are a lot of great little boutique establishments in Portland (and AirBnB for the budget traveler), but The Ace Hotel is a landmark. Entering, you’ll notice hip Portland residents lounging on the couches in the lobby, enjoying espresso from adjacent Stumptown Coffee. Grab a macchiato and lounge with the locals for a few minutes. You’re on Portland time!

After you drop off bags at the Ace Hotel, the next step is to get a bike. There are several establishments offer rentals, from just $25 a day. You might as well get a little exercise in, because you will be eating a ton of food here.

Now that you have wheels, so to speak, it’s time to explore this lovely city. Next door to the Ace Hotel is Kenny and Zuke’s delicatessen, where you can grab a New York-style bagel or an overloaded Reuben sandwich. A few blocks over is Powell’s Books, taking up an entire city block and luring you into it’s dreamy rows of books.

Over on the Southeast side of town, ride along Hawthorne, stopping at the amazing House of Vintage. Further down the street, you’ll find a host of tiny consignment stores, coffee shops and the amazing Bagdad Theater, where you can order a Portland microbrew while catching an afternoon flick.

After an afternoon on Hawthorne, it’s time to find a snack. Pambiche, only a 10-minute bike ride north, is a tiny, brightly colored Cuban cafe, and their Happy Hour is no joke. Fresh fruit cocktails and small plates starting at $2.00. Order one of everything.

Following your food frenzy, a leisurely bike ride is in order. Pick a route, or simply ride along the Waterfront Park Trail on the West side of the Willamette River, passing by the area where the famous Saturday Market as held.

Portland nightlife is a reflection of Portland day life. Chill, relaxed and all about having a good time. Some of my favorite spots include Valentine’s for shows, Clyde Common for a great cocktail, Ground Kontrol for arcade games (a staple in every city, as far as I’m concerned!) and of course, The Tube, for a crazy fun night of dancing and general shenanigans.

There is also an almost unlimited supply of breweries located around downtown. Before you know it, you’re going to need a midnight snack. Cruise on over to one of the many Food Cart “pods” and enjoy pretty much any and all cuisine you can dream of. Check out this handy map!

Two words. Voodoo Doughnuts. Once you have had your fill of drinks and dancing and fried things, you need to experience this sugary bite of heaven. Doughnuts covered in Cap’n Crunch cereal! Doughnuts slathered in maple frosting and whole strips of bacon! The wonder of it all!

If you are still alive the next morning, it’s time for brunch. Pine State Biscuits over in Northeast or Bertie Lou’s over in Southeast. Or you could just eat another Doughnut and call it a day.

Eat. Sleep. Bike. Portland Style. Read more and keep up with Celessa over at TheEverydayJumpseater.blogspot.com!


Celessa Lynn
writer // dreamer // adventurer // flight attendant

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