Traveling over the weekend to Portland, Oregon or Boulder, Colorado? We’ve got you covered!

Both of these cities are finalists in the CheapOair Owards’ Most Effortless City category—meaning they’re an absolute breeze to visit. Lucky you! This will be a seriously relaxing weekend.

Not sure what to do or where to eat? We’ve got it all figured out for you. Make sure you leave time to celebrate National Chocolate Milkshake Day on September 12th! Follow this cheat sheet over the weekend to make planning your getaway a bit more effortless.


If You’re Headed to Portland

What to do:

Josemaria Toscano / Shutterstock

Josemaria Toscano / Shutterstock

People’s History of Portland Free Walking Tour

This walking tour highlights the immigrants and working class of Portland, who were at the helm of the city’s social activist movements. The tour offers the story of Portland to tourists from the point of view of the people who made the city what it is—but are often left out of the conversation.

Oregon Historical Society Museum

The Oregon Historical Society Museum is housed at the Oregon Historical Society in downtown Portland, and it’s filled with cool artifacts and memorabilia. Ever seen a Portland Penny? That’s how this city got its name, and you can cross it off your bucket list right here!

Where to eat:

"Voodoo Doughnuts" by Nathanael Burton is licensed under CC 2.0.

Voodoo Doughnuts” by Nathanael Burton is licensed under CC 2.0.

Cool Moon Ice Cream

This coffee bar and parlor, which serves all-natural ice cream, is the perfect place to celebrate National Chocolate Milkshake day while you’re in Portland. Anything is a safe bet, but try the Mexican Chocolate Shake for a spicy-sweet treat!

Voodoo Doughnut

If you’re craving something sweet after midnight, head on over to Voodoo Doughnut, where you can indulge in unique doughnut offerings such as the Bacon Maple Bar doughnut or Voodoo Doll doughnut.

If you’re headed to Boulder

What to do:

Pell Studio / Shutterstock

Pell Studio / Shutterstock

CU Buffs vs. Massachusetts at Folsom Field

Love college football? You’re in luck! Head over to Folsom Field to cheer on the Buffs as they take on Massachusetts. You can even pretend you’re in college again with a good pre-game tailgating party. Grab some tickets for the game here.

Boulder Museum of Contemporary Art

Love art, but hate spending money on museum tickets? PROBLEM SOLVED. You can get into the Boulder Museum of Contemporary Art for $1 and explore current pieces of art from the region. Perfect!

Where to eat:

Alena Haurylik / Shutterstock

Alena Haurylik / Shutterstock


After your hike – or the football game – grab a black angus beef burger from Larkburger. This restaurant, known for its truffle fries, is located in the heart of Boulder.

Boulder Baked

Swing by Boulder Baked to try a Nutella Chocolate Chip cookie, the cookie of the month, along with your choice of a milkshake. Alternatively, you can just get some milk on the side, but really, you should live a little.

Are you headed to Boulder or Portland this weekend? #Bestweekendever, am I right? Let us know in the comments! And of course, don’t forget to vote for your favorite city in the Owards contest!

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About The Author

Hannah Winsten is a freelance writer and marketing consultant living in New York City. A total travel junkie, Hannah came to CheapOair as a French translator and SEM associate after returning from a stint living abroad in Paris. She’s also working on her first book--you know you want to read it. Find her on Twitter at @HannahRWinsten.