Portland is a city full of eclectic charm and plenty to see and do—even on a three-day weekend stay. From nature walks to downtown strolls; top-notch hotels, restaurants, and boutiques; an arts district that wows; a cup (or two!) of delicious coffee, and everything in between, this hip Oregon city is a paradise for visitors who want a weekend getaway to remember.

Note: the following itinerary is designed for a 72-hour getaway to Portland, but can easily be adapted to fit into a short weekend stay, too.


Other Helpful Info: Masks are currently required for all people in indoor spaces in the state of Oregon, regardless of vaccination status; and as of August 27, 2021, masks will also be required in most outdoor settings. Proof of vaccination may also be required for entry into restaurants. Always check the latest state and local COVID-19 protocols before traveling.

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Walkable Portland

Portland is an extremely walkable city, so be prepared to get out and stretch those legs! It’s divided up into several neighborhoods that each have their own attractions and unique charm; offering travelers a hodgepodge of fun things to experience while getting a taste of Portland’s many highlights. Portland also has an efficient transit system (known as TriMet) that includes buses, a light rail, and a commuter rail. Learn more about the city’s public transit including schedules, rates, and trip planners, by visiting their website.

Planning Ahead: Where To Stay In Portland

There are many cool accommodations throughout the city—each with its own special charm and proximity to many of the city’s diverse attractions. Below are a few top places to stay when hitting Portland for a long weekend.

  • The Jupiter Next Hotel is on the Eastside of Portland and has easy access to the downtown area
  • The Inn at Northrup Station is a great place to stay in the city’s Nob Hill neighborhood, as it's close to a ton of things to do within walking distance
  • The Hoxton is located in the Burnside neighborhood in the heart of downtown, giving travelers easy access to all of Portland’s best attractions

Day One: Arrive In Portland

The first day on the itinerary is by far the most laidback—however it does offer visitors a chance to explore their surroundings while getting a feel for the city.

Explore The Neighborhood

No matter where you stay in Portland, there’s always something fun to check out. Here are the best ways to spend your first few hours in the city.

  • Arriving in the morning? Then start the day right with a cup of coffee at Courier Coffee, located in downtown Portland
  • Later arrivals will want to grab lunch at il Solito a cozy downtown spot located in the Kimpton Hotel Vintage Portland
  • Explore Powell’s City of Books, the flagship store of the world’s largest chain of independent bookstores
  • Head to the cobblestone streets of the Pearl District to browse the area’s chic boutiques, such as Garnish Apparel, then head to the Low Brow Lounge for a low key dinner and a pint

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Day Two: A Fun-Packed Saturday Checking Out The Best Of Portland

Start the day with a quick on-the-go breakfast and cup of coffee before heading out to explore. Today is the day to check out the best of Portland’s most walkable neighborhoods—dig the scenery, explore the culture, and eat and drink 'til your heart’s content on the first full day in the city.

  • Take a hike up to Pittock Mansion and see the views from Forest Park and the International Rose Test Garden
  • Head to the PSU Farmer’s Market open Saturdays year-round. Stop at one of the fantastic food stalls to grab lunch
  • Explore Portland’s art scene by spending the afternoon at the Portland Art Museum, then checking out the outdoor art installations in Pioneer Courthouse Square
  • Sip a Happy Hour whiskey at Pope House Bourbon Lounge, then head to Portland institution Jake’s Famous Crawfish for a late dinner

Day Three: Outdoor Adventure + Amazing Art = A Winning Combination

Travelers can make the most of their last full day in Portland by taking in some of the city’s best scenic sights; exploring the famed Arts District, and ending the day with a fab dinner.

  • Take a hike on Mt. Tabor’s easy, flat loop for some stellar views of downtown; or head out to Powell Butte to catch the best views of Mt. Hood and Mt. St. Helens.
  • Head to the bustling Alberta Arts District and have lunch at one of the city’s famous food carts. Mississippi Avenue is known for having some of the best in the city, like local fave Matt’s BBQ
  • Hop on a bike or electric scooter and spend the afternoon exploring the Arts District’s outdoor murals, hip boutiques, and live events. Or spend the afternoon taking in a show at The Alberta Rose Theater
  • Nosh on Burmese-inspired delish dishes at Expatriate, or share some Spanish tapas at Urdaneta. The Portland food scene is so diverse, it has something for everyone!

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Day Four (Optional): Day Trip To Columbia River Gorge

For travelers fortunate enough to have another day in Portland—kudos to you! The perfect thing to do on an extra day in this amazing city is to take a day trip to the Columbia River Gorge. Be sure and check out the beautiful Multnomah Falls on the way! Here’s some info on taking a day trip from Portland to Columbia River Gorge.

Portland is a bustling, eclectic city with plenty to see and do to suit the fancy of any traveler—from outdoor enthusiasts to art lovers; discerning foodies, bibliophiles, savvy shoppers, and everything in between. So make the most of 72-hours in Portland by neighborhood hopping and getting a taste of all this amazing city has to offer.

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