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How to spend a weekend in Portland, Oregon

Willamette River

When people ask me how long to spend in my home city of Portland, my answer is always four to five days. While Portland isn’t huge, there’s so much to do in the surrounding areas, giving it tons of day-trip potential. Of course, you don’t always have four or five days to spend, and if that’s your situation, this itinerary is for you. I’ve narrowed it down to just the highlights (and kept it almost exclusively within city limits!) so that you can make the most of the time you do have. So without further ado, here’s how to spend a weekend in Portland!


Mt. Tabor view
Forest sunset



Welcome to Portland! After settling in to your hotel (I have plenty of recommendations over in this guide), head over to the southeast portion of the city to enjoy two things Portland is known for: views and wine. Many local wine shops offer tastings on Friday evenings, and since you might not have time to get over to the Willamette Valley on this trip, this is the perfect way to sample the region’s famous pinot noir. I particularly like the “Friday Flights” at Vino, which go from 4:30 until 8:00 and offer a flight of five wines for $10.

If you’re visiting in the winter months when days are shorter (and if it’s not raining outside!), you may want to catch the sunset from Mt. Tabor before your wine excursion. This volcanic cindercone is home to a public park and lovely sunset views, as well as lots of trails. If you’re visiting when days are longer, though, you can get your wine in first and then head to Mt. Tabor afterward.

No matter what order you do them in, after those two activities are done, you’ll probably need dinner, and the good news is you’ll have great options close by. Sister restaurants Tusk (Mediterranean small plates) and Ava Gene’s (seasonal Italian) are each within 10 minutes from Mt. Tabor by car, and Tusk is a five-minute walk from Vino. 

Still up for more activity? Make your way back downtown toward your hotel for a nightcap—I love Abigail Hall, Pepe Le Moko and The Hoxton’s unnamed basement speakeasy, to name a few cocktail spots—or, if you really want to go all out and get a true “Portland” experience, head to Hale Pele, a tiki bar like none you’ve ever seen (and a guaranteed good time).  




You’re in Portland, so you should probably grab some of the coffee this place is famous for to start off your day. I really like Good Coffee and Coava Coffee, both of which have locations downtown (though if you want to hit up the regional classic Stumptown instead, no one will judge). If you choose to take it to go, you can enjoy it while strolling through the Portland Saturday Market, which affords fantastic riverfront views.

Dedicated bruncher? If you don’t mind backtracking a bit and didn’t visit Tusk yesterday, it has a stellar brunch menu, and you can really appreciate its gorgeous interior in the daylight. But if you have what you need to start your day after your coffee stop, head out to what is perhaps Portland’s most famous attraction: The International Rose Test Garden. There, you’ll find a seemingly endless number of rose varieties (assuming it’s the time of year when they’re in bloom, of course!) and lots of beautiful views. To maximize your time in the area, consider adding on a visit to the Portland Japanese Garden as well.

Once back downtown, explore Powell’s City of Books, which sits in the heart of the city’s Pearl District. Only you can predict how long you’ll want in world’s largest independent bookstore, which inhabits an entire city block. For some, a quick pass-through is enough to get the idea, but if you’re bound to get lost in a few of the million-plus volumes inside Powell’s’ walls, allot some extra time!



If you skipped brunch and are in need of lunch at this point, try nearby French luncheonette Maurice for a sit-down option or Lardo (a sandwich spot) for something quicker. Just a little bit further away, Pine Street Market offers tons of different options. 

Depending on how much time you have left in the day, you may choose to check out one of Portland’s many breweries, browse the boutiques downtown (there are lots clustered in and around the Union Way shopping arcade) or head back over to the city’s southeastern quadrant to check out the vibrant thoroughfares of Hawthorne and/or Division. If you stay downtown, Tope is an excellent spot for a rooftop dinner of tacos and margaritas (especially in the summer!). Otherwise, try something different at Kachka, a spectacular restaurant serving modern Russian food.

Case Study Coffee cups
Case Study Coffee



In my opinion, you can’t leave Portland without getting up to the Alberta Arts District, a stretch of NE Alberta chock-full of street art, quirky shops, restaurants and more. This is definitely a more “Portlandia” area of the city thanks to its relaxed vibe and plethora of independent businesses, so lean in by dropping into a vegan bakery, browsing at a record store or stopping for a locally made kombucha. If you need a pick-me-up along the way, try Case Study Coffee.

For a trendier dining experience, Australian cafe Proud Mary is a favorite of mine for brunch. Go as early as you can, as it can get packed (but on the flip side, don’t worry too much if there’s a wait, as turnover is often pretty quick!).

Multnomah Falls
Angels Rest


If you’re not taking off until late Sunday or early Monday, take the afternoon to get into nature. Portland is so close to so much of it, making it an outdoors lover’s paradise. 

If you have access to a car, you can’t beat the views in the Columbia River Gorge, beginning just 20-30 minutes outside of the city. With limited time, plug  Multnomah Falls into your GPS and marvel at the water (from underground springs!) cascading down the side of the mountain behind the famous footbridge. If you have a few hours in the gorge and enjoy hiking, Angels Rest is a great moderate hike you can do to enjoy panoramic views, and you can easily stop at the falls before or after. Got most of the day to kill? Hood River is a great post-hike town full of eateries and breweries (and it’s close to pick-your-own fruit and flower farms, which offer a fun activity during the summer months). 

If you don’t have a car, don’t worry. 5,200-acre Forest Park is home to more than 80 miles of trails and roads, and it’s located within the city limits!

For more on Portland, check out my complete guide to the city and my day-trip guide. Need a longer itinerary for Portland that includes some of those day trips? I’ve got that right here! And for info on how to visit the city for free, check out the 52 Cities free resource library or register to join me on an upcoming masterclass!

Hope this itinerary is useful in planning your weekend in Portland! What are you most looking forward to doing? Let me know in the comments! >>

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How to spend a weekend in Portland
How to spend a weekend in Portland
How to spend a weekend in Portland







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