Weekend: Portland, Oregon

Playing tourist in my own city for a weekend in Portland is always a good time—it’s the perfect way to stumble upon new spots or fall back in love with old favorites. After a few challenging years, it’s been exciting to see Portland bouncing back with vibrant energy, creative spaces, and lots to explore (fair warning: this is a long list of personal faves).

While summer is arguably the best time to visit Portland—with long, dry days perfect for patio hangs—spring bursts with color, and fall has its own crisp, golden charm. As for winter? I usually make a run for the sun, but if cozy, rainy vibes are your thing, you might just love it.

Looking for even more tips for a weekend in Portland? Read up in my other post about breweries, rooftops, and happy hours or go a little further afield with a few great day trips (or weekend excursions…).

Getting There

Portland’s airport (PDX) is one of my favorites and with the recent opening of its new terminal is even better—in fact, The Washington Post ranks it as the best airport in the U.S.! PDX is close to town and downtown Portland is easy and inexpensive to get to from the airport via public transit (more on that in a moment). The airport is small enough to be pretty easy to navigate and Portland rarely has the type of weather that wreaks havoc with delays and cancellations some major hubs experience (ahem, Chicago, San Francisco, and New York). Still, it’s big enough to offer nonstop service to much of the U.S. as well as a growing number of international destinations.

PDX has Alaska, Delta, and United lounges that are fine, if not special (although I do love the staff at the Alaska Lounge). There’s also a just-opened in 2025 Escape Lounge (which welcomes Priority Pass) that looks pretty swanky from the entry and pictures, though I haven’t yet seen inside in person.

Once at PDX, I find it really easy to get into Portland and back. Our local transit system, TriMet, is relatively inexpensive ($2.80 one-way, or $5.60 max per day, with no additional fees to/from the airport). It’s reliable, and its trains and busses provide ready access all throughout the city just by tapping your credit card or buying a reloadable Hop card.

Know Before You Go

Look, Portland got some really bad press in and after 2020. Some of it was deserved, some of it I felt was overblown, and most of it made it sound like the entire city was about to implode. In reality, the worst of the issues were contained to a just a few blocks in downtown. Fortunately, we’ve been on the mend for a few years now, and while I’ll acknowledge we don’t have it all figured out yet, things are much better.

Homelessness, in particular, is something that Portland—as well as many cities, especially on the West Coast—continues to struggle with, although things are slowly improving. I’ll editorialize to say Portland can get in its own way debating a perfect solution, rather than sustaining a focused effort on improvement. But in the end, the folks struggling on the street are still human and I hope they obtain the help they need just as I hope the fear of Portland’s issues won’t keep good people from visiting what is a great city. With only a few exceptions, most of the city is still a great place to explore.

LGBTQ Safety

Gayety lists Portland as the best city in the U.S. for same-sex couples, for what that’s worth. The city also scores a perfect 100 in the Human Rights Campaign database of LGBTQ protections and has a large number of LGTBQ focused organizations. Oregon earns a C grade from Safehome.org for LGBTQ safety—their rating is a mix of legal protections and reported hate crime statistics (the data available to them and the fact that it’s statewide mean the ranking is imperfect, but few other resources include hate crime statistics in their formulas). On the other hand, Oregon is listed as one of the safer states in terms of transgender protections and a relative lack of anti-trans legislation.

While Portland is generally very safe for LGBTQ folks, the state’s C grade seems fair enough—I wouldn’t consider it unsafe, but I’m certainly more vigilant when I’m outside Portland.

Walking around Portland over the weekends or during the week, I’ve felt safe, and displays of affection are common enough in and around urban spaces and LGBTQ events. Every once in a while, some type of anti-LGBTQ rhetoric pops up, so as with anywhere, be mindful of your surroundings wherever you go.

Sightseeing Highlights

A weekend in Portland can be a paradise for urban hikers, foodies, beer and wine snobs, coffee fanatics, cocktail aficionados, and all sorts of other folks. My list of highlights below is hardly exhaustive, but I’ve tried to focus on either personal favorites or things that are less likely to be mentioned elsewhere.

• The four t’s of the 4T Trail are: trail, tram, trolley, and train and refer to a really awesome loop through Northwest, Southwest, and South Portland. You can easily do all or part of the 4 t’s, the trail hike from Forest Park to Marquam Hill, the aerial tram ride from Marquam Hill to the South Waterfront, the streetcar (trolley) to downtown, and MAX light rail (train) back to Forest Park. Note that TriMet’s HOP fare payment works on both the Portland Streetcar and MAX light rail (as well as TriMet busses), but the fare for the aerial tram must be purchased separately. See below for additional details about the tram.
• The Portland Aerial Tram from the South Waterfront to Marquam Hill is a fantastic way to get panoramic views of the city, even if you don’t do any of the other parts of the 4T Trail. It’s an $8.50 round trip ticket and while there’s not much to do at the top of the hill if you aren’t setting out on a hike, it’s still beautiful. Note that the tram doesn’t run with the frequency of other transit including being closed on Sundays and holidays, as well as Saturdays after 5pm.
• Tilikum Crossing Bridge is also on my unintentionally transit-focused list, but was the first major bridge in the U.S. designed to allow access to transit vehicles, cyclists and pedestrians but not cars. It’s a pretty walk (or ride) from the South Waterfront side to Portland’s east side, including to Oregon’s Museum of Science and Industry (OMSI). At night, the bridge’s lights double as an art installation, changing color based on water depth, speed, and temperature.

There’s plenty to do in Portland that isn’t specifically transit focused, too. Finding public art is one way I enjoy exploring different parts of a city, and Portland is full of great opportunity for art exploration.

• Lee Kelly’s massive metal sculptures are found throughout Portland, from the South Waterfront to the VA Medical Center on Marquam Hill to the International Rose Test Garden and beyond. Portland Art Museum hosted an exhibit a few years ago, and created a walking tour map and it’s a great tool to cover some less-traveled parts of Portland (spoiler: it’s not all walkable from one to the next).
• The city also features a myriad of murals, including Attitude of Gratitude, one of my favorites near SE 10th Avenue and SE Division. Conveniently, the Cuban restaurant and cocktail bar Palomar is located here too, plus Pine State Biscuits and several other delicious spots just blocks away on Division near SE 12th and 13th Avenues.
• Kvinneakt, the bronze sculpture in downtown Portland of a naked woman may be one of Portland’s most well-known pieces thanks to former Mayor Bud Clark’s “Expose Yourself to Art” poster (the poster was created several years prior to his election as Mayor). There are many other sculptures in the nearby blocks surrounding Portland’s Pioneer Courthouse Square.

You may have heard, but Portland is also a coffee town. For the most part, Portland does its coffee thing on a smaller scale than our neighbor to the north, Seattle. But in this case, it’s a good thing. Besides simply grabbing a delicious brew from a local roaster, there are some great next-level experiences too:

• Third Wave Coffee Tours is run by owner/guide Lora Woodruff (she has a few other guides now too). I’ve been on multiple tours of hers and have recommended her to many other people. Not only do her tours provide a diverse sample of Portland’s coffee scene, but she also shares a fascinating amount of information about coffee growing, production, and styles.
• The coffee fun isn’t all reserved for tours, though. If you’ve never been to a cupping, several Portland-area roasters offer them and it’s a great way to learn more about your brew. While the Wikipedia description of cupping focuses on “the practice of observing the tastes and aromas of brewed coffee,” the roasters I’ve joined in Portland often include details with the whole and ground beans as well. Try a free cupping at Coava; other roasters may also offer them from time to time so if you find yourself in one of Portland’s roasters or small coffee shops, it’s worth an ask.
• Or you could pick up skills to be a home barista. Clive Coffee offers classes not only focused on the home barista, but also teaches latte art! If you’re spending a little more time (or you’re a Portland local), Portland Community College offers coffee roasting and tasting classes as well.

If April showers bring May flowers, just imagine what Portland’s long, wet winter brings! Spoiler: it brings magnificent green spring and summer months, lots of beautiful blooms, as well as striking fall color. A very short list of some prime spots to check it all out include:

• I consider the Portland Japanese Garden as one of the most beautiful and serene places in the city, and I think many other folks share that sentiment. The zen garden, ponds, streams, manicured grounds, and rotating exhibits all come together beautifully. Fall color is especially striking here, but it’s beautiful year-round.
• As celebrated as the Japanese Garden is, the Lan Su Chinese Garden is equally wonderful. The Old Town/Chinatown location was pretty dodgy a few years ago, and you’ll still see remnants of that, but once you’re inside the sculpted walls of the garden, you’d never know the difference. As a bonus, the tea room inside the garden is a welcoming spot to relax and drink up your surroundings, literally.
• For something different, the Crystal Springs Rhododendron Garden is a city park in Southeast Portland that’s a stunner when the rhododendrons and azaleas are in bloom. The first weekend in April is the garden’s annual show, and Mother’s Day weekend typically is a great viewing time as well.
• While the Japanese, Chinese, and Rhododendron Gardens require paid admission, Portland—the Rose City—has two different, but equally beautiful rose gardens. The International Rose Test Garden is in Washington Park, prominently features a Lee Kelly sculpture, and is just a few steps from the entrance of the Japanese Garden. From late-spring (Portland Rose Festival is in May) through summer, it’s bursting with some of the most beautiful, unusual, and fragrant blooms you’ve seen. Alternately, the Peninsula Park Rose Garden is less well-known, but equally lovely and usually less busy.

While it doesn’t fit in any of the categories above, Powell’s City of Books is a Portland landmark and a destination in itself. Not only is it proclaimed as the world’s largest independent bookstore, it’s a cultural and people-watching experience. It’s worth the time, whether you’re an avid reader or not.

Portland has an eclectic drag scene with a wealth of evening shows and drag brunches. But if there’s one spot to prioritize on your itinerary, it’s Darcelle’s. This is the legendary home of Darcelle XV (Walter Cole), the oldest performing drag queen prior to his death in 2023 at the age of 92. The show continues on with weekend brunches as well as evening shows.

As well, check out a number of other guides, including Willamette Week’s how to do the most while spending the least (double check things ahead of time though, some are seasonal).

Eating and Drinking

My two cents: Portland deserves its reputation for being a food destination. We’ve got a great variety of fantastic food, generally without the pretense or expense of other cities known for their food culture. I’ll caveat my praise for Portland dining by noting that we don’t always nail the exceptional service of more established destinations like San Francisco or New York. But there’s still a lot worth checking out!

Top Chef fans will find a lot to explore here. Portland is home to several contestants and finalists, as well as hosting the 18th season of the show, which aired in 2021. If you’re doing the Top Chef tour of Portland, here’s are a number of spots for your list:

• Gregory Gourdet, runner up for Top Chef Season 12 in Boston and a finalist in All Stars LA, opened the Haitian-focused restaurant Kann in 2022 (a block from my office in SE Portland). As you’d expect for a restaurant lauded as the James Beard Foundation Best New Restaurant in 2023, be sure to make reservations well ahead of time, tables at Kann are booked up several weeks to months in advance.
• Gabriel Pascuzzi, Season 18 contestant, also has restaurants in Portland. Things change quickly, though. The day before I published this post, his Mama Bird restaurant in NW Portland closed. He’s since reopened (on February 7) as Bistecca, a food fired steakhouse. As far as I know, the NW Portland location of his Feel Good casual bowl restaurant is still open.
• Doug Adams landed as a top 3 finalist in Top Chef Boston, right behind Gregory Gourdet and is now chef/owner of Grand Fir Brewing in SE Portland (he presided at a couple other spots before handing here). The food is very good and the beers are pretty solid too.
• During Season 18, the chefs made a stop at Portland Mercado, which is an awesome market, food cart pod, and business incubator space in SE Portland, and generally a celebration of Latino culture. While some of the carts change from time to time, I recommend getting a bite of Colombian food from Que Bacano (they also have a brick and mortar location on SE Hawthorne, both owned by the brother of a friend and former co-worker).
• Akadi, which Season 18 contestants visited in Episode 3, is chef-owner Fatou Ouattara’s West African restaurant. Ouattara is known for her attieke poisson (grilled whole fish with grated, fermented cassava) and peanut butter mafe and shosho (black eyed pea stew).
• Departure gets an honorable mention since it’s where Gregory Gourdet was Executive Chef until 2019. It’s still a wonderful place to go, especially on a summer day when you can enjoy the rooftop patio with views of the city, Mt. Hood, and the Willamette River.

The city is also well known for its food cart pods, including Portland Mercado mentioned above. My top two picks are:

• Prost Marketplace is on N. Mississippi Avenue and Skidmore. This collection of carts surrounds Prost, a German-themed pub and taproom. And if you’re not up for a German beer, there’s a cocktail bar that’s part of the pod. I’ve not had anything here I haven’t liked, though the barbecue is especially good. Koi Fusion’s burritos used to be among my favorites, but I think their quality has slipped of late.
• Hawthorne Asylum, on between SE Hawthorne and Morrison, has another great collection of food trucks (and drinks), with lots of places to sit and enjoy whatever your belly fancies. They turn on the heat lamps and fire ring in cooler weather, so it’s a decent option even if the weather isn’t perfect.
• Pine Street Market isn’t a cart pod, but until the long-promised James Beard Public Market actually opens, Pine Street is Portland’s answer to the food halls such as those in Europe. It’s definitely smaller and less vibrant than food halls elsewhere, but does have a good collection of vendors cooking up a variety of global foods.

Portlanders probably won’t be surprised to read this, but others might. The city has some great southern food, such as:

• Screen Door is certainly one of my favorites, and as anyone who has been there knows, the fried chicken and waffle plate is enough to feed a small army. Grits, benedicts, hashes, and everything else I’ve eaten there are also delicious. In addition to their original location on East Burnside, there’s a newer location in the Pearl District that’s very different aesthetically, but just as yummy, and now an outpost in PDX Airport’s B Concourse. Reservations are only available for larger groups at the two in-town restaurants, so go early or prepare to wait a bit.
• Gravy, on North Mississippi, has a more casual dining room than Screen Door, but equally good food. It’s particularly busy for weekend breakfasts (and also doesn’t take reservations).
• Miss Delta, across Mississippi street, is another good spot, especially if you’re not willing to bear the wait at Gravy. Whereas my menu selections at Gravy have generally been of the comfort food variety, Miss Delta leans into barbecue offerings, and I’ve loved everything I’ve ordered there too.

I have a few other favorites that didn’t quite fit in other categories, but they definitely deserved mention, so I didn’t want to leave out altogether. Those include:

• Mother’s Bistro in downtown Portland has been around for decades, although only a few years in its current location. I can’t recall being in the restaurant when chef/owner Lisa Schroeder hasn’t been there. She’s got a fun amount of sass and is charming (she always pretends she knows the hubby and I when we introduce ourselves, though I can’t imagine she could remember us among all the folks who really do know her). While other meals are very good at Mother’s, brunch—especially the salmon hash and one of their bloody Mary’s—is my favorite, but it’s also the busiest.
• Nong’s Khao Man Gai in SE Portland (a block from Kann, for what that’s worth) is known for their seemingly simple dish of chicken, tofu or vegetables plus rice. But the whole is so much greater than its parts. Order a plate at their walk-up counter, then take a seat at one of the tables inside or out. It comes with a broth and peanut sauce that are unique and delicious and also somehow defy better description. There’s also a decent ramen place next door if you’re with others and want to try a variety of things while you’re here.
• Allora, at the edge of the Pearl District, is another favorite. Their simple but delicious Italian dishes are ones I keep coming back to, and their staff is friendly and attentive (something that Portland doesn’t always do as well at as it should).
• Tulip Shop Tavern on NE Killingsworth is definitely not a tulip shop, but it’s a mighty good tavern. They have a creative drink menu and a short tap list, but the real (and unexpected if you haven’t been here) draw is their menu. It’s tavern food prepared really, really well.

Portland is also well-known for its micro- and craft breweries. Regardless of what neighborhood you’re in, it’s easy in Portland to find a local brewery. Check out my separate beer and happy hour post. Or, check out lists from Travel Portland and Eater PDX.

If you’re looking for drinks but have tapped out on beer, Portland will still keep your whistle wet. There are plenty of bars (of the fancy kind and the dive kind) that’ll mix up an amazing drink and a few places with good happy hours listed below, but Portland’s Distillery Row (check out the Distillery Passport, too) and small urban wineries are some other options that might also help you explore Portland and also find something new and local.

If you’re still looking for more ideas, check out Travel Portland’s guide to dive bars (I’ve been to most of these and can vouch for the list) or Eater’s list of the best cocktail bars (I’ve been to about half of their list and would agree that they’ve assembled a good collection of spots as well).

Nightlife

While Portland isn’t really a 24/7 city, there are often happenings in the evening and at night. So a weekend in Portland, particularly in the summer and/or on the weekends will be full of opportunities. Venues like Alberta Street Pub, the Doug Fir Lounge and the Crystal Ballroom get a mix of musical and other talent. And monthly events such as First Thursday in the Pearl District or Last Thursday on Alberta Street bring a little extra life to the streets in these neighborhoods.

As for LGBTQ nightlife, I find Portland to be a bit sleepier than one might assume based on its per-capital population of LGBTQ folks, but there are a number of spots to imbibe, dance, people-watch, or stand and model.

• Badlands is Portland’s newest venue, and I’d argue it’s probably the nicest. Opened in 2024 and owned by the same folks as Badlands in San Francisco and Sacramento, it also feels pretty similar inside. It’s clean and fun (I think), have efficient staff and some happy hour deals, and a relatively mixed crowd for Portland.
• Scandals might be the stalwart in town if Badlands is the new kid on the block. It’s the place where I’m probably most likely to run into folks I know and it’s the last gay bar remaining on what was known affectionately (I think) as Vaseline Alley. I wish Scandals would put just a tiny bit of effort into stepping up their aesthetic game, but it can be a fun place if the crowd is decent.
• Silverado and Stag are just a block or two from Badlands and are walking distance from Scandals and are Portland’s two gay stripper bars. Portland has more strip clubs per capita than anywhere else in the United States, so it tracks that we should have a couple gay ones too. Silverado is a bit seedier but has great drink specials earlier in the night (usually before the strippers take to what Silverado generously calls a stage). Stag is nicer, but gets much more of the bachelorette-type crowd who often don’t care much about respecting the space they’re in.
• In the Old Town Neighborhood, there’s also CC Slaughters (which also has a location in Puerto Vallarta). Last time I was at CC’s, they had a younger crowd than the places mentioned above and it was fine, but not really my vibe. I’ve heard it’s not as busy now that Badlands is open nearby, but feel free to judge for yourself.
• Finally (at least for my list) there’s Eagle Portland, which unfortunately isn’t located anywhere near the other places. It’s not that the Eagle is in a bad neighborhood, it’s just that it’s either your destination or it isn’t because there’s little else near it to hop to before or afterwards. Inside, it’s about what you’d expect for a gay bar named the Eagle. I’ve been there enough that several of the staff recognize me (sorry, Mom), so I think they’re a friendly bunch. Check out their Facebook or Instagram page before going if knowing what the night’s theme is before arriving.

Lodging

Portland has lots of choices for places to stay, spread across most of the neighborhoods in the city. The Pearl, downtown, and Lloyd/Convention Center areas are most easily accessible by transit, but there are plenty of other options too. A few of my top suggestions (almost all of which friends or family have stayed in) include:

• The Portland Hilton on SW 6th between Salmon and Taylor is also adjacent to Hilton’s boutique(ish) Duniway Hotel. Both hotels are nice and have been redone in the past several years (though the Hilton still has smallish, old-school rooms) and have decent restaurants on the ground floor.
• The Nines in downtown Portland is in the former Meier and Frank department store building (follow the link for some fun architectural history) and is one of Marriott’s Luxury Collection properties. The rooms are nice and the top floor is Departure Restaurant, mentioned above.
• The Hampton Inn in the Pearl District is relatively new. It’s probably the nicest and most modern Hampton Inns I’ve ever seen. It also has a lovely rooftop patio (where the hubby and I got married, for what that’s worth). Sadly, the ground floor restaurant seems to have lacked staying power (thanks COVID) so on site dining might be limited to the typical uninspired free breakfast, but there are plenty of other options nearby.
• The Inn at Northrop Station is a good option if you want to get out of downtown a bit, but still want easy transit access. The rooms are quaint and spacious (many with kitchenettes is that’s of interest), there’s parking if you have a car, and there’s a nice second floor patio to relax on.
• Then there’s the Vancouver AC Hotel by Marriott. It’s not technically in Portland, but Vancouver’s waterfront is about as close as you can get without being in the city. The newly developed riverfront where it’s located is awesome (and is on the flight path for PDX, if that’s of interest), and it has a wonderful roof deck. Depending on what adventures you have planned, Uber/Lyft rides might be cheaper than parking, but otherwise the location is awesome.
• A few other Hilton options include the Canopy in the Pearl, Doubletree at Lloyd Center, and a handful of spots at PDX Airport, most with shuttles to the terminal, and a few close to MAX light rail for trips into town.
• Other Marriott options include the downtown Courtyard in the Pearl (which may or may not have a ground floor restaurant; it’s suffered the same challenges as the Hampton), another Courtyard on the other side of the river, the Hi-Lo Hotel (with a very good restaurant/bar) the Marriott Downtown Waterfront, downtown Moxy, and others.
• For something totally different, there’s the Northwest Portland Hostel, recently named the best hostel in the U.S. While I haven’t stayed there and can’t vouch for the accommodations, I can vouch for the location, which is great: easily walkable to areas of NW Portland and the Pearl, Providence Park for Timbers/Thorns games and concerts, and to the MAX Red Line to/from the airport.
• And some other marginally/potentially less corporate options include (on the west side of the river) the historic Heathman Hotel, Kimpton’s Hotel Vintage or Riverplace Hotel, or Hotel Zags. On the east side of the Willamette River, there’s the Jupiter Hotel (and Jupiter NEXT), the Hotel Kex, and the Hotel Eastlund (see above for their rooftop happy hour).