Humans love categorizing. We recognize patterns, and when it comes to wine, we love to put regions in neat little boxes. Tuscany grows Sangiovese; Rioja grows Tempranillo. In the United States, California is known for its Cabernets, and Oregon for Pinot Noir and Chardonnay. In fact, grapes grown in this region are incredibly diverse, with much of the experimentation happening in the Willamette and Columbia Valleys — a short drive away from the city of Portland.

If you have only 36 hours to spend in Portland, you’ll have a whirlwind adventure, tasting Pinot Gris, Trousseau, Sauvignon Blanc, Muscat, Riesling, Cabernet Franc, and yes, Pinot Noir and Chardonnay. Wine tasting around Portland will take you by gorgeous waterfalls and bucolic hills, as well as regionally inspired restaurants and cozy wine bars. The Portland area is more than the quirks it’s known for — restaurants and bars source from local farms, and art is a pillar of the community. With a whole weekend to explore, you’ll have time to soak in the locavore vibes — wine included.

Where to Stay

McMenamins Kennedy School

The McMenamins Kennedy School is one of the best places to stay for a weekend visit to Portland, Oregon.
Credit: McMenamins Kennedy School

The name of this hotel is not a play on words — The Kennedy School used to be an elementary school in Portland’s northeastern neighborhood of Concordia. The hotel celebrates its history, keeping the original structure, including the school’s original chalkboards in the rooms themselves, and adding literary-inspired decoration and design. You’re not here for the chalkboards, though. You’re here for the tile-lined, saltwater soaking pool, surrounded by luscious tropical plants. Grab a drink from the bar and chat with a local by the pool — it’s a classic Portlander hangout.

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If soaking isn’t your thing, sink into an armchair with a glass of wine while catching a movie at the hotel’s unique movie theater, lined with murals depicting the neighborhood and former school. When you’re ready to explore, you’ll be a short walk from bustling Alberta Street, lined with excellent coffee, restaurant, and bar options like dog-friendly brunch spot Tin Shed, vegan-friendly The Bye and Bye, and highbrow coffee shop Barista.

The Jupiter Original

The Jupiter Original is one of the best places to stay during a weekend trip to Portland, Oregon.
Credit: Jupiter Hotel

If your ideal getaway includes dancing the night away at the local music venue, you can stop scrolling through Expedia now. The Jupiter Hotel, attached to the well-loved Doug Fir Lounge, where this writer has had more than their share of late night tipsy dance-athons, hosts both global and local artists of all genres. If you’re a light sleeper, a room facing away from the venue might be your best bet. The Jupiter’s post-Covid reopening means newly renovated rooms with a focus on music — portraits of David Bowie, Nina Simone, and other greats line the walls.

The Jupiter’s “Fantasty Kits” exude the quirk Portland is known and loved for. If you’re coming from a state where cannabis isn’t yet legal for recreational use, The Jupiter’s “Everything But The Weed Kit” encourages you to check out the scene with a discount to the Oregrown dispensary, rolling papers, a stash jar, and a vape battery. The “SheBop Explorer Kit” includes a discount to everyone’s favorite local sex toy shop, SheBop, complete with a vibrator, lube sampler pack, feather tickler wand, and more.

Sentinel Hotel

The Sentinel Hotel is one of the best places to stay during a weekend trip to Portland, Oregon.
Credit: The Sentinel Hotel

The Sentinel is a part of Portland history. The original space was built in 1909 as the Seward Hotel, then became the Governor Hotel when it joined with the Elk’s Lodge next door. In 1985, the Governor was added to the National Register of Historic Places. After a renovation and restoration of the space, the Sentinel opened in 2012, keeping much of the standout Italian Renaissance architecture the building is known for. Look up when walking into the grand lobby, and you’ll notice some of the intricate carving on the ceiling harking back to its early 1900s build.

Local art lines the walls of the guest rooms, which range from cozy at 230 square feet with all the necessities to grandiose with a patio and outdoor fire pit. The gym is complete with Peloton bikes, and a wine lounge serves Willamette Valley specials. For the traveler with an eye for quality vintage luxury, the Sentinel delivers.

What to Do

Exploring the Columbia River Gorge

Exploring the Columbia River Gorge is one of the best things to do on a weekend trip to Portland, Oregon.

A visit to Portland without exploring the city’s natural surroundings is a visit wasted. Portland is centered in the gorgeous natural setting of the Pacific Northwest, a land of free-flowing rivers, mountains, and rainforest-esque parks. Get a permit to drive up to the mighty Multnomah Falls and Horsetail Falls in the Columbia River Gorge’s Waterfall Corridor, two must-sees of the region. Permit-free Wahclella Falls and The Vista House are in the area, too. On the way back, make sure to go through Cascade Locks to the Bridge of the Gods, which will bring you back to Portland on the Washington side. Local tip: Park at the historical marker to the right of the bridge for some excellent bald eagle viewing. I’ve seen one every time I’ve been there.

It’s no secret Portland is very LGBTQIA+ friendly. Columbia River’s Rooster Rock State Park, along with trails and disc-golf courses, has a clothing-optional beach often frequented by the queer community. The water is mostly shallow and cool, and the vibes are respectful and laid-back.

Portland Saturday Market and PSU Farmers Market

The Portland Saturday Market and the PSU Farmers Market are two of the best things to do during a weekend visit to Portland, Oregon.
Credit: Portland Farmers Market

A Saturday in Portland is not complete without stopping at one of two major markets. The Portland Farmers Market is held in the Park Blocks lining the gorgeous Portland State University campus, surrounded by beautiful elm trees. The market boasts over 130 vendors ranging from local farms to coffee, food, and craft offerings. It’s a delightful attack on the senses and an excellent way to get a feel for local agriculture. You’re liable to find everything from blackberries and marionberries to kimchis and kombuchas — locally made, of course.

Grab a snack and take the 28-minute walk, or 7-minute drive, to Old Town’s Portland Saturday Market on the waterfront, where you’ll find over 150 vendors showcasing handmade art, clothing, jewelry, furniture, and more. Hula hoopers, poi spinners, musicians, and other buskers regularly line the area, and the nearby park is the perfect place to pause and regroup.

Portland Art Museum

The Portland Art Museum is one of the best things to do during a weekend visit to Portland, Oregon.
Credit: Portland Art Museum

The Portland Art Museum is a seminal visit when you’re in the city. Located in the SW Park Blocks, it’s just a short stroll away from the PSU Farmers Market. The museum holds an incredible collection of Native American art, both from local Northwest coast tribes and those spanning the country. Over 3,500 objects from 200 North American groups sit on the second and third floors of the museum’s Confederated Tribes of Grand Ronde Center for Native American Art, teaching visitors about the original inhabitants of the land they currently stand on, as well as the cultural meaning behind each object. For visitors who want to connect with the history of the region, this experience is a must.

Hawthorne District

Exploring the Hawthorne District is one of the best things to do during a weekend visit to Portland, Oregon.
Credit: Portland Art Museum

If you’re in Portland for the weekend, don’t contain yourself just to the downtown Northeast area. Southeast Portland is home to many of the neighborhoods that make this city so unique — Hawthorne being one of them. Start by crossing the Hawthorne Bridge into SE, or park by SE 12th and make your way east. You’ll pass neighborhood staples like Cartopia, the late-night food truck pod hosting can’t-miss vendors like Potato Champion, the Gold Dust Meridian with its spacious back patio, and Waffle Window — it’s exactly what it sounds like.

The Hawthorne District is teeming with vintage stores and independent boutiques. Some of my favorites are House of Vintage, where you can spend hours poring over ‘80s dresses and old Playboy magazines, and Tender Loving Empire, where you can discover new music from local artists. Keep making your way down and you’ll reach Mount Tabor, Portland’s own mini-mountain with spanning views of the neighborhood at the top.

Where to Eat


Arden is one of the best places to eat while on a weekend trip to Portland, Oregon.
Credit: Arden

Locavore restaurants focusing on Pacific Northwest flavors are the norm in Portland, but there’s something special about Arden. The restaurant is cozy without feeling dated. The decor is inspired by grapevines and rustic greenery, framing the restaurant in the local flora. The food and wine fit the theme, with chef Erik Van Kley and owner Kelsey Glasser cooking with the seasons. Dishes include delicate salads, handmade pastas, local seafood, and a lot of duck. The wine list contains minimal-intervention offerings from around the world, with a spotlight on local Willamette Valley stunners. For those who are more Covid cautious or want to dine al fresco, the outdoor patio is heated and quite comfortable.


Berlu is one of the best places to eat while on a weekend trip to Portland, Oregon.
Credit: Berlu

Berlu’s chef Vince Nguyen has an inspired imagination and the cooking talent to back it up. You’ll need to purchase a ticket for a meal at this modern Vietnamese restaurant, where you’ll be one of just 12 other guests per seating. The meal itself is full of whimsy and intrigue; new plays on Vietnamese dishes, like grilled squid with coconut, onion, and lavender. Sometimes, lots of small things come out at once, like myriad presentations of crab or other seasonal fare. The menu is always dairy-free, and the restaurant is celiac-friendly and happy to accommodate. It doesn’t shy away from Covid precautions, either. Berlu recently put in MERV-13 filters in its HVAC, and has multiple air filters on during service. If you can’t make it for dinner, stop by on Sunday morning for Berlu’s bakery offerings — don’t miss the mango roll cake.


Kachka is one of the best places to eat while on a weekend trip to Portland, Oregon.
Credit: Kachka

Slavic food doesn’t have the great reputation that it deserves. The misconception that Slavic dishes are mostly mayonnaise and cured fish perpetuates — Kachka is on a mission to change that. The restaurant’s dishes pull from a host of Slavic favorites, like buttery pelmeni (dumplings filled with meat, cheese, cherries, or vegetables), skewers of lamb or halibut, spreads, fish boards, and about every pickle you can think of. The restaurant infuses its own vodkas, pulls from classic Russian and Ukrainian cocktails, and offers wine from Georgia, Hungary, and, of course, some local Oregon pours. Stop by its in-house deli and market to pick up some Slavic pantry staples to-go.

The restaurant is active in supporting Ukraine during the current occupation, having donated over $10,000 to the cause and being a constant voice in raising awareness.

Food Cart Pods

Food Cart Pods are a must to check out while on a weekend visit to Portland, Oregon.
Credit: Travel Portland

A visit to Portland isn’t complete without a stop at one of the city’s diverse food cart pods, a one-stop group of several different carts, all serving up unique flavors. There are at least 500 active food carts within the city limits — an incredible range of different styles, cuisines, and ethnicities, all with options within an accessible price range. Wherever you are in the city, you’re bound to stumble upon a cart pod with tons of options. Hawthorne Asylum in SE Portland’s Hawthorne District hosts 21 carts offering Guyanese, Iraqi, Burmese, Thai, Russian, and Korean cuisines. Third Avenue Pod in SW Portland has carts specializing in Vietnamese, Egyptian, Mexican, and Chinese fare. Get your choice of eats, and head over to find a spot on the waterfront like a local.