Top 16 Cool Things to do in Portland

From hipster hangouts to unique boutiques there are plenty of options in the country’s most hip cities if you’re one of the cool cats. In fact, it will be hard to know where to start, so we’ll help you along. Here are the best cool things to do during your next visit to Portland, Oregon…

1. Explore the Pearl District 

Pearl District Portland

The Pearl District is the quintessential place to enjoy the sight of boats on the San Antonio River while also browsing nearby art galleries (Froelick Gallery and Gallery 114) and boutiques (House of Lolo and Garnish). 

After you visit your favorite galleries and boutiques, stop by one of the nearby bars such as Teardrop Lounge for a cocktail and oysters with a plum mignonette. 

Try something new and go to Khao San for a delicious Thai meal in the Pearl District street setting. 

Address: Depends on the business you visit. The area spans 301 acres. 

2. Shop Vintage And Thrift Stores 

Best vintage stores in Portland, Oregon

Shopping vintage and thrift stores will give you retro, quaint, or even fancy possessions that are new to you but were once old and undesired by previous owners. 

William Temple House Thrift Store sells gently used clothing, secondhand furniture, and other new housewares that you can get at an affordable price rather than buying them brand new at a department store.

The House of Vintage showcases antiques, clothing from the 1920s to 2000s, vintage pop culture, and collectible items. Choose from one of the 60 dealers that are a part of the business to start browsing vintage wares today. 

3. Go for a brunch At Jam On Hawthorne 

Jam On Hawthorne cafe Portland

If you’re visiting the Buckman District, stop by the Jam on Hawthorne for a delicious brunch. 

There’s something for everyone at this breakfast and brunch restaurant with vast selections for vegans and vegetarians. If you’re a meat and potatoes kind of person, they have that as well!

Start your morning off with a zesty Bloody Mary or a spiked fruity mimosa to go with your breakfast. Choose from french toast sticks, scrambled eggs, chicken sausage, biscuits and gravy, loaded hash browns, and many more brunch dishes. 

Address: 2239 SE Hawthorne Blvd, Portland, OR 97214

4. Indulge in a sweet snack at Doe Donuts 

Doe Donuts vegan donuts

Whether you are vegan or not, you will enjoy having a snack at Doe Donuts in the Hollywood District. 

Choose from one of their year-round flavors such as the Doe (strawberry milk with sprinkles on it) or the Portland Fog which features an earl grey glaze and fair trade vanilla bean in it. 

If you’re feeling adventurous, try one of the seasonal donuts. This menu changes each month. For example, their month of April donuts are usually the marionberry snickerdoodle, veggie calzone, red velvet Krispie, and other flavors. 

Address: 4110 NE Sandy Blvd, Portland, OR 97212

5. Shop At the Union Rose boutique store

Union Rose Portland

Union Rose is a unique boutique in the Montavilla District that sells handmade clothing. Their in-house line is called Rita Hudson which is made on-location, which is why this boutique is one of the cool things to do in Portland. Shop dresses, blouses, gloves, pants, skirts, and T-shirts. 

While you will be paying a higher price tag than a department store clothing alternative, it’s very much worth it to enjoy the hand-sewn quality!

Besides their clothing, they also have bath and body products, jewelry, accessories, home goods, cards, stickers, and so much more. 

Try one of their DIY kits such as adult paint by number activities or natural dye shirt kits. 

Address: 8029 SE Stark St, Portland, OR 97215

6. Hang Out at the White Owl Social Club 

White Owl Social Club Portland

White Owl Social Club is your destination for a laid-back and interactive pub environment. 

Enjoy live music with friends or family while sipping on a Buckman Sour and eating a pulled pork sandwich. Maybe the Rancho Relaxo and a fish taco sound more up your alley. 

The Over-Under cocktail with raspberry grenadine and lemon would pair well with their spring salad. 

There are weekly events such as Taco Tuesdays and Rad Habits Thursdays. Select tacos and margaritas are $2 each on Taco Tuesday. A band called Rad Habits comes to visit White Owl Social Club every Thursday. 

The Weekend Spin is every Friday and Saturday night and features hit songs that will make you want to dance after you eat your meal. 

Address: 1305 SE 8th Ave, Portland, OR 97214

7. Go for dinner at the Doug Fir Lounge 

Doug Fir Lounge - Portland

Even if you do not stay at the Buckman District’s Jupiter Hotel, visit to eat dinner at Doug Fir Lounge and you will not be disappointed!

You will feel like you are on a camping trip while eating dinner because of the log cabin vibe in the restaurant. There are open live musical shows and performances from Wednesday through Monday. Check the schedule to see which local talent will be playing on the night you decide to visit. 

Try dinner favorites such as the rose garden salad, hummus plate, Eastside chicken strips, or the signature Fir Burger. 

Address: 830 E Burnside St, Portland, OR 97214

8. Try A New Sports Bar Experience at Sports Bra

Sports Bra Portland - cool things to do

Sports Bra is a new sports bar in Portland’s Sullivan’s Gulch District. 

While you dine, you can watch all women’s sports on their televisions. Sports bars usually feature predominantly men’s sports, but Sports Bra takes a different approach and showcases female sports only. This is why Sports Bra is one of the cool things to do in Portland as a woman. 

Try Mom’s Baby Back Ribs with a Cherry Picker cocktail or Sports Bra Nachos with a Pickle Ball cocktail. If you are vegan or vegetarian, you can try the Tempeh Reuben or the Sports Bar Pub Burger. 

This bar takes it a step further and features the women-only local distillery Freeland Spirits as their source of alcoholic beverages for their cocktails. 

Address: 2512 NE Broadway, Portland, OR 97232

9. Eat Cuban Vegan Food At Miami Nice

Cuban Vegan Food At Miami Nice

Miami Nice in the Buckman District offers Cuban vegan food. What makes their menu cool is how they designate each menu category with fun phrases. “Just the Munchies” features small Cuban vegan plates while “Super Hangry” features decked-out Cuban vegan entrees. 

Croquettas, empanadas, and tatertos make up the munchies menu. The Sloppy Bro, Miami Chop, and 305 Bowl are some of the dishes on their “Super Hangry” menu. 

One of their signature dishes is El Jefe. Steak seitan is homemade in the restaurant and sandwiched with shredded lettuce, tomatoes, and grilled onions. Enjoy the pepitas they put on the side. 

Address: 727 SE Grand Ave, Portland, OR 97214

10. Have a coffee at Upper Left Roasters 

Upper Left Roasters Portland

Upper Left Roasters in the Hosford-Abernethy District offers coffee brewed only with single-origin beans. Stop by the patio if you are visiting Portland during the spring or summer for a breezy and relaxing outdoor dining experience. 

Choose from drip coffee, cold brew, mocha, Americano, latte, and other signature coffee types made with their in-house brew as a base. 

To go with your coffee, enjoy a plain or almond croissant that’s buttery and flaky. If you want something more sumptuous, try a chocolate chip cookie or a wonder bun that looks almost like a cinnamon roll. 

Address: 1204 SE Clay St, Portland, OR 97214

11. Go for cocktails at Driftwood Room

Driftwood Room - Portland

Driftwood Room is located in the Hotel deLuxe in the Goose Hollow Foothills District. 

Try a bubbly champagne cocktail such as the Winter Story, Golden Ticket, or Portland 85. The signature champagne cocktail is the Driftwood Death in the Afternoon which features Lucid Absinthe Supérieure with a hint of lemon and is finished off with simple syrup for sweetness. 

The cool part about Driftwood Room is that some of their cocktails and martinis are named after actors such as Elizabeth Taylor and Clint Eastwood. 

Address: 729 SW 15th Ave, Portland, OR 97205

12. Visit Portland Art Museum

Portland Art Museum

Don’t forget to visit the Portland Art Museum while you’re in Downtown Portland.

Browse American, African, Native American, Northwest, Pre-Columbian, and Western art paintings and sculptures during your visit. If you appreciate professional photography, there’s a section for that as well. Get a taste of nationwide and worldwide history through the many art pieces that grace the museum’s walls. 

Exhibitions showcase special art pieces based on a theme or holiday for the month. Check out their upcoming exhibitions to prepare before your visit. 

Address: 1219 SW Park Ave, Portland, OR 97205

13. Explore the Hawthorne District 

Hawthorne Asylum Food Carts

Explore the Hawthorne District for delicious eats at local diners and pubs while stopping in between for adventures at shopping destinations such as gift shops and local boutiques. 

Try the Moroccan lamb meatballs at Sapphire Hotel. Let your food digest and grab a book from Powell’s Books or shop for old-school clothing at the House of Vintage. Once your meal has digested, get a sweet bite at Toadstool Cupcakes. 

Finish off your adventure in the Hawthorne District by visiting Mt. Tabor Park with your family which is located on an extinct volcano. 

Address: Depends on the business you visit. 

14. Dance at The Barrel Room 

The Barrel Room Portland Oregon

Old Town District’s Barrel Room showcases live piano performances and even high-stakes piano duels. No matter the music playing, you will want to dance the night away while drinking a cocktail or enjoying a small plate of delicious bar eats. 

When you’re done dancing at the Barrel Room, keep in mind that this bar is only 3 minutes walking distance to the Lan Su Chinese Garden. 

The business is undergoing new management and location transfer, so check back on their website for their grand reopening date. 

Address: 105 NW 3rd Ave, Portland, OR 97209

15. Explore Alberta Arts District

Alberta Arts District Portland

The Alberta Arts District is about a mile and a half starting on Martin Luther King Jr Blvd and down to Northeast 33rd Ave. 

The main event of eclectic art is located on NE Alberta Street. Go see a show playing at the Alberta Rose Theater. Check their website for show descriptions and showtimes. You can see live musical performances, comedy shows, and more. 

If you are planning a camping trip, Cord has you covered with mini and standard-sized camping gear and supplies.

16. Stay at the hipster friendly Ace Hotel 

Most Instagrammable places in Portland Oregon

Downtown Portland’s Ace Hotel is a 3-star venue situated in the old Clyde Hotel building. 

The Superior Deluxe Front Room features a king-sized bed, a desk for working online or surfing the web, and a large tub in the bathroom. The bathroom is not separated from the room by a door but by a white curtain, which is very unique. 

If you want to go on a budget, but there are 3 people including you in your party, you can get the Basic Shared Triple. This room features a bunk bed and a separate bed to sleep 3 people comfortably in the room. 

Address: 1022 SW Harvey Milk St, Portland, OR 97205


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