55 Wildly Original Portland Adventures You’ll Only Find Here

Portland is a small but vibrant city known for its quirky character and lush green spaces. The city’s laid-back atmosphere is complemented by its scenic beauty, from the Willamette River to the incredible views of Mount Hood.

A gateway to Oregon’s beaches, mountains, waterfalls, and rivers, it is the perfect base for those looking to explore nature but enjoy the creature comforts of a city stay. With its unique blend of progressive values and offbeat charm, Portland is a proud hipster paradise.

Made famous by synonymous satirical comedy Portlandia, where stereotypical city locals are passionate about the arts, vegan food, craft beer, eco-conscious living, and everything artisanal. It’s a must-visit destination for foodies and lovers of thrifting, nature, and the arts. 

This list covers many of Portland’s well-known landmarks PLUS places that no other guides tell you about. Here is the insider’s guide to the best things to do in Portland, the beloved hipster capital of the world.

Outdoor Activities

Are you craving some time in nature or just looking for a peaceful spot for a picnic lunch? Portland has many green spaces within the city and is a short drive or bus ride from many national and state parks. Here are some of the area’s best-guided tours, parks, and outdoor adventures.

1. 4-T Trail: Get your urban explorer on and tour Portland on the 4-T Trail. It combines four types of transport: walking, train, aerial tram, and trolley. Start with a hilly hike to the city’s highest point, then glide 3,300 feet downhill in the aerial tram to Portland’s riverfront to continue your one-day city adventure.
2. International Rose Garden: Portland is called “Rose City.” Head to the flower garden during the summer season to see why. You can admire hundreds of beautiful varieties.
3. Tryon Creek Guided Hikes: Join educational hikes on various topics led by a park ranger.
4. Pittock Mansion: Tour a historic 1914 mansion and learn about Portland’s history from the pioneer days to the present.
5. Oregon Zoo: Portland offers a great zoo if you love visiting zoos. However, this is a pretty typical zoo, so if you’re looking for more local experiences, it might not be the highest priority on your itinerary.
6. Kayaking: Rent a kayak or canoe and spend an afternoon cruising the Willamette River. Camping sites are also available, making it a multi-day trip.
7. Eastbank Esplanade: Walk, run, or bike along the Willamette River to stay active and soak up Oregon’s natural beauty.
8. Forest Park: Hike or bike through the largest urban forest in the United States.
9. Oregon Coast Day Trip: Take a scenic drive to the Oregon Coast for stunning views and coastal towns. Cannon Beach and Cape Perpetua are popular choices.
10. Columbia River Gorge: Hike to waterfalls and scenic viewpoints and explore charming towns along the Columbia River. Cascade Locks is a noteworthy town, home to the Bridge of The Gods. The only bridge to span the Columbia River it connects Oregon and Washington states. It is a highlight of the Pacific Crest Trail. It is a toll bridge, even for pedestrians, but it is worth the small price for the picturesque views. While you’re there, stop by Thunder Island Brewing Co. for a refreshing beer and their signature vegan buffalo cauliflower.
11. Mount Hood: Visit Oregon’s tallest peak for skiing, snowboarding, hiking, and stunning views.
12. Sauvie Island: Enjoy outdoor activities like hiking, birdwatching, and berry picking on this rural island—a perfect family-friendly day trip. 
13. Hood River: This charming town is known as the windsurfing capital of the world. It is also famous for its breweries, wineries, and fruit orchards.
14. Mt. St. Helens: Take a day trip to the area near Mt. St. Helens, the most active volcano in the United States. It famously erupted in 1980, leaving behind a unique landscape. Accessing the peak is prohibited for safety, but you can still admire the landscape at the base and natural regeneration. It’s about a 1.5-hour drive north of Portland, and guided tours are available.
15. Mill Ends Park: Visit the world’s smallest park for the novelty! It is a small patch of soil with a tree in the median street at the intersection of SW Taylor and Naito streets. Fun for a photo op.
16. Lan Su Chinese Garden: This classical Chinese garden is a touch of serenity in the heart of Portland. If you need a mindful pause after a busy day of sightseeing, this spot is a great choice. There are programs and classes throughout the year to learn more about Chinese culture.
17. Portland Japanese Garden: A large, traditional Japanese garden spanning 12 acres on the city’s edge. It is a peaceful and immersive garden popular with tourists and locals alike.
18. Ride the Red Electric: Ride in a replica vintage trolley from the 1800s from Lake Oswego. The trolley passes through a dark tunnel and some of the more upmarket suburbs of Portland. 
19. Pedalounge: Exercise and alcohol combined, but it works! Possibly the most unique bar you will ever visit, the Pedalounge is a 16-seat group bike and built-in bar. Book a spot with friends (or meet some new ones) and pedal around Portland while enjoying the local beers. Tours last about two and a half hours.

Food and Drink

Portland is known for its breweries, food trucks, and a wide variety of cuisines. It’s also very dietary-friendly, with dedicated gluten-free and vegan restaurants. Here are some of the must-visit venues.

20. Punch Bowl Social: Enjoy cocktails, bowling, and karaoke at this quirky bar.
21. Portland Farmers Market: Explore a vast farmers market with produce and baked goods. You can also buy a wide range of prepared foods from rotating local vendors — think pierogies, pizza, burritos, rice bowls, Jerusalem salad, falafels, and many others. The market is open every Saturday. 
22. Get Your Pizza Fix: For deep-dish and vegan options, head to Apizza Scholls, Gladstone Street Pizza, Ken’s Artisan Pizza, or Boxcar Pizza. These restaurants serve some of the best pizzas in Portland.
23. Cascade Brewing: Portland is known for its many breweries and artisanal beer. At this local brewery, you can sample barrel-aged sour beer.
24. Rimsky-Korsakoffee House: Get coffee and dessert in a haunted house! The epitome of Portland’s quirky eateries, this converted 1902 Craftsman home is one of Portland’s oldest coffee houses. It is named after a Russian composer and has a classical, spooky theme throughout.
25. Kachka restaurant: Try delicious Eastern European cuisine like dumplings, cured fish, and mushroom stroganoff. Kachka also serves over 50 different vodkas!
26. Franz Bread Factory: Get a peek inside a commercial bread factory by looking through the Franz bakery production line window.
27. Schilling Cider House: Celiacs rejoice! At Schilling Cider House, you can taste 50 local hard ciders on tap PLUS enjoy an entirely gluten-free menu.
28. Bagdad Theater & Pub: Experience a full-service theater and pub with shuffleboard and pool.
29. Portland Mercado: Explore a food cart pod featuring cuisine from Latin America.
30. Hopscotch: This large 23,000-square-foot gallery is interactive and family-friendly. Enjoy the all-ages immersive and playful art installations and grab a bite to eat at the cafe. 
31. Slappy Cakes: Make pancakes at your table with built-in griddles and an assortment of toppings. This is a restaurant where it’s okay to play with your food! 
32. Hawthorne Asylum: One of the larger food cart pods in the city, with about 20 carts and lots of covered seating. A foodie paradise!
33. Salt & Straw: This local chain is known for its delicious, small-batch ice cream with unique flavors. It has multiple locations across Portland, and now the world.
34. Tilt: Feast on gourmet burgers, biscuits, and old-fashioned cream pies in a retro blue-collar-inspired setting. Tilt is a local Portland chain of restaurants that is classic diner food at its finest.
35. Screen Door: Get Southern-inspired comfort food in a fine dining style.
36. Electric Lettuce: If you’re over 21, you can buy recreational cannabis at one of the Electric Lettuce dispensaries — there are a few around Portland. It’s 4:20 p.m. somewhere!
37. Voodoo Doughnut: Indulge in unique and colorful novelty-shaped doughnuts. There are lots of vegan options!

Arts and Culture

Portland is known for its creative culture. A great way to spend a day in Portland is by checking out the local history, art, museums, and exhibitions.

38. World Forestry Center: If you love forests, this unique museum has exhibits on the flora, fauna, and the essential role that forests play in the global and local environment. 
39. Freakybuttrue Peculiarium: A private collection of oddities relating to sci-fi, horror, cryptids, and the mysterious.
40. Portland Art Museum: Explore art from around the world at one of the oldest art museums on the West Coast. The Portland Art Museum boasts an extensive permanent collection of over 42,000 pieces, including Native American and Asian art, as well as modern and contemporary works.
41. Oregon Historical Society: Described as a love letter to Oregonian history, the historical society collects artifacts, photographs, books, and much more.
42. Oregon Museum of Science and Industry (OMSI): A family-friendly museum where you can explore hands-on science exhibits and laboratories.
43. Oregon Rail Heritage Center: Visit a free train museum and enjoy $14 train rides from March to September.
44. Alberta Arts District: The Alberta neighborhood in Northeast Portland is known for its galleries, boutiques, and restaurants.
45. Mississippi Avenue: Another lively Portland locale full of quirky shops, cafes, and food carts. Meander through the area to shop, eat, and explore.
46. Last Thursday on Alberta: During the summer, Alberta Street closes off all traffic and comes alive between 6-9 p.m. with musicians, local makers, performers, and food vendors. Check it out on the last Thursday of June, July, and August. 

Entertainment

If there’s one thing Portland is not, it’s boring. The city has many entertainment options at affordable prices suitable for families and adults. Whether you’re craving a movie, games, or a live performance, Portland delivers.

47. Glowing Greens: Play a round of mini-golf at this indoor blacklight 3-D adventure course! If you need something more thrilling, there’s also an escape room and axe-throwing on site.
48. Ground Kontrol: Get playful at this affordable arcade and bar. Just $10-20 can last you hours.
49. Yacht Tubs: Feeling bougie? Grab your swimsuit, a bottle of champagne, your closest friends, and rent a luxurious small boat with a hot tub. Self-pilot the boat down the Willamette River, boarding at Riverplace Promenade.
50. Living Room Theatres: If you’re craving some downtime, grab tickets to a movie and enjoy a proper meal at the same time. Living Room Theatres has a full drink and food menu, plus they’ll bring the meal to your assigned seat mid-movie — a civilized cinema experience.
51. Providence Park: Portland is a city with soccer fever! Attend a local match to watch one of the two Portland teams: the Timbers and the Thorns.
52. Pips & Bounce: Play ping pong with unlimited balls at this wholesome bar.
53. Darcelle XV: Portland loves a good drag show. Darcelle XV has been a local institution since 1967 — this is a fun, campy female-impersonator cabaret show. It is a small venue, so be sure to book in advance.
54. Quarterworld: Have fun at this inclusive and laid-back arcade in Hawthorne. Home to 30+ pinball machines, plus retro, modern, and physical games, it’s a great family or fun date night experience. They also have a bar and snacks. Plus, you can indulge your inner child for a bargain price — each game only costs 25 cents!
55. Enchanted Forest: Enjoy this family-operated magical theme amusement park. It operates during spring break, summer high season, and some weekends in the fall. Check the website for more information.

Portland is a fantastic travel destination for nature lovers, foodies, and those interested in arts and culture. Whether hiking, beer-cycling through the city streets, floating down the Willamette River in a hot tub, or applauding a drag show, Portland’s quirky culture guarantees a welcoming and unique vacation experience that you’ll be talking about for years to come.

This article originally appeared on Travel Binger.

Don’t close that tab just yet…Where to Next in Oregon?

I’ve vanlifed up, through, and about all of West Oregon three times now. If you’re looking for more information on Oregon, check out these other destination itineraries.

• Perfect One Day In Crater Lake Itinerary For First-Timers
• One Day in Portland Itinerary: Best of the City in 24 Hours

MY FAVORITE TRAVEL RESOURCES

✈️ Find amazing guided tours and experiences with Viator to maximize your time! 🏘️ Plan ahead and secure your accommodation with Booking.com in advance. 🧾 Rent a car with Discovercars in advance and get the best prices for your day trip adventures.