Introduction
Hey there! I’m so excited you’re thinking about visiting Portland, Oregon – one of my favourite cities in the US. I recently spent a long weekend there and came away totally charmed, and I found so many fun things that I want to share with you. Whether you’re into nature adventures, quirky urban finds, foodie delights or just strolling through cool neighborhoods, Portland blends both laid-back and off-beat in a unique way.
In this guide, I’m going to walk you through twelve of the best and most fun things to do while you’re in town. I’ll mix in my own experiences, plus practical tips (for avoiding crowds, timing things right, making the most of the vibe). And I’ll include plenty of pictures so you can really imagine yourself there. Let’s dive in!
12 Best & Fun Things To Do In Portland, OR (2025)
1. Visit the Iconic Bookstore: Powell’s City of Books
If you love books, this is the place. Powell’s occupies an entire city block in Portland and is known as the world’s largest independent new & used bookstore.
Why you’ll love it: You can easily wander for an hour (or more!) among tens of thousands of titles; grab a coffee, people-watch; pick up a local gem or a rare book.
My tip: Don’t rush. Pick one section that intrigues you, sit for a few minutes and soak in the vibe. If it’s rainy, this spot is perfect to escape the weather.
Best time: Morning on a weekday if you can — fewer crowds.
2. Stroll Through Washington Park (Japanese Garden, Rose Garden & More)
This large 400-plus acre park is a favourite of mine for both nature and relaxed city-escape vibes. Within it you’ll find the beautiful International Rose Test Garden, with more than 10,000 rose bushes and over 610 varieties. And the serene Portland Japanese Garden, which offers a peaceful contrast to the bustling city.
Why you’ll love it: It’s the perfect “nature & calm” break during a city trip. You’ll get views, fresh air, quiet moments.
My tip: If parking looks full, take transit (MAX light rail lines serve it). Also bring a water bottle and wear good shoes if you want to explore some of the trails.
Best time: Late morning to early afternoon — the light for photos is great, and the gardens are in full bloom during late spring through summer.
See Also: 45 Fun Things To Do & Places To Visit In West Virginia
3. Grab a Bite (or Many) at the Food Truck Pods
One of the things that makes Portland super fun is how seriously it takes its street-food scene. There are many “food truck pods” around town where you’ll find everything from fusion tacos to vegan delicacies.
Why you’ll love it: Flexibility (choose from many cuisines), casual atmosphere (great for solo travellers or groups), and budget-friendly.
My tip: Head to one around lunch (11:30–12:30) to beat the major lines; bring cash or check if your truck takes cards; and share — you’ll want to try more than one thing!
Best time: Lunch to early afternoon; evenings can also be fun but sometimes a bit more crowded.
4. Ride the Portland Aerial Tram for Epic Views
For a bird’s-eye view of Portland, hop on the aerial tram. It gives you a unique vantage point and is a fun little adventure.
Why you’ll love it: The ride is short but memorable, and it gives a refreshing perspective of the city and surrounding nature.
My tip: Bring a camera! Sit on the side facing the city skyline. Check weather — on a clear day the views are spectacular.
Best time: Late afternoon, when the sunlight softens and you might catch sunset hues.
5. Wander Through the Artsy Neighbourhood of Alberta Arts District
This neighbourhood is bursting with street art, independent cafés, quirky boutiques and a really good local vibe.
Why you’ll love it: It feels like you’re discovering the “real” Portland, beyond the typical tourist zones. Lots of photo opportunities.
My tip: Take your time strolling Alberta Street; stop in a café, peek into a gallery, chat with locals.
Best time: Mid-morning on a weekend when local galleries might have open hours and the street is lively.
6. Explore Quirky Spots – Because Portland Does Weird Well
Part of what makes Portland so memorable is its quirky, off-beat side. From oddball museums to hidden art installations, you’ll find those little surprises that make travel fun. For instance: the city’s public art and mural scene is rich and vast.
Why you’ll love it: These spots give you unique experiences you won’t find in every city. Great for wanderers, curious travellers, photo lovers.
My tip: Keep your eyes open: walk down side streets, peek into tucked-away galleries, ask locals for their favourite odd-ball spot.
Best time: Anytime; evening light can give murals interesting shadows.
7. Visit the Riverside Walk at Tom McCall Waterfront Park
Walking along the river is relaxing, scenic and very accessible. Tom McCall Waterfront Park lies right along the Willamette River and is a great way to soak in the city from a different vantage.
Why you’ll love it: It’s calm, beautiful, easy. You can pair it with a food stop, or just stroll and take some deep breaths.
My tip: If you’re there on a Saturday morning, check out the market (if active). Late afternoon is also pretty.
Best time: Early evening, when the light hits the water softly and the city lights begin to glow.
8. Head Out of Town for a Waterfall or Gorge Day Trip
One of the best things about Portland is how quickly you can access nature. Within a short drive there are beautiful waterfalls, forested trails and scenic escapes.
Why you’ll love it: A change of scenery, fresh air, possibly a little adventure. Great for clearing your mind and stretching your legs.
My tip: Rent a car for the trip, or join a guided tour if you prefer. Wear good hiking shoes, bring a light jacket (waterfalls = mist!).
Best time: Warm season (spring to early fall) when trails are most accessible.
9. Experience the Saturday Market in Old Town
The local Saturday market is a lovely way to spend a morning or early afternoon, browsing crafts, food, local art, and meeting locals.
Why you’ll love it: Authentic local culture, unique souvenirs, a friendly relaxed atmosphere.
My tip: Go early for better parking and fewer crowds; bring some cash; try a local snack while you’re there.
Best time: Saturday morning to midday.
10. Go for Craft Beer & Breweries (or a BrewCycle Experience)
Portland is famous for its craft beer scene, microbreweries, and fun ways to explore them (like the witty “BrewCycle” tours).
Why you’ll love it: Great beverages, quirky atmospheres, and you’ll feel like you’re joining a local ritual.
My tip: If you’re doing bar-hopping, pick one neighbourhood and walk or bike between spots rather than trying to cover multiple across town. Drink responsibly.
Best time: Late afternoon / early evening, when breweries are setting into their rhythm.
11. Visit the Neighborhood of Food & Drink on Mississippi Avenue
This is a lively, up-and-coming area with lots of good restaurants, cafés, and nightlife options. One of my favourite meals in Portland was on Mississippi Avenue.
Why you’ll love it: Great mix of food, local design, relaxed energy, less touristy than downtown.
My tip: Choose a brunch stop, then wander the street, explore shops, maybe finish with a craft cocktail.
Best time: Brunch time on a weekend (late morning) or early evening for dinner.
12. Relax, Explore & Just Let the City Surprise You
Sometimes the best part of a city is simply letting it unfold. Portland has a mellow charm, unexpected cafés, rainy-day corners, hidden alleys and plenty of surprises.
Why you’ll love it: It’s low-key, authentic, and you’ll discover something memorable on your own.
My tip: Leave free time in your itinerary. If the forecast shows rain, embrace it — the city’s green and moody in those conditions. Try a café, wander aimlessly, don’t feel like you have to “see everything”.
Best time: Any time — just when you feel like slowing down.
Final Thoughts
And there you have it — twelve of the best and fun things to do in Portland, Oregon — from big iconic stops to hidden gems and everything in between.
Here’s what I’m taking away from my visit:
- Portland has range: you can go full-nature escape one morning and urban foodie adventure the afternoon.
- The city invites you to slow down and enjoy rather than rush through.
- Bring layers (the weather can shift), comfortable shoes (walking & exploring), and a curious spirit.
- Don’t over-schedule — some of the best experiences are unplanned.
- Embrace the “weird” and local side of Portland — that’s where the magic often lies.
If I had to pick a “must do” if you only had one day: spend the morning in Washington Park (garden + nature), hit Powell’s for a wander, then end with dinner in a fun neighbourhood like Alberta or Mississippi Avenue. That combo gives you nature + culture + food in a nicely balanced way.
Safe travels, and I hope your time in Portland is every bit as fun as mine was.