Things to Do in Portland: A First-Person Guide to Oregon’s Quirky City

Portland surprised me. I came for the coffee and nature but stayed for the quirky neighborhoods, hidden gardens, and cozy bookstores that made the city feel like home. If you love places with walkable charm, bold flavors, and a creative pulse, Portland is your kind of city.

Here’s everything I loved during my visit, from forest hikes to food-cart pods, plus some tips for exploring the city like a local.

Explore Portland’s Neighborhoods

Each neighborhood in Portland has its own personality, and exploring them is half the fun. Whether you’re a foodie, a shopper, an art lover, or someone who just loves wandering, here’s where to go:

Pearl District

Once a warehouse zone, this area has evolved into one of Portland’s most polished neighborhoods. It’s full of art galleries, upscale boutiques, cocktail bars, and some of the city’s best restaurants. I spent hours at Powell’s City of Books, the largest independent bookstore in the world, an easy place to get lost.

Nob Hill (NW 23rd Avenue)

Also known as the Alphabet District, this area is filled with historic Victorian homes, leafy streets, and stylish local shops. I grabbed a latte at a corner café and just people-watched for an hour, blissfully peaceful.

Alberta Arts District

This colorful neighborhood is bursting with creativity. Murals cover almost every wall, and the Alberta Street Fair is a must if you’re visiting in summer. Don’t miss the food carts or the live music spilling out of tiny venues.

Mississippi Avenue

Slightly more under-the-radar, this strip is ideal for vintage shopping, catching live music, or grabbing brunch. I loved Miss Delta for comfort food and browsed records at Mississippi Records next door.

Hawthorne & Division

These two adjacent eastside streets have a laid-back, bohemian vibe. Think tie-dye shops, record stores, independent movie theaters, and cozy book cafés. I recommend visiting Bagdad Theater, a historic cinema turned pub where you can sip a beer while watching a film.

Parks, Gardens & Outdoor Magic

You don’t have to leave the city to connect with nature. Portland’s green spaces are varied, accessible, and seriously relaxing. Here are the ones that made me feel like I had one foot in the forest even while staying downtown:

Washington Park

A sprawling park filled with mini-destinations. I started with a peaceful walk through the Portland Japanese Garden, known for its tranquil paths, koi ponds, and manicured landscapes. Then I wandered over to the International Rose Test Garden, which showcases thousands of rose varieties (and smells amazing in summer). The Hoyt Arboretum capped off my visit with a shaded forest trail walk.

Forest Park

One of the largest urban forests in the U.S., this place is a dream if you like trail running or quiet nature walks. The 30-mile Wildwood Trail connects to multiple scenic loops, and I ran into more chipmunks than people always a good sign.

Tom McCall Waterfront Park

Perfect for a morning walk or evening sunset. The path follows the Willamette River and passes under bridges, grassy areas, and seasonal cherry blossoms that transform the park in spring.

Tilikum Crossing Bridge

This car-free bridge connects the east and west sides of Portland and is open to pedestrians, bikes, and public transit only. I crossed it around golden hour and got some of the best skyline shots of the trip.

My Favorite Attractions

These experiences stood out and gave me a real feel for the city offering a mix of classic Portland charm, educational depth, family fun, and offbeat surprises:

Powell’s City of Books

The heart of Portland for book lovers. Spanning an entire city block, this iconic bookstore features over a million new and used titles. I browsed the color-coded rooms for hours, picked up a rare travel memoir, and found the staff recommendations surprisingly on point.

Pittock Mansion

Perched in the hills above the city, this historic French Renaissance-style mansion offers a glimpse into Portland’s pioneer past and breathtaking views of the skyline and Mt. Hood. The interior is beautifully preserved and perfect for architecture or history buffs.

OMSI (Oregon Museum of Science and Industry)

With hands-on exhibits, a planetarium, and a real decommissioned submarine you can tour, OMSI makes science genuinely fun. Ideal for a rainy day or if you’re traveling with kids (or just a curious adult like me).

Lan Su Chinese Garden

An authentic Suzhou-style garden in the middle of Old Town. With its stone pathways, koi ponds, and traditional teahouse, it felt like stepping into another world. I highly recommend doing the guided tour to understand its rich symbolism.

Oregon Zoo

Located within Washington Park, this zoo focuses on conservation and education. I particularly enjoyed the elephant habitat and the scenic zoo railway ride, which is great for young families.

Portland Puppet Museum

A tiny, whimsical museum that absolutely overdelivers on charm. Run by a puppeteer couple, it showcases vintage marionettes, global puppets, and occasional live performances.

Mill Ends Park

A blink-and-you’ll miss-it patch of greenery measuring just two feet wide, officially the world’s smallest park. It’s more of a quirky photo op than a destination, but undeniably Portland.

Wonderwood Springs

A hidden gem in St. Johns, blending immersive art and mini-golf. Each hole is part art installation, part fairytale adventure. Great for a creative date or a rainy afternoon.

Where I Ate (and Drank!)

Portland’s food scene is fun, experimental, and surprisingly affordable with something delicious waiting around every corner. I didn’t have a single bad meal during my trip, and these spots really stood out:

• Coffee – Tōv Coffee was one of the most memorable stops: a double-decker bus converted into a quirky, cozy café serving Turkish-Egyptian style drinks with bold flavors and beautiful presentation. I also loved the consistency and depth of flavor at Stumptown Coffee Roasters, and Coava impressed me with their minimal, wood-toned aesthetic and expertly brewed pour-overs. Portland takes its coffee seriously, and so did I.
• Food Carts – Portland’s food cart culture is unbeatable. Cartopia on SE Hawthorne offered wood-fired pizza and vegan poutine. Hawthorne Asylum felt like a lively food festival with mural-covered walls and dozens of carts ranging from ramen to Cuban sandwiches. Mississippi Marketplace had a more laid-back, local vibe and that’s where I found the best Thai fried chicken I’ve ever had.
• Donuts – While Voodoo Doughnut gets a lot of tourist hype, Blue Star was my go-to for quality ingredients and unexpected flavors. The passionfruit cocoa nib was tangy and rich in the best way. Pip’s Original Doughnuts deserves all the love too the mini donuts come hot and fresh with flavors like cinnamon sugar, honey sea salt, and nutella. Bonus: they serve phenomenal house-made chai in multiple spice levels.
• Ice Cream – Salt & Straw lived up to its legendary status. Their small-batch flavors range from seasonal local collaborations to mainstays like honey lavender or pear and blue cheese. Expect a line, but the staff is friendly and offers unlimited samples so you can make your perfect pick.
• Breweries – Portland is a craft beer haven. At Breakside Brewery, I tried a flight that included a dry-hopped pilsner, a hazy IPA, and a chocolate porter. Each one was distinctive and well-balanced. For something more offbeat, check out Cascade Brewing if you’re into sour ales they offer a tasting room with flights of tart, barrel-aged flavors that were unexpectedly refreshing.
• Rimsky-Korsakoffee House – I still think about this place. Hidden in a residential neighborhood, this café is part haunted house, part musical tribute, part dessert lounge. Tables slowly spin or rise unexpectedly, live classical music plays, and the menu is written on an old binder. I had a chocolate raspberry torte and coffee, and it felt like I’d stepped into a secret society. Don’t miss it if you love weird, wonderful places.

Day Trips from Portland

If you have a few extra days or even a free afternoon, Portland makes a perfect base for exploring some of Oregon’s most iconic natural wonders and charming small towns. Here are my favorite day trip ideas that are all within 90 minutes to two hours from the city:

• Columbia River Gorge – This dramatic canyon east of Portland is home to dozens of waterfalls and scenic hikes. Multnomah Falls is the most famous, but I found Latourell Falls and Wahkeena Falls to be less crowded and equally beautiful. Many trailheads are just off the Historic Columbia River Highway, making it easy to combine a few stops into one unforgettable loop.
• Mount Hood – Towering over the city on a clear day, Mount Hood is a must-visit for outdoor lovers. In the winter, it’s all about skiing and snowboarding at Timberline Lodge or Mt. Hood Meadows. In warmer months, you can hike through alpine meadows bursting with wildflowers, paddle in Trillium Lake, or just enjoy the panoramic views with a cold drink at Timberline’s historic lodge.
• Oregon Coast – A trip to the coast brings a breath of salty air and some of the most photogenic beachscapes you’ll ever see. I spent a relaxed day in Cannon Beach, walking the sandy stretch past Haystack Rock, browsing cute bookstores and galleries, and grabbing chowder at a local seafood shack. Other coastal towns like Manzanita or Seaside are also worth exploring if you have more time.
• Willamette Valley – Known for its Pinot Noir and rolling vineyard landscapes, this wine region is only about an hour from the city. I visited a few small, family-run wineries near McMinnville and Dundee, where tastings came with stories and vineyard views. Even if you’re not a big wine drinker, the scenic drives and local farm-to-table spots make this area special.
• Vista House – On your way through the Columbia River Gorge, don’t miss this historic viewpoint perched on a cliff above the river. Built in 1918, the Vista House offers sweeping views of the gorge below and is especially stunning at sunset. There’s also a small visitor center and photo-worthy stonework inside.

Each of these destinations shows off a different side of Oregon mountains, waterfalls, beaches, and vineyards, and they’re all within reach of a Portland home base. Bring layers, a good camera, and a sense of adventure!

Getting Around Portland

• MAX Light Rail & Streetcar – An Easy and affordable way to get around the city.
• Biketown – Portland is super bike-friendly, and rentals are easy.
• Walking – Most neighborhoods are compact and fun to explore on foot.

Markets, Events & Tours

Portland Saturday Market

One of the longest-running outdoor markets in the U.S., this riverside event pops up every weekend from March through December. It’s a great place to shop for handmade pottery, paintings, jewelry, and quirky souvenirs while snacking on food truck fare and catching live music performances. I picked up a handmade notebook and watched a local blues band play under the bridge.

Portland Night Market / Snack Fest PDX

Held several times a year in the Central Eastside Industrial District, this high-energy night market blends street food, artisan vendors, DJs, and art installations. I wandered through aisles of indie brands, tasted Filipino lumpia and bubble tea cocktails, and danced to a surprise live set in a back warehouse.

Willamette River Cruises

If you’re looking to see the city from a different angle, hop aboard a cruise boat that floats along the Willamette River. They offer everything from narrated lunch tours to romantic sunset dinners with live piano music. It’s a relaxing way to take in skyline views, especially with a glass of local wine in hand.

Shanghai Tunnels Tour

Portland’s Old Town hides a maze of underground tunnels once used for moving goods and, allegedly, people during the city’s darker, more lawless days. This guided tour blends history with a touch of the paranormal, making it a unique way to learn about the city’s past. Bring comfortable shoes and a curious spirit.

Ground Kontrol & High Scores

These two retro arcades are a blast from the past, packed with classic pinball machines, 80s and 90s video games, and neon-lit vibes. Ground Kontrol also serves drinks and hosts themed nights, while High Scores is more family-friendly. I loved challenging myself to beat my old Pac-Man score with a cider in hand, pure nostalgia.

When to Visit Portland

• Spring – Ideal for cherry blossoms and fresh blooms in the gardens.
• Summer – Festivals, food carts, and sunny weather.
• Fall – Crisp air, colorful foliage, and fewer crowds.
• Winter – Cozy cafes and easy access to snowy day trips.

Where to Stay

• Downtown/Pearl District – This area is perfect if you want to be in the middle of everything. You’ll be close to top attractions like Powell’s Books, the Portland Art Museum, and countless restaurants and coffee shops. It’s well-connected by public transit and super walkable. The vibe here is urban, upscale, and energetic great for first-timers or short weekend stays.
• Alberta & Mississippi – These eastside neighborhoods are where Portland’s quirky, creative energy really shines. You’ll find colorful murals, unique boutiques, record stores, and some of the best food carts and brunch spots in the city. Staying here feels more local, with charming guesthouses, boutique hotels, and Airbnbs tucked into leafy residential streets. Perfect for travelers who want character and culture over high-rises.
• South Waterfront – Sleek, quiet, and scenic, this area offers modern condo buildings and hotels along the Willamette River. It’s ideal if you’re looking for a more peaceful base with lovely walking paths and easy access to the aerial tram up to Oregon Health & Science University (with amazing views!). It’s a bit less central, but a good fit for longer stays or travelers who prefer quiet evenings and water views.

FAQs About Visiting Portland

Final Thoughts

Portland charmed me with its balance of nature and city, tradition and quirk. Whether you’re into food, hiking, books, or bikes there’s something here for you. I hope this guide helps you discover your own favorite pockets of the city.