How to Spend One EPIC Day in Portland, Oregon

Crafting this guide was no easy feat, but I’ve never been one to shy away from a challenge. As a lifelong local I have a laughable long list of local gems I love to share with out-of-town visitors. I figured it might be fun to compile the list into a one day itinerary for anyone planning a quick trip to my stomping grounds.

Condensing all that makes Portland special into a single, manageable day is quite the ask! While it’s true that there’s a handful of iconic attractions to visit, the city offers so much more than viral sensations. With some thoughtful planning, you can get a good feel for the city (and perhaps get an itch to return!).

Drawing on my life-long experience, here’s exactly how I’d choose to spend one day in Portland. From beautiful parks, incredible restaurants and no shortage of quirky vibes, let’s dive in!

Note for you, dear reader: If anything in this post doesn’t make sense (or if you have any questions), don’t hesitate to let me know in the comments below. I want your one day in Portland to be enjoyable and I’m here to make that happen. I love hearing from you!

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Is One Day Enough Time?

The honest answer is no, but it’s better than nothing — we’ll take what we can get! Simply put, there’s just too much to see and do (not include the epic nature a short drive outside the city!).

​If you have just one day in Portland, it’s possible to experience some of the city’s highlights. A well-planned day could include a short morning hike, exploring downtown, and spending the evening at a swanky restaurant worth the hype.

With one day, you’ll get a nice introduction to the city, but it takes more than a single day to fully appreciate everything on offer, so go easy on yourself. Who knows? Maybe you’ll be enticed to return for longer visit sometime soon, that way you can enjoy all the great things to do in Portland.

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Trust Issues? Me Too. So Let Me Introduce Myself

I’m a lifelong Portland local. I grew up in the City of Roses and spent most of my weekends exploring the city and surrounding areas. Portland saw me through all of my major life moments, from high school and college to my first real job (at the City of Portland!) to my venture into entrepreneurship (mercy).

I’ve celebrated milestones in various Portland restaurants and bars. I’ve seen the city fall into a slumber during COVID and slowly rise again – and through it all, I’ve loved every minute of my time here. I’m also an avid reader and have done my fair share of learning about Portland’s history. I plan to share some of the most interesting facts with you below.

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How to Spend One Day in Portland, Oregon

​When it comes to spending a day in Portland, there are countless ways to make magic happen. You could park yourself at a charming cafe, go brewery-hopping like a local or get lost at Powell’s Books.

With just a single day, diving deep into one particular aspect might be challenging. Instead, consider this guide as a curated sampler of Portland’s more unique offerings, designed to provide a well-rounded itinerary for most interests.

Throughout the day, you’ll find yourself soaking in scenic hills overlooking downtown, exploring the heart of the city, and then crossing the Willamette River to discover the distinctive neighborhoods that even locals consider irresistible.

Where to stay in Portland? This is probably the most common question I get. This is my favorite hotel in Portland, I recommend it to my own family and friends. If you’d like more options, here’s my roundup of the 12 best hotels in Portland (for all budgets).

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Start your day right

Ah yes, the thing Portland is most famous for – great coffee. And we live up to that reputation! It’s hard to go wrong in this department, but I’d recommend visiting one of these cafes to kick start your day in the City of Roses.

• Stumptown Coffee at the Ace Hotel: We can’t talk about the best coffee in Portland without mentioning the original, Stumptown Coffee. Still considered the most iconic coffee shop in Portland, this gem has spread to several locations across the country. Swing by to see why locals maintain a steadfast devotion to Stumptown regardless of all the new cafes that have cropped up over the years.
• Coava Coffee Roasters: Coava roasts its own beans, which are so well known that many Portland cafes choose to use them exclusively. Specializing in pour-overs and espresso, rather than latte art, this is the place to go if you want a great cup of coffee with a focus on the beans. The baristas are some of the friendliest I’ve come across and take great pride in sharing their knowledge of the day’s beans.
• Never Coffee: A tiny but light-filled charming Portland cafe, Never Coffee has become Instagram-famous thanks to the colorful decor and great coffee. Served in cheery and vibrant ceramic mugs, the flavored lattes at Never Coffee are the crowd favorites. Perfectly executed, these creative concoctions feature seasonal flavors like yuzu, fennel and shishito peppers.

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Visit Portland’s Most Popular Park, Washington Park

Washington Park is the crown jewel of Portland’s robust park system and it’s not hard to see why. Located on the border Northwest Portland, this breathtaking park spans 400 acres and houses six important cultural institutions:

• The International Rose Test Garden (must-see)
• Portland Japanese Garden (must-see, especially in the fall)
• Oregon Zoo
• Hoyt Arboretum
• World Forestry Center

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The Portland Rose Garden

Portland is often referred to as the City of Roses because the local climate creates the perfect conditions for growing roses. Nowhere is this more evident than at the exceptional Portland International Rose Test Garden within Washington Park.

Portland’s beloved rose garden is both the largest public rose garden in the country. Home to an impressive display of 650+ varieties of roses (more than 10,000+ bushes), it’s easily one of the best free things to do during 1 day in Portland.

The history of the rose garden is equally fascinating. Originally started in 1915 by Jesse Currey, (Editor at the Oregon Journal and rose hobbyist), the rose garden was created in an effort to preserve roses susceptible to eradication during World War I. In my book, this is a must-see Portland attraction.

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The Portland Japanese Garden

Opened in 1967, the well-curated Portland Japanese Garden provides a calming escape from the hustle and bustle of city living. If you find yourself overwhelmed by concrete, head over to reset the senses. The garden is regarded as one of the most authentic Japanese gardens in America, reason alone to visit during your 1 day in Portland.

I can’t recommend this experience enough, especially if you’re visiting during the fall months when the garden comes alive with exceptional fall color. Make sure to swing by the cozy Umami Cafe for a little tea break, you won’t be disappointed.

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Brunch in Northwest Portland

When it comes to great food, Portland doesn’t mess around. So after your morning trek through Washington Park, I suggest you properly refuel. You’ll be very close to Northwest Portland (my stomping grounds!), so I suggest grabbing some brunch in the neighborhood.

Here are some recommended spots for breakfast, brunch, or donuts in the vicinity:​

• The Screen Door: Offering perfected southern dishes, Screen Door is most famous for serving the best chicken and waffles in Portland. Folks wait 1+ hours to get their grubby little hands on the indulgence.
• Pine State Biscuits: Known for their hearty breakfast sandwiches, this Portland staple is slightly off the beaten path but worth the visit if you’re craving something savory after your hike.
• Ken’s Artisan Bakery: My favorite place on earth! Established by a local baker who authored this award-winning cookbook, this neighborhood bakery often sees lines on weekend mornings, a testament to its popularity. They also operate a wood-fired pizza spot (Ken’s Pizza) across the river, which I love too).​

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Get Lost at Powell’s Books

Located within the Pearl District, Powell’s Books spans an entire city block and has an interesting claim to fame: it’s the largest independent bookstore in the world. Home to more than one million new and used books, it’s a haven for bibliophiles. If that sounds overwhelming, grab a map before embarking on the adventure.

You can easily spend hours exploring its nine color-coded rooms, each housing a vast array of genres and subjects. Whether you’re searching for a rare first edition or the latest bestseller, Powell’s likely has it in stock. ​

The store also hosts frequent author events and offers a Rare Book Room, which houses approximately 9,000 valuable books, including autographed copies and first editions. Fun fact: The most expensive book at Powell’s is an 1814 copy of the Lewis & Clark Journal which includes Captain Lewis’ map. The price? $350,000.

A visit to Portland would be incomplete without spending time at Powell’s, book lover or not!

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Explore the Pearl District

Powell’s is housed in Portland’s trendy Pearl District. Best described as industrial chic, towering high rises (with rent prices to match) have cropped up around historic red-brick buildings, the old and new blending together seamlessly.

This Portland neighborhood is popular among locals because of the charming independent boutiques, cafes, cozy bars and art galleries. Originally home to warehouses and loading docks, the Pearl has recently reinvented itself as the premier destination in the city.

The warehouses have since been converted into airy light-filled condos and the cobblestone streets of yesterday lead the neighborhood into the future. Today the beloved Pearl District serves as a testament to the power of breathing new life into a (once) neglected area, to everyone’s benefit.

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Stroll Tom McCall Waterfront Park

Tom McCall Waterfront Park is named after Oregon’s revered governor. Route yourself to the stretch between the Burnside and Hawthorne Bridges for prime people-watching. The park swells with locals, so expect to dodge bikers, walkers, skateboarders and young couples walking hand-in-hand.

If you’re visiting on a Saturday, the Portland Saturday Market operates under the Burnside Bridge. The market showcases local artisans offering a wide range of handmade arts and crafts, from photography prints to leather goods.

Better still, if you’re visiting Portland in the spring, strolling Tom McCall is a no-brainer because this is the best spot in Portland for cherry blossoms. The 100 Akebono cherry trees that line the waterfront were gifted by the Japanese Grain Importers Association in 1990.

Local’s Recommendation: Sit on a bench for a few minutes and watch the world go by while enjoying lunch from the nearby Pine Street Market. I love the pizza stall and used to come here once a week when I worked downtown.

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See the Second-Largest Copper Statue in America

At 35 feet high, the Portlandia Statue is the second-largest copper statue in America, second only to the Statue of Liberty in New York City. It’s located in the heart of downtown Portland.

You might ask yourself why such an iconic statue is not better known. Well, the sculptor guards the rights to the statue strictly and doesn’t allow photos of it to be used for commercial purposes (he’s notorious for threatening lawsuits when his request is not met).

However, the statue may look familiar to Portlandia fans because the show received permission to use the statue after hefty negotiations and an agreement not to use it in a “disparaging way.”

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Take a Photo With the Keep Portland Weird Mural

No proper one day Portland itinerary is complete without a visit to the Keep Portland Weird mural. Cheesy? Sure but don’t skip it unless you’re lactose intolerant (so sorry about that, couldn’t resist).

The reason is simple, if you don’t take an obligatory photo with the Keep Portland Weird mural then nobody will believe you ever spent a day in Portland. So route yourself to this mural and let the magic happen.

The mural has become synonymous with the city’s lifestyle and feels like a call to action for some locals. You’ll see the slogan on bumper stickers, t-shirts, posters, you name it.

Apparently the motto was originally borrowed from Austin, Texas (how one “borrows” a motto is beyond be, but I digress). It was brought to Portland in 2003 by Music Millennium owner terry Currier with the intention of supporting local businesses.

Location: 22 SW 3rd Ave, Portland, OR 97204

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Explore Mississippi Avenue

Mississippi Avenue is a lively corridor located within the Boise neighborhood, a colorful residential area chock-full of interesting shops and great restaurants. The businesses in this neighborhood clearly cater to the whims of millennials.

You’ll find beautiful plant nurseries, music venues, food cart pods, fantastic breweries (some of the best in Portland) and plenty of great clothing stores. For a deeper dive, read: 10 Best Things to Do on Mississippi Avenue.

Local’s Recommendation: Enjoy a meal at Lovely’s Fifty-Fifty. Dangerously delicious wood-fired pizza served alongside homemade ice cream. The secret to their award-winning pizzas? The sourdough starter.

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Afternoon: Two Options to Choose From

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Option A: Hike Forest Park

Portlanders take outdoor recreation seriously and nowhere is this more evident than the busy trailheads at Forest Park. Covering more than 5,200 acres, Forest Park is one of the largest urban forests in the country. With more than 70+ miles of trails, you’re bound to find a trail you love.

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Tour Pittock Mansion

Spanning 16,000 square feet and sitting pretty within the confines of Forest Park, Pittock Mansion is a stunning French-Renaissance mansion that dates back to 1914. This iconic Portland attraction boasts 46 elaborate rooms and was built so well that the even the original elevator is operational to this day.

Visitors can tour the home, an experience I recommend because you can see the original furniture from the time period and learn more about the lives of the family that lived here. The mansion is especially remarkable during the holidays because it’s fully decked out with elaborate decorations and tons of Christmas trees.

If you’re pressed for time and decide not to tour the mansion, at least make sure to head to the overlook behind the mansion for unparalleled views of downtown Portland. Catching the sunset from here is a must during your one day in Portland!

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Option B: Find the Witch’s Castle

The Witch’s Castle is the most popular hike in Forest Park and can easily be reached from Pittock Mansion. You might be asking yourself what can be so haunting about an abandoned structure in the middle of a forest?

Well, it’s an age-old tale of murder and haunt surrounds the Witch’s Castle and makes a visit to this structure all the more interesting. The gist is this: an angry father murdered his daughter’s husband because they got married without his consent (intrigued? You can read more here).

Ask any Portlander and they will tell you that hiking to the Witch’s Castle is a rite of passage. It feels as much a part of the city as the the Keep Portland Weird motto, which is why you simply can’t miss it during your 1 day in Portland.

Further Reading: Visiting the Witch’s Castle in Portland, Oregon

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Evening: Head to the Central Eastside

From delicious food, tons of charming boutiques and some of the best murals the city has to offer, exploring the Alberta Arts District during your 1 day in Portland is non-negotiable.

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Have dinner at Bollywood Theater

A super hip Indian restaurant with delicious fare. We visited with a group of friends for a birthday celebration and tried about 15 small plates – all were big hits! Plus, the atmosphere is great, especially for groups.

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Great Notion Brewery

Great Notion was born when three neighbors, drawn together by a common passion for home-brewing, decided to pursue their passion full time. The result? One of the best breweries in Portland.

Experimentation and creativity is the name of the game at Great Notion and the City of Roses is better for it. Try the renowned fruit beers, sours and hazy IPAs to see what all the fuss is about.

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Explore the Kennedy School

Only in Portland, right?

Swing by the Kennedy School to see what happens when you convert a school into a hang out spot for the neighborhood (the detention room was converted into a bar).

Old classrooms were reconstructed into hotel rooms, the detention room is now a bar and the Boiler Room a restaurant. Oh, what’s more, the gymnasium was converted to a cozy movie theater that plays re-runs.

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Option B: Explore the Hawthorn District Instead

The Hawthorne District spans 43 blocks and exudes an easy-going artsy vibe. The quirkiness and laid back nature of this area is irresistible to Portlanders. If you’re looking to shed some light on why people love living in Portland, I recommend exploring this area.

Wander down Belmont Street

The crown jewel of the Hawthorne District is Belmont Street, where you’ll find a high concentration of interesting shops, phenomenal restaurants, quaint cafes, vintage clothing stores and lively bars.

Food Cart Hop

My favorite thing about Portland’s robust food scene is the lack of pretension. Turns out you can have a great meal without a white table cloth, who knew!

Pop over to the famous food cart pods off of Hawthorne (called the Hawthorne Asylum Pod) during your 1 day in Portland. Food trucks aren’t just for tourists. Most of my coworkers rush over during the busy lunch hour, so you’ll be acting more like a local than a tourist with this activity.

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Tips for Visiting Portland

Best time to visit:

• Portland tends to have mild weather year round but I’d argue that the best time to visit Portland is between May and October. The weather is comfortable (even during summer because there’s practically no humidity) and chance of rainfall is minimal.
• If you can, try to time your visit with the vibrant spring season so that you can experience the cherry blossoms in full bloom or the breathtaking fall season when the city is ablaze with deep shades of orange, red and yellow.

Transportation:

• No Need to Rent a Car: Portland boasts an efficient public transit system called TriMet, encompassing buses, the MAX light rail, and streetcars, making it convenient to navigate the city without a car.
• Walkability: The downtown core, including areas like the Pearl District and Northwest Portland, is highly walkable. However, reaching neighborhoods on the east side of the Willamette River may require using rideshare services like Lyft or Uber.​

Weather:

• Always Carry a Rain Jacket: Portland’s weather can be unpredictable, especially outside the summer months. Rain is often light but frequent, so a reliable rain jacket is advisable.​

Safety and Awareness:

• Visible Homeless Population: Like many major cities, Portland has a visible homeless community. While levels of violent crime are low, property crime can occur. It’s advisable to avoid leaving valuables in plain sight in vehicles and to exercise general awareness.​

By keeping these tips in mind, you’ll be well-prepared to explore and enjoy all that Portland has to offer.

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Cheers!

Antonina