Post Overview: A Helpful Itinerary for 3 Days in Portland, Oregon
Portland, Oregon is my hometown and I know the city like the back of my hand. I love living here and take great pride in showing the city to visiting family and friends (every family has a designated tour guide, right?).
Seeing how most of my friends spend 3 days in Portland, I thought it might be helpful to share the exact Portland itinerary I personally share with my loved ones.
Growing up in Portland has left a lasting impression on me and I have sentimental feelings for the city. If you accused me of being bias, you’d be right. But listen, I’m hardly the only one to fall for the Rose City’s charm.
Portland has become a celebrity of sorts in recent years, especially in “hipster” circles. The city has seen a massive influx of new comers over the past five years, and I say welcome!
Hard to blame anyone for wanting to live here, the city is a gem. I mean, I’m still stumbling upon new and exciting things and I’ve lived here my whole life!
Without further ado, let’s talk about the best way to spend 3 days in Portland, from a local’s perspective.
Note for you, dear reader: If anything in this post doesn’t make sense or if you have any questions let me know in the comments below. I want your 3 days in Portland to be enjoyable and I’m here to help make that happen, so don’t hesitate to reach out. I love hearing from you!
Is 3 days in Portland enough time?
The honest answer is no, but it’s better than nothing and we’ll take what we can get.
Spending 3 days in Portland will give you a great introduction to the city, but it’s not enough time to absorb everything, especially if you want to take advantage of the nature scene Portland is known for. To that end, go easy on yourself because you’ll see a lot of things but you won’t see everything.
Portland is large, the city is comprised of six quadrants: North, Northeast, Northwest, South, Southeast and Southwest and this Portland itinerary will cover the most popular areas.
Who is this 3 day Portland itinerary for?
This helpful guide is for first time visitors planning to spend 3 days in Portland. The guide will cover everything from Portland’s top attractions and restaurants to local gems.
A long weekend in Portland, when done properly, will give you a robust feel for Portland while giving you reason to return for more.
Who am I and why should you trust me?
Don’t worry, I don’t offend easily and this is a fair question. 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’ll be sharing some of the most fascinating facts and lessons below.
How to spend 3 days in Portland Oregon
3 Days in Portland Itinerary ( Day 1 )
Focus Areas: The Pearl District, NW Portland & Mississippi Avenue
Start your day in the Pearl District
Portland’s trendy Pearl District is best described as industrial chic. Towering high rises (with rent prices to match, mind you) have cropped up around beautiful red-brick buildings — two worlds blending together seamlessly.
This Portland neighborhood is popular among locals thanks to the plethora of independent boutiques, modern cafes, cozy bars and charming galleries. Originally home to factories and loading docks, the Pearl has recently reinvented itself and is eager to show off.
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.
Grab a coffee from Sisters Coffee or Barista to start your day right.
Visit the largest independent bookstore in the world
Located within the Pearl District and spanning an entire city block, Powell’s Books is the largest independent bookstore in the world. Reason alone to visit during your 3 days in Portland!
Home to more than one million new and used books, the store covers 4 floors. If that sounds overwhelming, grab a map before embarking on the adventure. Arrive early or be prepared for crowds, Powell’s is one of the most visited places in Portland.
Local’s Tip: Pop into the Gold Room during your visit to see the rarest books in the store. 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.
Pop over to NW Portland
From Powell’s Books, head a few blocks west to start exploring my favorite neighborhood in Portland, NW Portland.
NW Portland is a pretty tree-lined residential neighborhood peppered with smalls shops and great restaurants. This is the neighborhood I’ve lived in the longest because of it’s charm, walk-ability and access to everything I need (grocery stores, entertainment and parks).
The best way to explore NW Portland is to wander through the neighborhood on foot. Stroll down 23rd Avenue and check out the shops that line this popular shopping street, often called “trendy third.”
Also, you might notice that a lot of the streets in NW Portland seem familiar and there’s a reason for it. The creator of The Simpsons, Matt Groening, grew up near NW Portland and named a handful of Simpsons characters after Portland streets.
Ken’s Bakery is my favorite bakery in Portland and the fact that I live on the same block as Ken’s is dangerous. Order the Oregon croissant if you have a sweet tooth or the leek croissant if you’re in the mood for something savory and you’ll see what all the fuss is about.
The quality of Ken’s baked goods is hard to beat, but that’s hardly a surprise considering the owner is a recipient of the prestigious James Beard Award.
It’s no secret that Portland is one of the best beer cities in the country and you’ll want to visit some of the big names during your 3 days in Portland. From a local’s perspective, no brewery shines brighter than Breakside Brewery — largely thanks to the plethora of awards and accolades bestowed upon it.
The prestigious awards span continents and there’s simply too many to list, but the Gold Medal at the Great American Beer Festival is worth mention. Expect long lines, this brewery is popular among both locals and tourists.
Salt & Straw
Salt & Straw has amassed a cult-like following since opening in 2011 and the steadfast devotion is justified — they churn out the best ice cream in Portland. Locally sourced seasonal ingredients take center stage and the innovative (albeit unusual) seasonal flavors warrant a sample or two.
Local’s Tip: Don’t skip the honey-lavender flavor, it’s the best.
If you have an insatiable sweet tooth (raises hand*) make a beeline toward Papa Haydn. The triple chocolate cake and carrot cake are dream worthy. I wouldn’t necessary recommend visiting Papa Haydn for food, but the desserts are worth inclusion on any decent Portland itinerary. I come here whenever I have cause for celebration and treat myself to a birthday cake from here every year without fail.
Walk over to Washington Park
Washington Park is often considered the crown jewel of Portland’s robust park system and it’s not hard to see why. Located on the border of the NW neighborhood, this breathtaking park spans 400 acres and houses six important cultural institutions — the International Rose Test Garden, the Portland Japanese Garden, the Oregon Zoo, Hoyt Arboretum, Portland Children’s Museum and the World Forestry Center.
Visit 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 and nowhere is this more evident than at the exceptional Portland International Rose Test Garden (better known as the Portland Rose Garden), which is located within Washington Park.
Portland’s beloved rose garden is both the largest rose garden in America and the oldest. Home to an impressive 650+ varieties of roses and more than 10,000+ bushes, it’s easily one of the best free things to do during your 3 days in Portland.
The history of the rose garden is equally fascinating. Originally started in 1915 by Jesse Currey, (an Oregon Journal editor and rose hobbyist), the rose garden was created in an effort to preserve roses susceptible to eradication during World War I.
Location: 400 SW Kingston Ave, Portland, OR 97205
Further Reading: Visiting the Portland Rose Garden (Local’s Guide)
Portland Japanese Garden
Opened in 1967, the perfectly-curated Portland Japanese Garden provides a calming escape from the hustle and bustle of city living. So if you find yourself overwhelmed by concrete, head this way.
The Portland Japanese Garden is regarded as one of the most authentic Japanese gardens in America, which is reason alone to visit during your 3 days 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 matcha or tea for a little break, you won’t be disappointed.
Image courtesy of the Portland Japanese Garden
Explore 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.
Tour Pittock Mansion
Spanning an impressive 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.
The tours are really cool because you can see the original furniture from the time period and learn more about the family that called it home (these folks were loaded). Commissioned by the publisher of the Oregonian, Henry Pittock, no expenses spared, the house was built so well that even the original elevator is operational to this day.
The Christmas season is especially remarkable because the mansion is decorated in the most elaborate manner with 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 sunset from here is a must during your three days in Portland!
Then hike to the Witch’s Castle
The Witch’s Castle is arguably the most popular short hikes in Forest Park and you can easily reach it 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 3 days in Portland.
Further Reading: Visiting the Witch’s Castle in Portland, Oregon
Explore Mississippi Avenue
After you’ve stretched your legs, head over to Mississippi Avenue and reward yourself with a delicious brew.
Mississippi Avenue is a lively corridor located within the Boise neighborhood, a colorful residential neighborhood chock full of interesting shops and great restaurants.
The business in this area 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.
Catch a show at Mississippi Studios
Check the roster at Mississippi Studios and try to grab tickets for a show. Catching a live performance should be a priority during your 3 days in Portland and Mississippi Studios is sure to fit the bill.
Food Option A: ¿Por Qué No? Taqueria
¿Por Qué No? Taqueria serves up the best tacos and guacamole in Portland, and the long lines prove it. Their margaritas also hit the spot, so if you’re craving great Mexican food during your 3 days in Portland, look no further. Swing by during Happy Hour (Monday-Friday from 2:30-5pm) for $1 off sangria, margaritas and cocktails, or visit on Taco Tuesday when the taco menu is 10% off.
Food Option B: Lovely’s Fifty-fifty
Dangerously delicious wood-fired pizza served alongside homemade ice cream. This beloved Portland restaurant was welcome with open arms when they first opened and it’s hard to imagine Mississippi without it. The secret to their award-winning pizzas? The sourdough starter.
Visit Stormbreaker Brewing
Stormbreaker is a crowd-favorite among local Portlanders for their hoppy IPAs, memorable ciders and great outdoor seating. Founded in 2013, this beloved Portland brewery now boasts two lively locations but I’m partial to the Mississippi location. Enjoy a cold glass of cider or an IPA with traditional pub fare (the nachos are worth mention).
3 Days in Portland Itinerary (Day 2)
Focus Areas: NE & SE Portland
Start your day in the Alberta Arts District
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 long weekend in Portland is non-negotiable. So let’s start day 2 of this Portland itinerary with brunch in Alberta.
Brunch at Proud Mary Cafe
Proud Mary Cafe hails from Melbourne, Australia where it cultivated a cult following before expanding to America with an outpost in Portland. It was love at first sight, this epic Portland brunch spot fills to the brim with eager locals and tourists every day of the week.
With only 3 days in Portland, you can’t afford to eat forgettable food, which is why I recommend starting your day at Proud Mary Cafe.
Plus, the coffee is hard to beat. The food is delicious and equally photogenic, they clearly know their target audience (ahem, millennials) and have the rave reviews to prove it.
Insider Tip: The ricotta pancakes are a must order.
Further Reading: 30+ Portland Brunch Spots Worth the (Inevitable) Wait
(Or) Pine State Biscuits
Let’s get real, it’s rare to find locals and visitors congregating in the same restaurants nowadays. Another clear exception is Pine State Biscuits where anyone is eager to wait in line for an hour when needed for the best biscuits in Portland, and that means something.
Swing by during brunch for knock-out breakfast sandwiches and you’ll instantly see why locals love this place so much — it’s definitely worth the hype.
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.
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. Pop in during your three days in Portland and see for yourself if Portland’s reputation as a foodie haven is warranted.
Visit the Kennedy School
Swing by the Kennedy School to see what happens when you convert a school into a hang out spot for the neighborhood.
Old classrooms were repurposed as hotel rooms, the detention room is now a bar and the Boiler Room is a lively restaurant. Oh, what’s more, the gymnasium was converted to a cozy movie theater that plays movie re-runs of classics, check the schedule here.
Partake in Alberta’s most popular event: Last Thursday
If you’re visiting Alberta Arts District during the summer months, makes sure to check out the Last Thursday Art Walk where local vendors, artists, performers and musicians share their craft along Northeast Alberta Street.
Head over to Mt. Tabor
The Mt. Tabor neighborhood is best known for beautiful bungalows, tree-lined streets and an overall neighborhood feeling that has you wondering if you’ve accidentally stepping onto a movie set.
Mt. Tabor Park
Undoubtedly, the star of the show in this lovely neighborhood is Mt. Tabor Park. Sitting atop an (extinct) volcano, this popular park offers some of the best views of Portland. It’s a great spot to bike, hike or simply enjoy a sunset picnic amidst locals.
Get your heart pumping by hiking to the top of the water reservoir before plopping down with your picnic basket and best friend in tow for a relaxing evening.
Next, head over to the Hawthorn District
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 3 days 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.
3 Days in Portland Itinerary | Day 3
Focus Areas: The Columbia River Gorge & Downtown Portland
Drive out to the Columbia River Gorge
Portland is known for spectacular scenery and unparalleled access to nature, so why not take a day trip to the breathtaking Columbia Gorge and see what all the fuss is about?
In terms of best day trips from Portland, it doesn’t get better than this, which is exactly why you should make an effort to see the Columbia Gorge during your long weekend in Portland.
The Columbia Gorge is a study in contrast. From alpine meadows and jaw-dropping waterfalls to desert landscapes and tepid rain forests, there’s something for everyone.
The best way to explore the Columbia Gorge is by car and trail. Take the Historic Columbia River Highway, known as the “King of Roads” was the first scenic highway in America to be designated as a National Historic Landmark.
Less than a one-hour drive from the city, the Columbia River Gorge makes for a great day trip from Portland even if you only have half a day to spare. So add this to your 3 days in Portland itinerary.
Did you know: The Columbia River Gorge is the largest National Scenic Area in the country.
Plunging a staggering 620 feet, Multnomah Falls is the tallest waterfall in Oregon. Nestled into the pristine Columbia River Gorge, an area with an abundance of waterfalls, mountains and numerous striking vistas for public enjoyment, you will find one of the most visited sights in Oregon.
Tip: The parking lot fills up very quickly so make sure to come early. Also, don’t miss hiking to the overview bridge, it’s well worth the small effort.
Further Reading: 20 Wildly Beautiful Oregon Waterfalls Completely Worth the Hype (& Effort)
Enjoy the views in Hood River
We can’t talk about the best day trips from Portland without mentioning the quaint town of Hood River, Oregon. This charming town is a mecca for outdoor enthusiasts and relaxers all the same.
In many ways, taking trip to Hood River feels like escaping to the South of France. The greenery, enchanting valleys and blushing fruit trees have a way of transporting you back to simpler times.
If you’re looking to escape the bustle of city living, you need not look further than a day trip to Hood River.
This past summer, I spent most of my weekends trying new wineries in Hood River (Read: 18 Best Wineries in the Columbia River Gorge).
Long weekend in Portland Itinerary, day 3 afternoon: Explore Downtown Portland
Portland’s downtown core a vibrant community with interesting restaurants, great local shopping options, home to Pioneer Courthouse Square — lovingly referred to as Portland’s living room.
Spend some time aimlessly wandering the streets during your long weekend in Portland. Don’t forget to pop into the small shops you pass along the way, I especially enjoy MadeHere store — they have the cutest earrings!
Walk down Tom McCall Waterfront Park
Tom McCall Waterfront Park is named after Oregon’s revered governor. The park swells with locals during lunch hour and it’s inevitable that you’ll be dodging bikers, walkers, skateboarders and young couples walking hand-in-hand.
All this to say, this waterfront park is great for people watching.
Try to time your visit to the waterfront with the spring season 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 Tip: 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.
Visit the Portland Saturday Market
The Portland Saturday Market is a beloved arts and crafts market that has been operational since 1973 (one of the oldest in the country!). If you enjoy arts and crafts you may want to allocate a Saturday morning to this lively market during your 3 days in Portland.
Crafty locals sell everything from birdhouses to paintings, food, jewelry and musical instruments. Simply wander from one stall to the next, you never know what you’ll find.
Visit the PSU Farmers Market
Held every Saturday, rain or shine, the PSU Farmers Market is the best farmers market in Portland (in my humble opinion). Full of local farm-fresh veggies and fruits, stock up on ingredients and make yourself a home cooked meal!
There’s more than 200 stalls at this particular farmers market, so believe me when I tell you it’s big. Start by paying a visit to the breakfast burrito stall before perusing the various stalls, and whatever you do – don’t skip the chocolates at Honey Mama’s (I love the lavender flavor).
Keep Portland Weird mural
Omitting a visit to the Keep Portland Weird sign would be inexcusable in a proper Portland itinerary!
Is it kind of cheesy? Sure but don’t skip it unless you’re lactose intolerant (ugh, sorry about the bad pun, it’s just the worst).
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 3 days in Portland. So route yourself to this mural and let the magic happen.
The Keep Portland Weird sign has become synonymous with the city’s lifestyle and feels like a call to action for some folks. 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. The rest, as they say, is history.
Location: 22 SW 3rd Ave, Portland, OR 97204
See the second largest copper statue in America
Sitting pretty at nearly 35 feet, 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 so swing by while you’re exploring downtown during your long weekend in 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, and threatens 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.”
Further Reading: 20 Interesting Facts About Portland (You Might Not Know)
Image courtesy of Oregon Live
Alternative Portland Itinerary: Day Trips for 3 Days in Portland
If you’d like to venture beyond the (epic) Columbia Gorge during your 3 days in Portland, you might find the following day trips enjoyable.
Further Reading: 10 Adventurous Day Trips from Portland
Take a road trip to the Oregon Coast
Nothing screams Pacific Northwest like the striking Oregon coastline. A scenic 1.5-hour drive from Portland will lead you directly to the salty sea. If you’re pressed for time during your three days in Portland, make Cannon Beach your top priority.
My childhood is freckled with memories of summer at the Oregon coast, so I’m definitely biased. It took my husband a few visits to fall under the coast’s spell, but as soon as he discovered crabbing and clamming – he was hooked.
Cannon Beach is the most popular beach on the Oregon Coast and you may have seen photos of Haystack Rock without knowing its name. Taking a brisk stroll down the coast is a perfect way to escape the buzz of city living, I highly recommend.
Further Reading: 12+ Charming Oregon Coast Towns You Can’t Help But Love
Go on a winery tour in the Willamette Valley
Everyone knows that Oregon is an outdoor enthusiasts dream. The drastic (and diverse) natural landscapes can keep anyone entertained for years with miles of hiking trails and sweeping vistas.
But what’s the point in hiking without a proper reward afterwards? Well, Oregon has you covered in that department as well — in fact, Oregon is the 4th most wine producing state in the country.
And of all the notable wine regions in Oregon, none is more famous than Willamette Valley because it is home to 500+ wineries.
Sitting at the same latitude as France’s notable wine regions, Willamette Valley is known for producing knock-out award-winning Pinot Noirs that can hold their own in worldwide competitions.
Sipping a chilled glass of Chardonnay in the summer (or robust glass of award winning red in fall) is a perfect way to properly cap your 3 days in Portland.
Best time to visit Portland
By and large, Portland tends to have mild weather year round. The one season I would avoid is winter because the colder temperatures make exploring less enjoyable (although there’s plenty of cozy coffee shops to take cover in!).
To that end, the best time to spend a long weekend in 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.
Personally, my favorite seasons in Portland are fall (September/October) and spring (April/May).
Portland Itinerary Tips: Getting around Portland, Oregon
Biking is the number one way to get around Portland. In fact, Portland is rated the most bike-able city in America year after year. So grab a BIKETOWN bike to explore town.
Driving in the city is fairly easy (especially if you’re comfortable driving in cities) and parking is reasonable at $2/hour in the downtown metered area.
For longer stays, the City of Portland has 5 parking garages that charge the same rates as on-street parking ($2/hour or $13-$16 all day).
Public Transportation is easy to use and fairly inexpensive ($2.50 for two hours/$5 all day). In addition to the bus, Portland offers the MAX and Portland Streetcar.
Uber/Lyft/Taxi are operational in Portland and (based on personal experience) reasonably priced.
If driving in Portland, it’s important to know that pedestrians ALWAYS have the right of way — even if sidewalks are unmarked.
Best Coffee in Portland
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 here’s a few spots you should make an effort to visit during your 3 days in Portland, Oregon.
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.
Spella Cafe: Originally started as a food cart before finding a more permanent home in a tiny hole-in-the-wall, Spella Cafe will transport you to Italy instantly. So if you like old-school cafes with charming European, this is the spot for you.
Spella Caffe has mastered the craft of coffee. The cappuccinos are airy and light and we’ve never had a bitter taste from the properly-roasted beans. Local’s Tip: Their affogato (ice cream with espresso) is the best in Portland.
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.
Heart Coffee: Started by a married couple that began roasting beans out of their home, Heart Coffee has a cult following in Portland thanks to their delicious high-quality coffee and Instagram-worthy interiors.
You’ll find folks ardently consumed by laptop screens, coworkers discussing deadlines and excited out-of-towners with cell phones in hand. One thing is guaranteed, everyone will leave happy because even the simplest drink is bound to impress at this great Portland cafe.
Further Reading: 15 Charming Portland Cafes You Can’t Help But Love
Great (fancy) restaurants to add to your Portland Itinerary
Paley’s Place: Pacific Northwest bistro fare/french cuisine served in a beautiful victorian home. We go to Paley’s for special occasions like our wedding anniversary.
Jaqueline: Delicious seafood curated into beautiful and creative dishes. Get the tasting menu here, it runs $60 per person for 8 courses. In the world of tasting menus, it’s not a bad deal. I came here twice in one month after discovering it.
Ava Genes: Fresh, farm to table Italian-inspired cuisine. The chef, Joshua McFadden authored a James Beard Award winning cookbook titled Six Seasons: A New Way with Vegetables. A book I cannot recommend enough, especially the mushroom recipes.
Le Pigeon: French-inspired cuisine serving delightful dishes at communal tables. Reservations required and often book out weeks, sometimes months, in advance.
Coquine: Casual cafe by day and farm to table American cuisine by night. Make sure to cap your meal with their famous chocolate chip cookie.
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Where to stay during your 3 days in Portland
I suggest staying in the downtown core during your long weekend in Portland because it’s well connected by public transportation. There’s plenty of hotels in the area, plus you’ll be close to great restaurants, bars and entertainment.
But honestly, it’s hard to go wrong with any of the charming Portland neighborhoods.
My two top centrally-located hotel recommendations in the downtown area are:
The Nines Hotel: Swanky special occasion hotel a stone’s throw from Pioneer Square. Whenever celebrities or athletes come to town, this is where they stay.
Hotel Woodlark: New to the scene but makes quite an appearance. The lobby of this cute boutique hotel is home to Good Coffee, making it easy to start your day right.
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Long weekend in Portland (Post Summary)
We covered a lot of ground during your 3 days in Portland! I hope you found this long weekend in Portland itinerary helpful, don’t hesitate to reach out with questions!
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That’s a hell of an itinerary. I hope you had time to take a rest.
Another great restaurant to try is Interurban in the mississippi neghtborhood.