Post Overview: Portland Date Ideas | Romantic Things to Do in Portland, Oregon
As a lifelong local, I’ve had my fair share of Portland dates (some good, some ugly). Thankfully, there’s a plethora of romantic things to do in Portland if you know where to look. But in true Portland fashion, there’s typically a unique twist every now and then.
One of my friends just recently re-entered the dating scene so the two of us sat down and brainstormed the best Portland date ideas. We shared stores of fun dates in Portland and highlighted some of our favorite romantic things to do in PDX.
I thought it would be fun to share the list with other locals in the hopes of making your planning easier. I hope you enjoy!
Portland Date Ideas | Romantic Things to Do in Portland, Oregon
Enjoy a memorable meal at Le Pigeon
Ask any Portlander about the most memorable meals in Portland and the honest ones will mention Le Pigeon first, the dishonest ones will keep it a secret. Opened in 2006 by (then 25-year old) Chef Gabriel Rucker, Le Pigeon is credited for single-handedly putting Portland on the national culinary map. I’m not exaggerating.
Since opening, the restaurant garnered praise from food critics and notable chefs across the nation. Naturally, Chef Rucker pocketed not one, but two prestigious James Beard awards. To this day, serious foodies make pilgrimages to Portland specifically for this gem.
Why is the tasting menu experience one of most romantic things to do in Portland? Well, it’s all about the food.
Le Pigeon focuses on seasonal French-inspired cuisine using ingredients sourced from the bounty of the Pacific Northwest. Offering two exceptional 5-course tasting menus (one for vegetarians) in a relaxed setting, I recommend opting for the brilliant wine pairing to cap off your experience.
The attentive waitstaff are eager to share their knowledge to ensure you get the most from your evening. The entire tasting menu affair feels inviting and approachable, largely thanks to the pretension-free service. The hours slip by (especially after the wine sets in) and you’ll find yourself adding this experience to your rotating list of best date ideas in Portland.
Check out the famous penny at the Portland Historical Society
Here’s a fun fact you may (or may not yet) know. The founders of Portland, Oregon were two settlers from New England. One from Boston, Massachusetts and the other from Portland, Maine.
Both settlers wanted to name the city after their respective home towns and decided to settle for a coin toss. And that is how Portland, Oregon got its name.
If you’re looking for unique date ideas in Portland, I suggest swinging by the Portland Historical Society to see the 1845 penny used to decide Portland’s name.
Visit the Portland Japanese Garden
Opened in 1967, the perfectly-curated Portland Japanese Garden provides a calming escape from the hustle and bustle of city living and the Portland cherry blossoms during spring make the experience that much better.
Few know that Portland’s Japanese Garden is often referred to as one of the most authentic Japanese gardens outside of Japan. After visiting Japan myself, I can attest that this Japanese Garden is in fact quite impressive.
The garden has something beautiful to offer every season of the year, but there’s something exceptionally beautiful about spring and fall, which is why the garden swells with locals and tourists alike during those two seasons.
- Admission: Advanced ticket reservations required and can be booked online.
Local’s Tip: Make sure to check out the cozy Umami Cafe for matcha or order any of the tea on the menu, you won’t be disappointed. It’s one of the most romantic things to do in Portland!
Have a staycation at McMenamins Edgefield
Admittedly this isn’t a first date idea in Portland, but would be a great option for an anniversary or special occasion.
McMenamins Edgefield is a 74-acre property sitting atop a former poor farm a mere 20-minutes from downtown Portland.
The property was abandoned and neglected when the practice of poor farms was deemed inappropriate. The McMenamin brothers (famous for rehabilitating historical properties in Oregon and Washington) bought the property in the 1990’s and took on the arduous task of transforming it into a whimsical place for the people of Portland to enjoy.
Take your time strolling through the gardens and enjoy the sweeping scenery. You’re welcome to stroll the entire estate with wine or beer in hand — plus, the artwork really pops after a few glasses! With so many activities to choose from, his is easily one of the most romantic things to do in Portland.
The history alone is what makes this one of the best date ideas in Portland. If you’re visiting during the summer months try to catch a concert in the great lawn — they’re known for hosting big names!
Catch a live show at Mississippi Studios
Mississippi Studios is a recording studio and music venue in the Boise neighborhood. Best known for the easy-going vibe, great brews, heated outdoor patio and cozy spot to catch a live show, this is the place to be on a weekend evening.
So check the roster at Mississippi Studios and try to grab tickets to a show — catching a live music performance is one of the best date ideas Portland and Mississippi Studios doesn’t disappoint.
I once saw Marty O’Reilly & the Old Soul Orchestra and the memories still give me goosebumps. The venue is so cozy and intimate.
Have a picnic in 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 Rose Garden within Washington Park, which is usually in bloom from May to October.
Portland’s beloved rose garden is the largest and oldest rose garden in America, which makes paying a visit and obvious Portland date idea. Home to an impressive 650+ varieties of roses and more than 10,000+ bushes, it’s easily one of the best free and romantic things to do 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.
You don’t have to be a rose-enthusiast to appreciate this beautiful garden, or to realize this is one of the most romantic things to do in Portland.
Spend an evening at Enso Winery
Any Portland wine bar serving pours out of a garage-inspired space deserves to be on a list of unique date night ideas in Portland. Following the lead of many great names before them (Apple, Google and Disney, to name a few), Enso Winery opened its (garage) doors to the public Memorial Day 2011 and hasn’t slowed since.
Focusing on quality over quantity, the folks behind Enso Winery hand craft old-world style wines using grapes sourced from Vineyards in Washington, California and Oregon. They produce around 1,000 cases of small-batch wine per year (all within city limits!) and the passion shows.
The mastermind behind the operation is Ryan Sharp. Trained on the sunny banks of Willamette River, Sharp pursued an ambitious goal: produce world-class wines in the heart of Portland. Thankfully, for the benefit of all thirsty Portlanders, he succeeded.
The wines produced at this charming Portland wine bar aren’t distributed commercially, so the only way to get your hands on them is to visit the winery. And let’s be honest, watching the hours slip by at a winery is one of the best date ideas in Portland.
Expect to find refreshing classics like Grüner Veltliner and the (beloved) Mourvèdre alongside full-bodied reds like Cabernet Franc. The wine pairs perfectly with the generous charcuterie boards offered (made with locals meats and cheeses) and the divine chocolates.
If you’re coming to this Portland wine bar with a die-hard beer fan, fret not. The menu includes local northwest beers and ciders as well to ensure that everyone leaves happy.
Catch sunset at Pittock Mansion
Touring Pittock Mansion is yet another cool Portland date idea if you like history (or just looking at rich people’s stuff). Pittock Mansion is a stunning French-Renaissance style mansion that sits atop the West Hills and spans 16,000 square feet, boasts 46 elaborate rooms and is open to the public.
The house 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 lives of the family that built it.
The Christmas season is especially remarkable because the mansion is decorated in the most elaborate manner with tons of Christmas trees. I’ve lost count of the number of times I’ve visited Pittock Mansion during the holiday season and still consider it one of the best date ideas in Portland.
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.
Local’s Tip: Pittock Mansion has the best viewpoint in Portland, believe me, I spent a month searching for the best views in Portland and this comes in at #1. Those in search of the most romantic things to do in Portland, can’t afford to miss these sunset views.
Enjoy brunch at Proud Mary Cafe and stroll Alberta Street
Proud Mary Cafe hails from Melbourne, Australia where it cultivated a cult following before deciding to expand to America by opening a small restaurant in Portland, Oregon.
The result? An overnight success. Proud Mary Cafe fills to the brim with eager locals and tourists alike every weekend morning, everyone excited to get their hands on the brunch menu. 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. My personal favorite items on the menu include the avocado toast, potato hash and the cakey ricotta pancakes (which are unlike any pancakes I’ve every had before).
Grab evening drinks at Multnomah Whiskey Library
Is the Multnomah Whiskey Library pretentious? Absolutely. But it’s classy too. Plus, it’s a proven fact that alcohol dissolves uneasiness and awkwardness which makes this one of the best Portland date ideas.
If your knowledge of whiskey expands beyond the aisles of Fred Meyer then you’re in for a treat. This locale will make you feel like a baron from a bygone era.
The sophisticated interior — clad with dark leather furniture, bookshelves storing 1,000 whiskey bottles and classy music — clearly evokes library feels. But rather than Nabokov and Dickens lining the shelf, you’ll find the knowledgeable team scrolling past Ardbeg and Lagavulin.
Getting reservations at Multnomah Whiskey Library feels like an impossible task. This is one of the best bars in Portland and everyone knows it. I mean, they create the best Old Fashioned in Portland, Oregon, so a wait is all but guaranteed.
So while I can’t guarantee you’ll get a table, I can guarantee this is one of the most romantic things to do in Portland.
You may enjoy reading: 10 High-Spirited Portland Cocktail Bars You Won’t Soon Forget
Go brewery hopping
There’s no denying that Portland has clearly become the epicenter of a booming craft brew community. Home to nearly 70 breweries, one thing is certain – there’s no shortage of great breweries in Portland to choose from.
I recently rounded up the best breweries in Portland for anyone interested. But if you’re short on time, I suggest Gigantic Brewing, because it’s one of my favorites (especially if you love IPAs).
Seriously, I would drive one hour out of the way for the IPAs at this epic Portland brewery. Consistently serving up great beer in a casual atmosphere, Gigantic Brewing is one of the best places to take a date in Portland.
Nothing fussy, just a relaxed venue with stellar brews. What more could you ask for?
Dessert at Papa Haydn & stroll down 23rd Avenue
The triple chocolate cake and carrot cake are sublime! I wouldn’t necessary recommend visiting Papa Haydn for food, but the deserts are worth a visit! I come here for celebratory occasions with girlfriends or whenever I’m feeling the need for one of the most romantic date ideas in 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.”
I suggest taking a slow stroll down the avenue after you’ve had your fill of cake. If you’re still in the mood for something sweet, head two blocks down to Salt & Straw ice cream.
Catch sunset from Mt. Tabor
Catching sunset at Mt. Tabor Park is one of the best Portland date ideas. It’s hard to find a more romantic activity in Portland during the summer months. So pack your favorite picnic basket, or better yet, grab a pizza from Apizza Scholls (one of the best pizza places in Portland) and watch the sun fade over downtown Portland.
Experience the swifts at Chapman School (September)
A lot of folks don’t realize that Portland is home to one of the largest roosts of Vaux’s Swifts in the world. It’s true, so why not make a unique Portland date night out of it?
Like clockwork, every September, Portland’s Chapman Elementary is swarmed with locals eager to catch a glimpse of migrating Vaux’s Swifts as they fly into the school’s chimney by the thousands to nest for the night.
Portlanders make an entire event out of this incredible sight because it’s free and one of the most romantic things to do in Portland. Bring a picnic blanket or chairs and enjoy an evening of wander surrounded by friends or your special someone.
Enjoy a performance at the Oregon Symphony
I’ve seen a few performances by the Oregon Symphony and can tell you from firsthand experience — it doesn’t get better than this. An evening dressed in your finest clothes while being serenaded by classical music, this is definitely one of the most romantic things to do in Portland.
Of course, everyday attire is completely fine too (this is Portland after all), but if you need an excuse to dress up, this is it.
To check the roster (or purchase tickets) you can click here.
Catch a movie at the Kennedy School
This is one of my favorite date ideas in Portland. The Kennedy School is an abandoned school that has been converted into all sorts of fun.
The boiler room is now a restaurant, the gym is a movie theater and the detention room is a bar. I enjoy wandering the halls aimlessly and normally spend 2-3 hours exploring. Get boozy and slow the evening down with a plate of tempting tater tots before you.
Tip: You can actually stay at McMenamins Kennedy School because the classrooms were converted into hotel rooms. What’s more, guests get access to the soaking pool.
Get lost at Powell’s Books
Rated by CNN as one of the coolest bookstores in the world, Powell’s Books, dubbed City of Books, is the largest independently owned bookstore in the world – selling both new and used titles for all to enjoy.
Located within the Pearl District and spanning an entire city block, Powell’s Books is the largest independent bookstore in the world.
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, visiting Powell’s is by far one of the best date ideas 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 safely tucked between the pages. The price? $350,000.
Further Reading: Local’s Guide to Powell’s Books
Hike the Wahkeena Falls Trail
Located next to the most popular waterfall hike near Portland, Multnomah Falls, Wahkeena Falls is an often overlooked gem by most unassuming visitors. That’s not to say the hike is unpopular though!
This waterfall hike near Portland is popular amongst those in the know, so crowds are all but guaranteed during the warm summer months.
There’s two ways to experience Wahkeena Falls, either from a viewing platform near off the highway or by hiking up to see the roaring beauty of the entire three-tiered waterfall.
I would argue that this beautiful waterfall near Portland warrants the hiking effort, so strap on your boots and hit the trail. You’ll be rewarded with beautiful views of the falls from various points throughout the trail.
If you continue down the trail for three miles you’ll find yourself in front of another beauty — Fairy Falls.
Seeing both waterfalls would clock you in at a six mile hike, which is the perfect length and effort before hitting up your favorite Portland brewery.
Further Reading: 8 Epic Waterfalls Near Portland Worth the Drive
Romantic things to do in Portland | Portland Date Night Ideas (Post Overview)
In sum, here’s a quick roundup of the best date night ideas in Portland, Oregon.
- Enjoy a memorable meal at Le Pigeon
- Have a staycation at McMenamins Edgefield
- Check out the famous penny at the Portland Historical Society
- Visit the Portland Japanese Garden
- Catch a live show at Mississippi Studios
- Have a picnic in the Portland Rose Garden
- Spend an evening at Enso Winery
- Catch sunset at Pittock Mansion
- Brunch at Proud Mary Cafe and then stroll Alberta
- Grab evening drinks at Multnomah Whiskey Library
- Go brewery hopping
- Dessert at Papa Haydn & stroll down 23rd Avenue
- Catch sunset from Mt. Tabor
- Experience the swifts at Chapman School (September)
- Enjoy a performance at the Oregon Symphony
- Catch a movie at the Kennedy School
- Get lost at Powell’s Books
- Hike The Wahkeena Trail
Map of the most romantic things to do in Portland
Cheers!
What do you think?