30 Fun and Creative Date Ideas in Portland
You weren’t born yesterday. You already know that you can have a cup of coffee or go out for pizza on a date. In no particular order, here is my list of offbeat and less obvious date ideas in my home city, Portland, Oregon, to inspire your next night out. It would also work for friend outings, out-of-town visitors, and, in most cases, family excursions. Everything is within city limits and many things are free or cheap. To help with your Friday night brainstorming, here are fun and creative date suggestions in Portland.
1. See the Portland Troll
Great for: A date with a fairytale ending.
Season: Whenever it’s not pouring rain.
One of Portland’s newest attractions is a large and expressive troll named Ole Bolle. Since the summer of 2023, he has been living on the grounds of Fogelbo, a Swedish-style log house on the National Register of Historic Places. Stouthearted adventurers can find the 19-foot Ole Bolle investigating a cabin there. Whether he is more interested in the pastries or the human visitors inside is not entirely clear. There may be an opportunity for heroism as you defend your beloved from becoming a troll’s lunch. If you survive the encounter unscathed, head inside and reward yourselves with a Smörgåsbord at Broder Söder. Feel encouraged to mock your date’s pronunciation of the Scandanavian menu items, at least until it’s your turn to order.
2. Comedy in the Park
Great for: A cheap date that will get you laughing together.
Season: June - August
On Friday evenings in the summer, Kickstand Comedy hosts a free live comedy show at Laurelhurst Park, aptly called Comedy in the Park. Bring snacks and a blanket to enjoy a picnic dinner while hearing local comedians cracking jokes. While you’re in the park, look for the Laurelhurst ducks, a roving band of resident ducks in colors you didn’t know ducks could be, like iridescent purple. Meanwhile, the picturesque lake, the soft light of long summer evenings, giant trees, and blooming rhodendrons will keep things romantic.
3. Explore the Kennedy School
Boiler Room at the Kennedy School
Great for: Enjoying a trip to Detention for the first time.
Season: Any
Once an elementary school, the McMenamins Kennedy School has found new life as a hotel full of date night potential. Besides the courtyard restaurant, there is a movie theater, soaking pool, brewery, and multiple bars, including a cozy little cocktail lounge called Detention. You and your date can grab a beer to sip while you explore the grounds and swap stories about your glue-eating stage or your savant-like ability at the recorder. Look for many original features of the 1915 school, like chalkboards and cloakrooms, as well as some really weird art.
4. See a movie at the Living Room Theaters
Great for: A cozy date on a rainy night.
Season: Any
Of all the movie theaters in Portland, I’d say Living Room Theaters has the best setup for date nights. The theater is also a bar, so if you get nervous you’ll be late and end up arriving weirdly early, you can order a glass of wine and act like it was intentional. I heard a friend did that. Certainly not speaking from personal experience. The theater is small, but the movie selection is usually quite good, ranging from blockbusters to artsy conversation starters. Before the show, you can order salads, pizzas, and burgers to combine dinner and a movie. Try the couch seats to get cozy with your date during the film.
Alternatively, add some variety to the typical movie night by playing B-Movie Bingo at the Hollywood Theater. Grab a beer and pizza by the slice, then head to the theater to wait for the movie cliches to begin.
5. OMSI After Dark
Great for: Knowing that if your blind date turns out to be boring, you can still salvage the night by learning about science.
Season: Any
Want to see a cool dinosaur exhibit without getting a weird look from the 6-year-old you just pushed out of the way to reach it? Then, OMSI After Dark is for you. This 21+ event is a chance to roam around Portland’s science museum with a beer, your date, your friends, and a bunch of other childlike adults. Look for vendors, special exhibits, and demonstrations while you’re there. OMSI After Dark usually happens on the last Wednesday of the month. I’d suggest reserving tickets in advance. This one gets crowded!
6. Birdie Time
Great for: Double dates.
Season: Any
Keep your date night playful at Birdie Time, an indoor mini golf course and tap room. At $8 for a round of mini golf, it’s a fun, cheap date that can bring out your competitive side, or perhaps just your silly side. It is mini golf, after all. On the menu, look for over 30 craft beers, plus wine, cider, seltzer, non-alcoholic drinks, shareable appetizers, pizzas, and burgers. For couples who enjoy regular golf without colorful props (we’re way past my comfort zone now), try the golf simulator. I’ve seen movies. I know helping someone adjust their golf swing gets flirty fast.
7. See the blooms at the Rose Garden
Great for: Reciting a sonnet to your beloved in the Shakespeare Garden.
Season: Potentially any, but the roses bloom from around late May until October. Peak bloom is in June.
Shakespeare knew it. Brontë knew it. Roses are the most romantic flower. With over 10,000 rose bushes in every color imaginable, it’s hard to think of a place with a better atmosphere than Portland’s International Rose Test Garden. As you and your date wander through rows of blooms, look for new types of roses, prize-winning roses, and a section devoted to miniature roses. One of my favorite spots is the Shakespeare Garden, a corner of the Rose Garden with plants mentioned in Shakespeare’s works. You can also find sculptures, a grassy amphitheater perfect for picnicking, a gift shop, and views of Mt Hood and the Portland skyline as you stroll.
8. Cathedral Park
Great for: A date your dog can come on.
Season: Best spring through fall.
Fresh take, Cathedral Park is the most romantic park in Portland. While it doesn’t have the splendor of thousands of blooming rose bushes, the arches of the St John’s Bridge provide more than enough ambiance. True to the name, when sunlight hits the bridge on summer evenings, you’ll feel like you’re in an outdoor cathedral. Stroll along the Columbia River, then picnic on the grassy lawn. If you head north, you’ll see the big ol’ Love sign that is the cover photo for this article. Cathedral Park is also within walking distance of downtown St John’s. Head up the hill to have wine at 45th Parallel, coffee at Sparrow Bakery, or a beer pretty much anywhere.
9. Visit the Freakybuttrue Peculiarium and Museum
Great for: An early date, like the third one. You’ve already done drinks and dinner and want to shake it up with an autopsy.
Season: Any
When I visited the Freakybuttrue Peculiarium and Museum, the only other visitors there were a couple on a date. They helped me understand its full potential. While I was quietly enjoying myself browsing the oddities, they were getting teary-eyed from laughing so hard. I get it. As a museum of the strange and obscure, everything in there is a perfect conservation starter and future inside joke. I know tastes differ, but if I went on a date to the Peculiarium and we weren’t laughing together by the end, I would have concerns. Aliens do an autopsy on you in there, it deserves a reaction.
10. Go rock climbing
Circuit Gym
Great for: A date that is also a workout, how efficient! Oh, and romantic. Mostly romantic.
Season: Any
Finding a sporty date in Portland can be hard, especially on a rainy day. When you and your person are feeling restless, consider heading to an indoor climbing gym for a great workout that feels like being on a playground for adults. If you know what you’re doing, top-roping will quickly build trust between two people as one gently lowers the other from the ceiling back down to earth. If you’re new to climbing, take a short intro class to learn to belay or avoid the ropes altogether and stick with bouldering. The Circuit Gym is a dedicated bouldering gym with routes for every skill level.
11. Hear live music
The George Colligan Quartet at The 1905
Great for: Making sure you and your date will be able to agree on a road trip playlist.
Season: Any
If you don’t want to join the teeming hordes at the Moda Center, Portland’s smaller live music venues are fun and relaxed date night destinations.
Portland’s coziest music venue is The 1905 jazz club. The chairs are arranged side by side so you and your date can get close while watching the show. The drink menu comes in strong with an eclectic wine list and creative cocktails. Food options range from tempting snacks like garlic knots and pizza by the slice to pasta dishes.
Check out Alberta Street Pub for a laidback place to enjoy live music with a craft cocktail. In the summer, the covered patio is a treat.
For an intimate venue that feels like a Prohibition-era jazz club, head to the Jack London Review.
To dance to live music, try out the Goodfoot.
Reopening in the spring of 2024, it’s hard to beat the log cabin ambiance of the Doug Fir Lounge.
Billed as the musician’s music venue, Mississippi Studios is a Portland classic where everything from the walls to the stage is custom-designed to make the listening experience exceptional.
For a chance to dress up, see the Oregon Symphony at the Arlene Schnitzer Concert Hall.
12. Sing karaoke
The Spare Room
Great for: Breaking out of your shell.
Season: Any
Belting out your unique rendition of Thong Song or Tiptoe Through the Tulips is guaranteed to wow your date. Here is where to do it in Portland:
For a casual and welcoming scene, try karaoke at the Spare Room.
To have a drink with a tiny umbrella in it before your performance, head to the Alibi Tiki Lounge.
For an old-school Portland karaoke night that includes Chinese food, check out Chopsticks.
If you have a way cooler karaoke song than mine, show it off at the Baby Ketten Club.
13. Bar trivia
Steeplejack Brewing hosts weekly trivia nights
Great for: Dates where your friends come along.
Season: Any
Sometimes date nights can be the most fun when they include the whole crew. For your double dates, triple dates, or just spending time with your friends, try out a trivia night to show off your arcane knowledge that has been useless in all other settings. For schedules and locations, check out organizer websites like Geeks Who Drink, Last Call Trivia, or Bridgetown Trivia.
14. Go wine tasting
The wine shop Vino has tastings events twice a month
Great for: Couples who have strong feelings about the differences between French and Slavonian oak. Or, for making sure your date doesn’t have strong feelings about French and Slavonian oak.
Season: Any
Here is one of my favorites. You drink a little wine, get a snack, and have a chat that may or may not relate to anything you’re drinking. As you can see from my article on the best wine bars in Portland, I have some thoughts on the subject. Briefly, look for flights at wine bars like Pairings Portland, Stem Wine Bar, Gilded Raccoon, ENSO Winery, and Vino Veritas. For great views and a full food menu, Noble Rot is a rare restaurant that offers wine flights. A great way to taste local wine without driving to Dundee is by checking out an urban tasting room in Portland like Erath, Battle Creek, or Helioterra.
15. Watch the sunset from Council Crest
Great for: A picnic involving charcuterie.
Season: Best in summer.
At over 1,000 feet in elevation, Council Crest is one of the highest points in Portland. The park at its summit has fantastic views of downtown and five Cascade peaks on a clear day: Mt Hood, Mt Adams, Mt St Helens, Mt Jefferson, and Mt Rainier. On summer evenings, the grassy lawn is a perfect place to roll out a blanket and enjoy a picnic dinner while watching the sunset. To add a challenge to the excursion, you can start at Marquam Nature Park and hike to the summit, just over 3 miles roundtrip. Or, you can drive to the top if your picnic basket is feeling heavy.
16. Find a speakeasy
Great for: Hatching plans that the feds can’t know about.
Season: Any
Want to feel like you’re getting away with something naughty while not actually doing anything illegal, immoral, or even impolite? Then head to a speakeasy with your date and pretend like it’s 100 years ago. If you dress as Bonnie and Clyde, you’ll fit right in at Bible Club, a Prohibition-era-themed bar in Sellwood with some of the best cocktails in Portland. Or, head down to the basement of the Hoxton to find the tucked-away speakeasy-style bar, 2NW5. More secrets to discuss? A nondescript staircase in Loyal Legion will take you to Voysey’s sumptuous interior. Just follow the red light.
17. Japanese Garden
Great for: Creating a feeling of harmony.
Season: Anytime that it’s not pouring rain.
The Japanese Garden is one of the best places in Portland to find a moment of calm away from the noise and bustle of the city. Known as one of the most authentic Japanese gardens outside of Japan, visiting can make you feel like you’re on the other side of the globe while still being on a Trimet route. As you and your date explore the meandering paths, look for sand gardens, elegant bridges, a wisteria arbor, a waterfall tumbling over mossy rocks, and a viewpoint overlooking Mt Hood. Head inside the Pavilion Gallery to see the rotating art exhibition. In April, an extraordinary 80-year-old weeping cherry blooms just outside the gallery. After seeing the garden, stop by the Umami Cafe for tea, snacks, and desserts.
18. Visit the Portland Art Museum
Great for: Lowkey scoping out if you and your date share a compatible sense of aesthetics.
Season: Any
Next time you’re feeling stuck inside on a rainy afternoon, grab your date and head to the Portland Art Museum. The museum’s permanent collection offers a little bit of everything, with exhibits ranging from Tang dynasty ceramics to contemporary art of the Northwest. If you’ve been before, rotating exhibits ensure there is something new to discover with each visit, whether about artifacts of Ancient Egypt or modern fashion design.
19. Find the Collins Beach UFO
Great for: Getting rid of your tan lines.
Season: Best in summer.
Sauvie Island is an excellent date destination for many reasons, one of the more unusual being the bizarre abandoned boat hull that looks like a technicolor UFO. As a fun curve ball, it’s on a clothing-optional beach. Whether or not you and your date feel comfortable enough with each other and the other beachgoers to bear it all, it’s a fun treasure hunt to find the UFO boat. Park by access point #3 and follow the trail to the beach. Once you reach the sand, follow the treeline south for a short distance until you see the boat. You can climb into and on top of it, but be aware that it’s in rough shape. If UFO boats and naked people aren’t your thing (you weirdo), try out one of the other best things to do on Sauvie Island, like looking for sandhill cranes, hiking, pumpkin patches, and fruit picking.
20. Do the elixir tasting at Raven’s Manor
Great for: Couples who think haunted houses should be open year-round.
Season: Any
Usually, it’s a bad sign when someone describes a date as creepy. Not so at Raven’s Manor, Portland’s haunted house-themed bar. From the gargoyles to the spooky portraits to the dripping candelabras, Raven’s Manor is disturbing in all the right ways. I won’t spoil the surprise, but definitely, definitely use the bathroom while you’re there. Drop in anytime to enjoy steaming concoctions and witch’s brews from the bar, or reserve ahead of time for the elixir experience, essentially a mixology class in a mad scientist murder basement. And if that doesn’t put you in the mood for romance, I don’t know what would.
21. Have bottomless mimosas on the Portland Spirit
Great for: Couples who love brunch.
Season: Any
Cruising on the Portland Spirit is my suggestion for the best date idea that they won’t see coming. You go downtown together and your date will be thinking, okay we’re going to coffee or the Saturday Market or something, but then you get on a boat instead. Once you cast off, you can take in the views from the deck or stay warm and dry at your table next to big windows looking out onto the Willamette River. Try a 2-hour daytime boat ride with a brunch buffet and mimosas. Or, go in the evening for a cruise with a three-course candlelit dinner.
22. Grab a bite at a food cart pod
Great for: Couples who have several non-overlapping food allergies.
Season: Best in summer or anytime it’s nice out.
One of the great things about Portland is that just about every neighborhood has a food cart pod. Besides being excellent places to find curry, falafel, and crepes stuffed with goat cheese and mushrooms (yep, I still remember them fondly), they can also be easy and laid-back destinations for a low-pressure first date. Don’t like the same food? No problem. Nothing to talk about? Do some people-watching and enjoy the sunshine. If lunch goes well, stroll around the neighborhood and do some window shopping. If it doesn’t, at least you got a burrito.
23. Get existential at Coffin Club
Great for: Couples with closets full of black.
Season: Any
Who are we? What does it all mean? Are we all just screaming into a cold and impersonal void to distract ourselves from the impending oblivion? These are some of the questions you won’t answer but may enjoy discussing over cocktails at the Coffin Club. This horror-themed bar gives a whole different meaning to the term mood lighting. Before pulling away the cobwebs to get to your booth, spend some time exploring to find all the skeletons, cages, skeletons in cages, and, of course, coffins at one of Portland’s most unusual nightlife spots. Look for events like live music and dance parties that happen downstairs. You’ll want to apply the eyeliner thick for this horrifically romantic night out.
24. Browse the shelves at Powell’s Books
Great for: Everyone
Season: Any
Whether you and your date are into murder mysteries, graphic novels, mushroom foraging guides, erotica, cookbooks, poetry, or cat training guides, Powell’s probably has what you’re looking for. As the world’s largest new and used bookstore, Powell’s contains over a million books and fills a city block. Multiple color-coded floors help you find your favorite genres, from popular fiction on the ground floor to the rare books collection at the top. After you shop, stop by the cafe for a coffee and a pastry. To keep the date going, you can head to the Living Room Theater across the street.
25. Go kayaking
Great for: Seeing if you and your date are in sync.
Season: Best in summer, both for the weather and manageable river currents.
For an active date in the summer with some beautiful scenery, it’s hard to beat kayaking. Take to the water on one of the rivers running through and around Portland in single or two-person kayaks. The Tualatin River and the Multnomah Channel near Sauvie Island are great beginner kayaking destinations near the city. I’ve also had a blast kayaking on the Willamette River, which is doable depending on the water level. Watch for bald eagles, admire the houseboats, and sync up your paddling with your date for a fun and romantic time on the river.
26. See immersive art at Hopscotch
Great for: A date that will expand your reality.
Season: Any
After months of meaning to go, I finally made it to Hopscotch. It did not disappoint. For one of Portland’s most unique nights out, wander through the exhibit spaces to see immersive art designed to engage the senses and transport you to another world. Stop by the bar on the way in to explore with a silly cocktail in hand. Hop on a trampoline with an interactive light show, decorate the walls with virtual spray paint, and create a dance video where you are your own backup dancers. Make sure to purchase tickets online in advance since they sell out frequently (one of the challenges I had making it there). Pro tip, evening times are better for dates than the daytime because the crowd is adults rather than families.
27. Oaks Park
Great for: Dates that get silly in all the right ways.
Season: All year for the roller rink and arcade. Spring through fall for the rides, mini golf, and games.
Although the rides at Oaks Park shut down for the winter, the roller rink is open all year. For date nights and nights out with your friends, the rink hosts Adult Skate and Gay Skate evenings from 7:30 - 9 PM. Find a schedule and special events at the roller rink here. If you and your date want to try out the rides, visit from spring through early fall. But first, a note of caution. I have never been motion-sick in a car, a boat, or anywhere on Earth other than on the ride with the spinning octopus arms at Oaks Park. Fortunately, I was not on a date at the time. The only thing worse than spending three hours wondering if you’re about to projectile vomit in an amusement park would be wondering if you’re about to projectile vomit onto your date in an amusement park. To play it safe, I recommend the bumper cars, the carousel, the roller coaster, skating, and the games. I can’t stress this enough. Not. The. Octopus.
28. Drink tea at the Chinese Garden
Great for: Enjoying a moment of tranquility together.
Season: Any
The Lan Su Chinese Garden is my vote for the classiest date in Portland, at least as soon as you step off the questionable sidewalks of Old Town and enter the secluded world behind the gates. To ease any doubts about its romantic potential, the name Lan Su means “garden of awakening orchids.” Based on the gardens of Ming Dynasty China, skilled artisans designed Lan Su’s buildings, walkways, art, and greenspaces to impart a sense of harmony and beauty. Although partly outside, covered walkways make it perfect for a rainy-day outing. As you explore the grounds, look for a reflecting pool, pavilions, calligraphy, sculptures, and poetry. Stop by the teahouse and head upstairs to hear the sound of rain on the roof while you enjoy your favorite tea and a plate of dumplings.
29. Play games at Ground Kontrol
Great for: Couples who were arcade high scorers growing up.
Season: Any
Ground Kontrol is both a bar and an arcade with two stories of classic video games and pinball machines. With games from the 1970s until today, it’s a place where you can find the familiar and nostalgic games of arcades past, plus still discover something new. After 5 PM, Ground Kontrol becomes a 21+ venue, which I think we can all agree is better date night vibes given the setting.
30. Go for a hike in Forest Park
Great for: When you and your person decide to do the Whole 30 together.
Season: Potentially any. Best when it’s not raining.
First, I want credit for making it through an entire list of suggestions on my hiking blog before suggesting a hike. Although last on the list, hiking in Forest Park is first in my heart for activities in Portland, whether alone, on a date, or with friends. Try out the Ridge Trail to see incredible views of the St John’s Bridge. Head to Lower Macleay Park and make the journey past the Witch’s House to Pittock Mansion. For couples who enjoy birdwatching, try out the trails around the Portland Audubon Center. Those who love botany might prefer the Hoyt Arboretum trails. For more options in the city, check out my article on hiking the parks of Portland.
If you’re interested in exploring outside of Portland, here are some of my suggestions:
In summary, these are my suggestions for the best fun and creative dates in Portland:
See the Portland Troll
Comedy in the Park
Explore the Kennedy School
Living Room Theaters
OMSI After Dark
Birdie Time
Portland Rose Garden
Cathedral Park
The Freakybuttrue Peculiarium and Museum
Rock climbing
Live music
Karaoke
Bar trivia
Wine tasting
Sunset at Council Crest
Have cocktails at a speakeasy
Japanese Garden
Portland Art Museum
Find the Collins Beach UFO
Raven’s Manor
Portland Spirit
Food carts
Coffin Club
Powell’s
Kayaking
Hopscotch
Oaks Park
Chinese Garden
Ground Kontrol
Forest Park
Enjoy your date!
With love,
Emma
More in Portland
Check out my partially overlapping list of the best indoor activities in Portland.
See all suggestions in and around Portland.
