We are all about parent-kid dates, but this post isn’t all about that. This is for that magical, elusive, nobody’s sick, sitter’s secured, go out on the town with your person date — summer edition. We’ve got ideas to take full advantage of the season, from free to splurge-worthy. Happy date night!
Free Summer Dates, Because Sitters are Expensive
Comedy in the Park
Every Friday, all summer long you can attend a free Kickstand Comedy show in Laurelhurst Park. This event is popular, so arrive early.
Check out our reel of a recent comedy show!
Parks & Recreation Free Outdoor Concerts, Movies, and Events
Portland Parks & Rec hosts free summer concerts, outdoor movies and cultural events throughout the summer at parks across town. Looking for Cuban music, Zimbabwean marimba, Brazilian samba? They’ve got it all. Want to watch Wicked on the big screen under the stars? It’s on the calendar. Check out their full summer schedule of events here.
The Classic Picnic
There’s nothing more romantic and low-cost than the classic picnic. And if you’re looking for inspo for that perfect spot, lots of these hikes offer scenic vistas.
Shakespeare in the Park
Original Practice Shakespeare travels to parks across Portland to speak the speeches, trippingly on the tongue. Check out their schedule here. All shows are free!
First Thursdays in the Pearl
From April to October, there’s a monthly street gallery featuring original work on NW 13th street between Hoyt and Kearney, packed with artists, musicians and art-lovers. It’s free to attend, though you’ll definitely be tempted to take home a piece or two.
The Shack at Sellwood Park
Plan a free date at The Shack at Sellwood Park, where you can take a BodyVox dance class together beneath the trees or pack a picnic for Friday night’s free live music. Settle onto a blanket under the park’s 100-year-old firs, listen to local musicians and enjoy one of the sweetest summer evenings in Sellwood.
Festival Fun
Portland is serious about festivals; there’s at least one (usually more) every weekend, all summer long. Most are free to attend!
Bike Summer
Grab your bikes and join one of the hundreds of free, volunteer-led rides offered during Bike Summer, also known as Pedalpalooza. The festival runs throughout June, July and August, with rides ranging from relaxed neighborhood cruises to delightfully specific themed adventures. Most are free, open to the public and extremely Portland. Pick one that sounds fun, add lights to your bikes and make a date of exploring the city on two wheels.
Sunset at Mocks Crest
For sunset and people watching, there’s no place quite like Mocks Crest on the Skidmore Bluffs. From the Bluffs, you can catch views of the Willamette, the West Hills, the rail yard and the city skyline. But the real fun is what you might see in the park — unicycles (probably), hula hoops (almost definitely), a wedding on stilts (it’s been rumored to have happened). It’s a great spot to feel reconnected to Portlandia.
Splurge-Worthy and Slightly-Splurgy Date Nights
Farm to Plate Experiences and Live Music Nights at Topaz Farm
You’ve probably already visited Topaz Farm with your kids on one of their free Animal Talks, but Topaz also hosts some incredible events perfect for date night. At their Farm to Plate dinners, you’ll eat a five-course meal under a 500-year-old oak tree, prepared by “culinary power couple” Christian and Janelle Ephrem. The dinners are made from ingredients grown on the farm — some harvested the very day they serve them to you. Or check out their Live Music Nights: the music is incredible, and you can sip craft beer or wine and eat a picnic dinner while you listen.
Conspirators Coffee Lounge
If you want to have a spooky good time, and eat the best frozen custard of your life, there’s only one place to go for date night: Conspirators Coffee Lounge. This Old Town establishment is a speakeasy-style coffee shop, that requires a password to enter through Black Cat Frozen Custard (you’ll find the latest one on their social accounts). Don’t miss ordering the custard. You won’t regret it.
Check out our reel here!
Summer Sports Dates
Take yourself out to a game! Catch the collegiate Portland Pickles in Lents for hot dogs, delightfully weird theme nights and the antics of Dillon, the team’s giant pickle mascot. Or head west to see the Hillsboro Hops play in their brand-new ballpark. Looking for something besides baseball? Cheer on the Portland Fire during their debut WNBA season, or catch a summer soccer match with the men’s Portland Bangers FC or women’s Portland Cherry Bombs FC at Lents Park.
Urban Wine Tasting
It’s a pretty short drive to wine country — but did you know you don’t actually need to leave Portland to have a true wine tasting experience? With over a dozen in town, you’ll have plenty of opportunities to get those palates working. Here’s a list of the wineries.
ZooNights
Experience the Oregon Zoo after hours during ZooNights, happening Friday evenings from June 19 through August 21. Wander the zoo’s forested grounds, spread out a blanket for live music, grab dinner from the food carts and stop for evening keeper chats and animal activities. Local beer and wine are available for adults, making this an easy summer date night that still feels like an occasion.
Get into the Spirit(s)
Portland’s distillery row is the place to go for tasting locally-made spirits. Build your own tasting-room crawl through Portland’s craft distilleries, sampling locally made whiskey, vodka, gin, rum, brandy, amaro, and more. Check out where to go here.
OMSI After Dark
When you’ve got a kid-free evening, OMSI might not be the first place you think of. But hear us out. OMSI After Dark is just for adults. That means you may actually have a chance to look at the exhibits. Plus every month, they have a theme — like astronomy, or even beer or spirits. They have vendors, artisans, science experiments and presentations around that theme, and they serve alcohol.
Sunflower Fields
For the perfect August date night, check out one of the many sunflower fields in the Portland metro area. Entry is usually affordable, and strolling through the flowers basically shouts romance.
Looking for more date night inspo? Check out these budget-friendly ideas!