8 Best Date Night Ideas in Portland

Are you a Portlandian who finds yourself without inspiring date ideas? Don’t worry—you’re in the right place.

We’ve rounded up some unique date ideas in Portland that go beyond the city’s big-hitters—because you want to impress your date with a range of fun activities that they might not know about. We’ve got ideas fit for all kinds of couples, from live-music lovers to strolling-the-street sweethearts.

All you have to do is take your pick. 

1. Tuck Into a Cozy Bar

For an intimate evening that makes you want to cozy up to your person, visit the best bars in Portland with romantic ambiances. Here are our top choices: 

• Les Caves & Le Clos: Find this speakeasy-esque wine bar by the black board in front of a wooden, alleyway door. It’s where wine cave meets intimate, outdoor oasis. You and your date only need to choose which setting fits your mood.
• Keys Lounge: A cocktail lounge in a living room setting, this place takes you back to the Mad Men era, with a wood-paneled bar, red leather booths, and soft lighting. Settle into one of the seating areas, and clink glasses to a budding romance.
• Scotch Lodge: If sipping manhattans or old fashioneds is more your thing, sidle up to the marble bar of this intimate spot.

2. Play Games at an Arcade

Want date ideas in Portland that are sure to make you feel like kids again? Have some fun (and get competitive) at an arcade or vintage game bar with your plus one. 

Retro Game Bar feels like your best friend’s basement in the 90s, so you’ll both feel right at home playing on game consoles from that era. Settle in for a game of Madden NFL ‘96 or Super Mario Brothers, with your video game-themed cocktails nearby.

If you both opt for the classics, plan a night at Ground Kontrol Classic Arcade and Bar, which has vintage video and arcade games. If you plan your date night right, you might even get to watch one of the monthly pinball tournaments.

3. See a Movie at Hollywood Theatre

Amp up your typical dinner-and-a-movie date with this rainy day date idea at Portland’s historic Hollywood Theatre. When the weather is bad, watch a good film and snack on a bucket of popcorn while sitting in this 1920s-era renovated theater. But you’re not limited to the classics here: Hollywood Theatre also shows new releases and lesser-known indie movies from decades past.

4. Hike in Forest Park

First-date etiquette doesn’t say that you need to sit across from each other at a restaurant. You can get out there and find adventure! 

As an outdoor-oriented state, date ideas in Oregon aren’t complete without mentioning all the incredible hiking opportunities Oregon has to offer. One of the largest city parks in the country is just waiting for you and your hiking partner to trek through its more than 80 miles of trails. 

Forest Park, just northwest of downtown Portland, boasts lush, green forests (hence, the name); beautiful streams; and well-maintained trails that make even the most amateur of hikers feel comfortable. Don’t miss Witch’s Castle on the Wildwood Trail for an eerie sight and a prime photo-op. 

5. Listen to Live Music

Pining for some good tunes? If you and your partner share a love for live music, this date idea in Portland is sure to hit the right note. From indie music venues to bars and restaurants with small, local acts, there are plenty of opportunities to check out live bands. 

A popular spot for indie music is Doug Fir Lounge, which feels like you’ve stepped into an intimate log cabin setting. Another cozy venue, perfect for couples on a date, is Wonder Ballroom, with wood-paneled walls and a small concert space. 

Another staple in the Portland live music scene is The 1905, whose tagline is “Food, Booze, Jazz.” Sounds like the makings of a perfect night out on the town with your love.

6. Opt for Old-School Luxury

Step back into the past, where dark, candle-lit spaces; burgundy leather booths; and white table cloths abound. Treat your partner to one of these date night in Portland restaurants that are sure to impress not only their taste buds but also their opinion of your date-planning expertise:

• RingSide Steakhouse: What looks like a simple building on the outside transforms into an inviting, dark-interiored steakhouse. Request one of the booths with its own lamp for the most intimate experience, and order a martini to round out your classic meal.
• Driftwood Room: Tucked into the Hotel deLuxe is this Art Deco, 1950s-era bar. While there’s no dress code for this spot, you and your date might want to put on your best fit to complete the glamorous experience.

After an evening at one of these sumptuous spots, we’re pretty sure you’ll get a second date.

7. Visit the Portland Saturday Market

In the city of all things arts and crafts, it only makes sense to plan a date at Portland’s open-air arts and crafts market. Open every Saturday, the Portland Saturday Market hosts tons of vendors selling handmade items and homemade treats. 

This is one of the best date ideas in Portland for a successful first date because you can both chat while doing an activity, which takes the pressure off of maintaining a constant flow of topics. Plus, when you find a unique treasure at one of the vendors, you’ll have a great first-date conversation starter. It’s a win-win.

8. Stroll Along SE Hawthorne Blvd

Sometimes, the best dates are those that don’t have reservations, that let you and your lover walk hand in hand with nowhere in particular to be. When you want a casual yet romantic date option, head to SE Hawthorne Blvd in the Hawthorne neighborhood. The stretch of this road between SE 30th Street and SE 50th Street hosts a great selection of vintage clothing stores, shops, cafes, and restaurants. It captures the heart of Portland.

First, grab a coffee at Common Grounds Coffeehouse, then pop into House of Vintage to try on some retro threads, meander through the small outpost of Powell’s Books, and check out the other neat shops nearby. Round out your day with a meal at one of the many eateries on this street and get a decadent chocolate bar to go from The Meadow.

When you’re ready to find your person, try Tawkify. Our matchmakers help you plan memorable dates that start out any new relationship on the right foot.