Great Date Ideas in Portland, Oregon

Portland is known for its roses
Portland is known for its roses | © David L. Moore - OR / Alamy Stock Photo
Photo of Elena Alston
24 July 2020

In the Oregonian woods that flank Portland, there are great green groves of trees. Firs, redwoods and western junipers grow in the Pacific Northwest. Further in the background there’s the preening heights of Mount Hood, a sleepy volcano with a snow-dusted peak. In short: Portland is a romantic city. And not just because of its surroundings. It’s a great place for a date. But if you’re stumped for a venue, fret not – and read on. Here’s what our local insiders suggest.

McMenamins Edgefield

Boutique Hotel

The historic Edgefield hotel was erected in 1911 as a remote county farmstead. It’s now a luxuriant destination resort, seeded in the Oregonian wilderness, but located just 20 minutes by car from the dead center of downtown Portland (depending on traffic). It’s a Luddite’s dream getaway – there are no phones or TVs in any of the 100 guest rooms in the main house, which are furnished with tasteful, turn-of-the-century decor. But it’s also worth the trip without an overnight: you can walk its rambling, rose-studded gardens with a pint in hand, or see some glass being blown. It’s a scenic backdrop for wooing. Recommended by local insider Madeline Churm

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International Rose Test Garden

Botanical Garden
Map View

Dubbed the City of Roses, Portland takes great pride in its International Rose Test Garden, with over 10,000 rose bushes and more than 650 varieties that bloom in full force during the summer months. The garden is made up of three sections: the Royal Rosarian Garden, the Shakespeare Garden and the Miniature Rose Garden. When the sun heats the garden, wonderful scents ooze out, making it an aromatic haven – and romantic by nature. Recommended by local insider Madeline Churm

OMSI After Dark

Map View

If you’re looking for a night out with an intellectual bend – but one that encourages a fair bit of carousing – then this might be the right date night for you. These 21 and older events invite visitors into the Oregon Museum of Science and Industry (OMSI) after hours. There are drinks and dancing, sprinkled with a little bit of science. OMSI is located smack in the middle of town, so it’s easy to head there after dinner for some tipsy exploration of attractive insect displays. Recommended by local insider Jordan Singh

Hey Love

Bar, Cocktails
Map View

This spot wears a lot of hats. It’s self-described as a “community meeting hall, an afternoon study spot, an exceptional cocktail lounge, a hidden garden and a house party, all in one.” All that aside, for a date, your best bet is to head in around 9pm, when the fruity cocktails start flowing. The vibe here is warm – and not merely because the bar is festooned with all manner of tropical flourishes. At any time of day, Hey Love has got a homey, inviting atmosphere. So it’s a great place to get to know someone in a comfy space. This hip joint is also affiliated with the Douglas Fir Lounge, a music venue located just a block away. So keep an eye out for joint events run by both – and you can cover dinner, drinks and a show in just a few steps. Recommended by local insider Jordan Singh


Bar, Cocktails
Map View

For a date night that scores points for originality, head to DIY Bar. In addition to booze, you can quench your thirst for artistic expression – by making arts and crafts. This watering hole is also a workshop, and you can choose from a menu of many crafty endeavors – from making macrame to dunking T-shirts into tie-dye – depending on the craft kit you purchase. It’s a plum locale for a couple, or a group of friends. Plus, if it all goes bottoms up, at least you’ll get a cool, beaded bracelet out of it. Recommended by local insider Jordan Singh

Hollywood Theatre

Movie Theater
Map View

The Hollywood Theatre is a storied building, which opened its doors in 1926 to host vaudeville shows and run silent movies, and looks very much the same as it did nearly a century ago. Today, it offers an offbeat setting for indie flicks and obscure cinema, as well as classic films and community talks. In 2015, movie buffs brought 70mm projection back to the Hollywood – so you can enjoy old reels of movies such as My Fair Lady (1964) and Lawrence of Arabia (1962), or recent flicks that ditched digital for reels of film, such as Dunkirk (2017) and The Hateful Eight (2015). Some people, including director Quentin Tarantino, insist 70mm has better resolution than streaming in 4K. In any case, this throwback theater has a lot to offer for serious film buffs and oblivious popcorn munchers alike. Recommended by local insider Madeline Churm

These recommendations were updated on July 24, 2020 to keep your travel plans fresh.

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