Portland plus one: fun date ideas

Portland, Oregon

Surrounded by lush countryside and a bustling downtown, Portland brims with a wide variety of romantic places to bring a date. Whether you’re strolling down a scenic hike or enjoying live music and a candlelit dinner, you and your potential S.O. won’t be able to resist falling in love with the city—and possibly each other.

Horsetail Falls in Columbia River Gorge, Greater Portland Region.
Horsetail Falls in Columbia River Gorge, Greater Portland Region.

Dine by Candlelight
Downtown Portland boasts some of the city’s best eateries. Dine in class and head to El Gaucho on Southwest Broadway for a romantic, candlelit dinner. Located in the historic Benson Hotel, the restaurant prides itself in offering a fine-dining experience reminiscent of a bygone era. Share the Chateaubriand—center-cut tenderloin for two carved tableside. For dessert, be sure to order the flambéed bananas foster and cherries jubilee, also prepared right at your table. You can enjoy live flamenco guitar music seven days a week at El Gaucho.

Take a Stroll
Portland is surrounded by some of the most beautiful countryside in the Northwest, with plenty of options for a scenic hike. Columbia River Gorge National Scenic Area is just 20 minutes away, with dozens of trails that wind through shady woods, creeks and waterfalls. For a more tranquil stroll, steer clear of the frequently visited Multnomah Falls in favor of the lesser-known Horsetail Falls, where the path passes right behind the 176-foot waterfall. The Horseshoe Falls Trail is short and not too strenuous, with connections to several longer routes.

Get Lost in Books
If you and your date love getting your hands on a good book, head to Powell’s City of Books, located in the heart of downtown. As the largest new and used bookstore in the world, Powell’s spans an entire city block on West Burnside Street, housing more than 1 million books and over 3,500 different sections. Check out the cozy Rare Book Room, where you’ll find a treasury of autographed first editions and collectible volumes.

Catch a Concert
A renovated church now owned and operated by musicians, Mississippi Studios hosts over 500 shows a year with local, national and international musicians in every imaginable genre. With a capacity just under 300, it’s an intimate space with plenty of sitting and standing room on the floor, plus balconies on three sides. For food and drink, head next door to Bar Bar, where you and your date can bond over burgers, toasted raviolis and craft cocktails. Try the Hottie McTippy—a house toddy made with bourbon, ginger-honey syrup and hints of cayenne—or The Secretariat—vodka with pear puree, lemon and vanilla simple syrup.

Head to the Theater
Many theaters in Portland have added libations to the equation, creating a new type of establishment called a “brew ‘n’ view.” North Ivanhoe Street’s St. Johns Theater and Pub is one of the best. Housed in a domed building built in 1905 for the World’s Fair and only intended to stand for six months, the theater shows new releases and second-run movies while boasting charming, Victorian-palace-meets-wild-west-saloon vibes. The attached pub serves tasty burgers and an ever-changing craft beer selection. Up the spice factor during your date and try the Philadelphia Collins burger with bacon, smoked mozzarella, roasted peppers and habanero mayo.