Portland schools open their doors to welcome kids back on August 27, which means the lazy summer days are almost done. Sneaking off for a romantic night out with your partner can be downright difficult once early morning alarms and coveted family time on the weekend kicks back in. Get one last date night in while the gettin’s still good! Grab a drink, dine out or sneak away for a whole night. Scroll down and check out a list of the best date night ideas we’ve put together for you.

photo: courtesy of The Benson Hotel

Escape Overnight

The Benson Hotel
If you are in desperate need of a dash of class with a whole lot of romance, The Benson Hotel in downtown Portland has it all. Recently renovated, the accommodations feature a swanky lobby, stunning multi-level chandelier, and rooms with well-appointed furnishings and luscious bedding.

The Palm Court, Benson’s restaurant, is also featuring a new menu that includes incredible offerings like Chicken Al Matone served with asparagus, lemon and rosemary; braised Short Rib Hash served with two eggs and sweet chili aioli; line caught Albacore served with avocado, cucumber and jalapeño; and avocado toast served with radish, saba, ricotta salata and a poached egg.

The restaurant and hotel upscale your experience withlive jazz entertainment by local musicians every Wednesday and Thursday from 8:30-10 p.m., and Friday and Saturday from 8:30-11:30 p.m..


309 SW Broadway
online: coasthotels.com/hotels/oregon/portland/the-benson-hotel/

Kennedy School
A classic McMenamin’s establishment, the campus is a historic elementary school-turned-hotel. With multiple bars to choose from and a cozy theaters, this is a perfect dinner and movie option, but the fun doesn’t have to stop there. The beautiful and private outdoor soaking pool is a perfect romantic setting for after the show ends. Bring your drink from any of the small bars around the school—just ask for a plastic cup when you order! 

The Kennedy School is also a hotel with rustic rooms that help you unplug from the world and focus on one and other. Book ahead of time and enjoy a mini staycation.

Soaking is $5/hour/per person, bring your own towel
Soaking pool is open until 8 p.m. for general public.

5736 NE 33rd Ave
Online: mcmenamins.com

Doug Fir Lounge
If movies aren’t your thing, catch some of the best music that comes through town at this world-renowned music venue featuring a futuristic log cabin vibe. Join them in celebrating 13 years of great music by making a whole night of it—dinner, drinks, a show, and  an overnight stay at ultra-cool Jupiter Hotel next door. The food is local, comfy, served in a dining room with an echo of Twin Peaks. And the music downstairs offers a show almost every night of the week, an eclectic mix of tunes sure to please.

830 E Burnside St 
Online: dougfirlounge.com

photo: heather via yelp

Drinks on the Town

Spanish Coffee at Huber’s
Ask any Portlander for suggestions on top spots to go on a date and this locale is likely to come up. Grab a Spanish coffee, the drink they might be best known for as they claim to have invented—though in reality the drink was probably “borrowed” from other bars. Reguardless, they make sure you get more that a coffee with a kick when they ignite rum and triple sec in a sugar-rimmed class that is  then covered in Kahlua, coffee, and topped with fresh whipped cream. 

411 SW 3rd Ave.
Online: hubers.com

The Sapphire Hotel
This sexy little cocktail lounge is located right on the historic Hawthorne Ave. in the SE. Dimly lit with comfortable and plush seating, the atmosphere is designed for sipping and kissing. Try The Most Popular Drink, made with Vodka, lime, coconut, orgeat, Shirley Temple Soda and Pop Rocks. Or sip on the Point of No Return: the perfect mix of bourbon, rye syrup, Amaro Cio Ciaro and tiki bitters. Whichever drink you choose, you are sure to end the night with that spark relit and burning bright.

50008SE Hawthorne Blvd
Online: thesapphirehotel.com

photo: Hubers

Dinner and a Show

Hollywood Theater
Head to Hollywood Theater for a change of pace from the regular movie routine. Not only do they show the usual new releases, they have a rotating selection of Signature Film Series that add up tp serious fun, like Kung Fu Theater or Queer Horror. Join in on the fun with their B- Movie Bingo (just what it sounds like) or test your knowledge with their monthly Movie Quiz. With local beer flowing, pizza, and the usual concessions, it’s a movie date night to remember!

4122 NE Sandy Blvd
Portland, OR
Online: hollywoodtheatre.org

Dinner and a Show at the Schintz
Go classy with a show at Portland’s renowned theater. Start out the night down the street at Higgins, offering classic Pacific Northwest local and sustainable fare, expertly paired with beer and wine. Then head to your seats at the Schnitzer for a show. Upcoming options include symphonies like Pirates of the Caribbean or Stravinsky, and comedians like Lewis Black or Adam Sandler.

Higgins Restaurant
1239 SW Broadway
Online: higginsportland.com

Arlene Schnitzer Concert Hall
1037 SW Broadway
Online: portland5.com

photo: stumptown dance via yelp

For Fun

OMSI After Dark
It’s Night at the Museum for the 21 and over crowd, filled with drinks, water rockets, experiments, and fun! This monthly event offers a themed night out at Portland’s favorite science museum, open late from 6-10 p.m. Food vendors, drinks, science demonstrations, and even performances all center around a theme like the upcoming Good Vibrations, Brewfest, Spirits, and Mysteries of Egypt. It’s a popular event, so grab tickets online before you go!

1945 SE Water Ave
Online: omsi.edu

Ground Kontrol Arcade
Go back to your childhood with Ground Kontrol’s classic arcade games! Leave the kids at home and head to this downtown hot spot, which becomes a kid-free, bar-open zone at 5pm each night. For a quarter per play, you can try your hand at over 60 arcade games and 27 pinball machines. Add a live DJ and a full-service bar and it’s a date night chock full of fun. They also have regular events like comedy shows, trivia nights and game tournaments.

115 NW 5th Ave.
Portland OR
Online: groundkontrol.com

Get Your Dance On
Oregon’s largest weekly swing dance is a rolicking good time! Beginners are more than welcome to this social dance, which pulls partners together in a happy jazzy beat. Come early for the weekly beginner lessons, then dance your socks off the rest of the night. Many people return for more lessons: it’s a fun, affordable way to learn and try out your moves. And when you master the beginning steps, you can move on to the rotating Intermediate lessons, teaching tricky turns and special moves from the Charleston!

$10 cover
Norse Hall 111 NE 11th
Portland, OR
Online: stumptowndance.com

—Annette Benedetti


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