Looking for fun date ideas this Valentine’s Day? Below is a list of 14 events around Oregon held this Valentine’s Day weekend.

Love Letters

Stumptown Stages presents the Pulitzer Prize-nominated play Love Letters by A.R. Gurney, starring Jack Bannon and Ellen Travolta. This story is told through the reading of letters that demonstrate lifelong friendship and romance.

Thursday, Feb. 12 to Saturday, Feb. 14; Brunish Theatre; $25-35

Smokey Robinson Live

Smokey Robinson performs with the Oregon Symphony at the Arlene Schnitzer Concert Hall for his “Smokey and Friends” tour.

Saturday, Feb. 14; 7:30 p.m.; Arlene Schnitzer Hall; $25-137

Portland Spirit

The Portland Spirit offers two days of Valentine’s Day cruises, including a four course dinner and entertainment from The Bylines.

Friday, Feb. 13 & Saturday, Feb. 14; 7:00-9:30 p.m.; The Portland Spirit; $99 per person

Romance on the Rails

Mt. Hood Railroad provides a scenic ride and four-course meal for Romance on the Rails special.

Saturday, Feb. 14; 4:30-8:30 p.m.; Mt. Hood Railroad; $85 per person

Sausage Fest

Mt. Angel Wurstfest offer their seventh annual sausage fest complete with beer, live German music, and sausage from Mt. Angel Sausage Co.

Friday, Feb. 13 & Saturday, Feb. 14; 10:00 a.m.-10:00 p.m.; Mt. Angel Festhalle; $5-10

Dance for Romance

The Bossanova Ballroom hosts live music, a poetry slam, belly dancing, burlesque, and acrobatics for singles or couples—no experience necessary.

Saturday, Feb. 14; 6:00 p.m.-3:00 a.m.; The Bossanova Ballroom; $10-160

Mardi Gras Ball

Celebrate Valentine’s Day, New Orleans carnival-style at Portland’s Mardi Gras Ball.

Saturday, Feb. 14; 7:30; Wonder Ballroom; $25-41

Romance in the Cellar

The Eola Wine Cellars in Rickreall, Ore. hosts Romance in the Cellar, a dinner complete with a full wine selection.

Saturday, Feb. 14; Eola Hills Wine Cellars; $99

Cabaret Cupid

Hillsboro’s Bag & Baggage Productions hosts their annual showing of “Cabaret Cupid” featuring David Saffert.

Saturday, Feb. 14; 7:30 p.m.; The Venetian Theatre; $30-50

Classic Country Duets

Some of Portland’s best country musicians perform classic country duets by Gram Parsons and Emmylou Harris, Johnny Cash and June Carter, Dolly Parton and Porter Wagoner, and many more.

Saturday, Feb. 14; 9:00 p.m.; The Secret Society; $10-12

Festival of Dark Arts

Fort George Brewery features over 60 brews of dark beer on tap at the Astoria Brewery.

Saturday, Feb. 14; 12:00 p.m.-10:00 p.m.; Fort George Brewery; $10-30

Doll and Teddy Bear Show

Crossroads Doll and Teddy Bear Show features collections of collectible antiques including dolls, bears, miniatures, and books.

Saturday, Feb. 14; 10:00 a.m.-4:00 p.m.; Kleiver National Guard Armory; $4-8

My Muddy Valentine

The city of Tualatin hosts “My Muddy Valentine” 5k obstacle run, providing food, drinks, music, and even warm showers.

Saturday, Feb. 14 & Sunday, Feb. 15; Lee Farms; $70

Wine & Chocolate Weekend

Over 20 wineries in the Columbia Gorge host chocolate & wine tastings and giveaways

Saturday, Feb. 14-Monday Feb. 16; Columbia Gorge Wineries in Washington and Oregon


Hana is currently pursuing an undergraduate English degree with a Spanish minor at Concordia University Portland. She loves creative writing and reading children's books and someday hopes to publish her own. Favorite hobbies include cooking, cleaning, eating ice cream, and singing Disney princess songs.