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14 lovely things to do for Valentine’s Day in Sherwood

Enjoy Galentine’s, wine pairings, live theater, crab dinner, cookie decorating, and more

14 lovely things to do for Valentine’s Day in Sherwood
Stay local and celebrate love in Sherwood this season. (Jules Rogers/Sherwood Sun)

Valentine’s Day is a time for romance, connection, and a little sparkle — where will you fall in love this season?

We’ve pulled together some local, family-friendly dates for Galentine’s and Valentine’s, whether you want to celebrate with your love or with your gal pals.

Here’s what’s on our calendar in February, for date ideas from chocolate and wine pairings to live theater, and dice game fundraisers to pajama parties — and don’t forget the crab dinner, romance movie trivia, and cookie decorating class.

Remember to add your events to the Sherwood Sun Calendar by emailing the editor or sending us a tip — it’s free advertising that supports your event and helps get the word out to your neighbors who care right here in town!

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Galentine’s Bunco Fundraiser: Roll with your Gals

Sunday, February 1, 5-8 p.m.

BearKat Brewing Co., 20345 S.W. Pacific Hwy. Ste. 404

Play dice and support the Sherwood High School Grad Night 2027 for a safe, substance-free graduation celebration. This event includes a raffle ticket, bunco prizes, food, drinks, and photo booth. Tickets cost $30 per person. 

Speed Date & Mingle (45+)

Monday, February 2, 6:30-8 p.m.

503 Uncorked, 22578 S.W. Washington St.

Event Link

Meet and mix with new people at this speed dating event by Epiphany Match. Have conversations and find someone special who shares your passions. This event is open to singles aged 45 and up. Entry costs $10 at the door.  

Galentine’s Day Pajama Party

Friday, February 13, 5:30-8 p.m.

Sherwood Bookstore, 16771 S.W. 12th St. D

Event link

The Sherwood Bookstore is hosting a Galentine’s Day Pajama Party, an extra-special night at the bookstore. This event is open to gals, pals, theys, and thems ages 16 and over, featuring finger food and snacks, wine poured by Adelsheim Vineyard, and facials and other services by Sherwood Aesthetic Medicine. There will also be book giveaways and other prizes. Tickets are $25. 

Paint & Sip

Friday, February 13, 6:30-8:30 p.m.

Langer's Entertainment Center, 21650 S.W. Langer Farms Pkwy.

Event link

Enjoy a guided painting session for beginners or seasoned artists, aged 14 and up. Paint a serene garden scene with a spray of flowers.

Valentine’s Wine & Chocolate Pairing

Saturday, February 14, noon-5 p.m.

Blakeslee Vineyard Estate, 20875 S.W. Chapman Rd.

Celebrate with a variety of luscious wine and chocolate pairings, including exclusive library selections and flavors, along with live music by Lew Jones. This event is complementary to wine club members plus two guests, and $30 for non-members, waived with a minimum purchase. 

American Legion Crab Feed & Sweethearts Dinner

Saturday, February 14, 4 p.m., 6 p.m.

American Legion Post 56, 22548 S.W. Pine St.

American Legion Post 56 is hosting its annual crab feed with two seating times. Fresh, live Oregon Coast Dungeness crab is cooked in the morning and served in the afternoon, or guests can opt to have a chicken dinner instead. Dinner is served with coleslaw, corn on the cob, garlic bread, and cookies. Tickets cost $30 for a whole crab dinner or $15 for a half chicken dinner, and sales close February 10.

Valentine's Day Party

Saturday, February 14, 5-9 p.m.

Generations Bar & Grill, 15982 S.W. Tualatin-Sherwood Rd.

Event Link

Join in a romantic night at Sherwood's family-oned sports bar Generations Bar & Grill for an exclusive menu, complementary bubbles, and live music by Mister Mike Vaughn from 7-9 p.m.

Saturday, February 14, 12:30 p.m.

BearKat Brewing, 20345 S.W. Pacific Hwy.

Event Link

Join in a red, white and pink cookie decorating class for all ages, featuring Baked in Sherwood, perfect as a gift for a special someone — or to enjoy right away yourself. Tickets cost $50, and include supplies and a beverage.

Huckle Buck Highway live music at Sherwood Elks Lodge

Saturday, February 14, 7 p.m.

Sherwood Robinhood Elks Lodge #2342, 22770 S.W. Elwert Rd.

Event link

Elks members and their guests are welcome to join the Freshman show of Huckle Buck Highway, a Silverton-based country and classic rock band.

Second Saturday Work Party

Saturday, February 14, 9:30 a.m.-noon

Tualatin River National Wildlife Refuge, 19255 S.W. Pacific Hwy.

Event link

Join in for a Valentine's Day planting celebration on property normally closed to the public. All ages are welcome, and tools, glove, and refreshments will be provided. RSVP required.

Romance Movies Trivia

Sunday, February 15, 11:30 a.m.-1:30 p.m.

The Tack Room at Langer's, 21650 S.W. Langer Farms Pkwy.

Event link

Test your knowledge with free trivia on romantic cinema at a brunch buffet with $2 mimosas and $150 up for grabs in prizes. This event is for those ages 21 and up.

King Lear by the STARS 

February 6-15, showtimes vary

The Robins Nest Theater, STAR Society, 22520 S.W. Washington St.

Event link

The Sherwood Theater and Arts Resource Society is performing Shakespeare’s King Lear in live performances through Valentine’s week. Performances are offered at 3 p.m. and 7 p.m., depending on the day, and tickets cost $15-20. 

The Importance of Being Earnest

February 12-13, showtimes vary

The Bowmen Theater, Sherwood High School, 18800 S.W. Haide Rd. 

Event link

Join the audience for Sherwood High School’s winter play, the classic Oscar Wilde comedy about love and lies. Tickets are available online or at the door. 

Movies with the STARS: The Way We Were

Saturday, February 21, 7:30-9:30 p.m.

The Robins Nest Theater, STAR Society, 22520 S.W. Washington St.

Event link

The Robin’s Nest Theater turns into a movie theater for microcinema night with this romantic drama from 1973. Tickets are $10.

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