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SEE: Christmas Ships Parade
The Christmas Ships Parade began its 69th season Dec. 1, which you may have known if you were watching the event website’s countdown clock. The parade consists of about 60 boats ranging in length from 14 to 65 feet that hold brightly lit passengers such as the (inflatable) Grinch and a fishing Santa. Two fleets take to the Willamette and Columbia rivers almost nightly, and they’re free to watch (though you may prefer to take in the procession from the comfort of a waterfront restaurant). Willamette and Columbia rivers, christmasships.org. Times vary daily, through Dec. 17. No parade Dec. 7 and 11-12. Free.
GO: Ugly Sweater Party
It’s time to bust out that ugly Christmas sweater you only get to wear once a year and possibly win some fabulous prizes for doing it. Punch Bowl Social is encouraging everyone to don their most hideous themed knitwear—the more over the top the better if you want to be a contender in the costume contest. Downtown’s gaming palace will also serve special drinks with names like “Yule Shoot Your Eye Out” and “Not Ovaltine” in honor of the beloved holiday classic film A Christmas Story. Better yet, participants get one free hour of bowling, karaoke, darts or pingpong. Express your gratitude for the complimentary play by bringing a toy to Punch Bowl, which is a Toys for Tots collection site this year. Punch Bowl Social, 340 SW Morrison St., Suite 4305, 503-334-0360, eventbrite.com. 6:30-9:30 pm Wednesday, Dec. 6. Free.
GO: 13th Annual Tatas for Toys
If 20th century TV holiday variety shows were R-rated, they might have looked something like this. Tatas for Toys brings what are billed as the “finest North Pole dancers” to Dante’s for one night to raise money to purchase presents for OHSU Doernbecher Children’s Hospital (to date organizers have brought in more than $110,000 for the cause). The only person onstage likely to remain fully clothed is Santa—a great reason to show up to this event for the kids, but not for the kids. Dante’s, 350 W Burnside St., 866-777-8932, danteslive.com. 8 pm Thursday, Dec.7. $20-$150. 21+.
WATCH: Ludlow Ladd: The Poor Little Orphan Boy
If you enjoy stories about Christmas miracles, sad orphans and Victorian England, then you’ll want to buy a ticket to this Bridgetown Conservatory production. Ludlow Ladd: The Poor Little Orphan Boy is a holiday operetta that’s influenced by everything from Charles Dickens to Gilbert and Sullivan, though plenty of mock Christmas carols are thrown in to lighten the mood. Bridgetown Black Box at The Tiffany Center, 711 SW 14th Ave., 971-219-6452, bridgetownconservatory.org. 7:30 pm Thursday-Saturday, 2 pm Sunday, Dec. 7-17. $32.50.
LISTEN: Make the Yuletide Gay
Don we now our gay apparel and head to “the gayest holiday concert of all time!” This year’s holiday performance by the Portland Gay Men’s Chorus takes inspiration from both classic variety and modern sketch shows. Happily, yes, there will be plenty of innuendo and what the company describes as “suggestive themes.” Newmark Theatre, 1111 SW Broadway, 503-226-2588, pdxgmc.org. 8 pm Friday-Saturday, 3 pm Sunday, Dec. 8-10. $20-$56.
DRINK: Downtown Forest Grove Wine Walk
While everyone else tediously scrolls through websites for holiday gift ideas, you can make shopping fun again by doing it while buzzed. The Forest Grove/Cornelius Chamber of Commerce has paired 10 area winemakers with 10 downtown businesses for this event—attendees get a 1-ounce pour at each stop. By the time you’ve racked up eight or nine tastings, you should be in the mood to open your wallet. Both the boutiques and wineries will be eager to assist with any purchasing decisions, and you probably deserve a bottle of pinot to take home for yourself as a reward for all of that hard work. Check in at Forest Grove/Cornelius Chamber of Commerce, 2417 Pacific Ave., Forest Grove, 503-357-3006, fgcchamber.org/wine-walk-2023. Noon-5 pm Saturday, Dec. 9. $25 includes 10 1-ounce tastes and a logo wine glass.
GO: Portland SantaCon 2023
There are two types of people in this world: those who love SantaCon and those who despise it. If you’re in the latter camp, just plan to steer clear of downtown altogether this Saturday. However, if you love to dress like the big man, sexy Mrs. Claus, a reindeer, a Christmas tree or Banana Santa (we’ve seen you weirdos), get out that costume and join thousands of fellow drinkers who love to terrorize the city’s bar scene every holiday season. Keep in mind that this is not one of the free SantaCons—you’ll need to buy a ticket, but that waives all cover fees and comes with food and drink specials as well as entry in a costume contest with a $2,000 prize. It promises to be a night you won’t forget…or maybe you will. But that’s what the pictures are for. Starting point is Dixie Tavern, 32 NW 3rd Ave., eventbrite.com. 3 pm Saturday, Dec. 9. $14.99.
LISTEN: Gospel Christmas
The Northwest Community Gospel Choir’s mission is “to bring a message of faith, hope, love and joy through the perpetuation of gospel music as an original American art form.” After three remarkably difficult years defined by everything from a pandemic to high inflation, we could all use some of that faith, hope, love and joy—and it doesn’t get any more joyful than when this group of singers performs with the Oregon Symphony during the holidays. You can expect more than a dozen Christmas classics in the lineup—from “Joy to the World” to “O, Come All Ye Faithful” to “Go Tell It on the Mountain.” Arlene Schnitzer Concert Hall, 1037 SW Broadway, 503-228-1353, orsymphony.org. 7:30 pm Saturday and 4 pm Sunday, Dec. 9-10. $25-$117.
GO: Rose Quarter Guitar Show
Guitar players at every skill level should be stoked about this gathering of stringed instruments. The Rose Quarter Guitar Show will have new and used Fenders, Gibsons, Voxes and more for attendees to buy, trade or simply gawk at. Organizers encourage you to get there early since they’ll be giving away 100 sets of C.F. Martin acoustic strings and 100 sets of Darco Electric strings at the door. Guitars won’t be the only equipment available to purchase—vendors will also have amps, effect pedals, lap steels, banjos and even ukuleles. Veterans Memorial Coliseum, 300 N Ramsay Way, 503-235-8771, westcoastguitarshows.com. 10 am-3:30 pm Sunday, Dec. 10. $15 at the door.
LISTEN: Powell’s Books Presents Henry Winkler
You may know him as the cool guy in the leather jacket from Happy Days or as a Los Angeles acting teacher caught up in a murder investigation in HBO’s Barry, but you won’t really know Henry Winkler until you hear more about his life from the man himself. The Emmy-winning actor has just released a memoir titled Being Henry, and at this live appearance he’ll be describing some of the content in his book, which includes everything from the struggles of dealing with severe dyslexia, the initial troubles of having a career defined by The Fonz, and how therapy played a key role in his personal and professional development. We can only hope he will also talk about that pop culture-defining moment when Arthur Fonzarelli literally jumped the shark. Revolution Hall, 1300 SE Stark St., 971-808-5094, revolutionhall.com. 7:30 pm Tuesday, Dec. 12. $40.