Sometimes you just want to hang out with your gal pals, sip a beverage of your choice and share a fun activity together. Wine & Paint nights are popping up all over town. It doesn’t matter if you can’t paint, that’s not the point. It’s a monthly event at the Winery at Manzanita in Bend. You don’t even need to come up with a subject. The theme in February is “red lanterns” in honor of Chinese New Year and in March it’s “lucky rainbow meadow.” A $55 fee includes all the art supplies. No experience necessary. If those don’t inspire you, a Paint Your Pet class is also scheduled in March. There’s also a paint and sip event at Craft Kitchen & Brewery on March 19 where painters will create a scenic poppy field.
Those paint sessions are hosted by Sarah Swoffer of Let’s Paint. The scenes she selects involve community input. “Every four months I send a ballot out to our art community, and everyone votes on the paintings for the next quarter,” she tells the Source. For the pet classes, Swoffer does a lot of prep work, sketching the animals on each canvas in advance of the paint sessions.
“The majority of classes are step-by-step. I do a step and explain it, then they do a step and I walk around and help them. We don’t try to copy. Painting should be relaxing and creative,” Swoffer explains. She began offering art classes to children in her backyard years ago when everything went online, but she eventually realized adults needed an outlet as well.
“Art is very therapeutic and a wonderful activity to tap into your curiosity, build confidence and connect with others,” she says. Swoffer’s name may be familiar to some of you. She won “Best of the Nest Arts Instruction” for the past three years.
A paint and sip afternoon is scheduled on Valentine’s Day at Austin Mercantile in SW Bend. The afternoon event is led by Kristen Buwalda of Chalked Creative. The fee includes a canvas, art supplies, a guided tutorial and one beverage. Children are welcome. Buwalda began doing paint & sip classes in 2017 when she worked at Crater Lake Spirits.
“I teach in a “direct to draw” method where people literally follow me step by step,” Buwalda says. “I make sure all of my guests know that I am there to support and guide them, and that we are in it together… Art shouldn’t be serious!” Her subjects are generally landscapes or nature related. Buwalda is at Austin Mercantile once a month, at Flights usually every other month and occasionally at Bevel Craft Brewing and Bend Cider Co.
“I also have an event on the 13th at Flights Wine Bar! This is the fourth year I’ve done a “Galentine’s” event at Flights!” Buwalda says.
It’s Just Paint offers paint and sip parties in the Redmond area. On Wednesday, Feb. 11 the theme involves painting your partner with a twist. The fun is led by Sarah Van Loan who plays music and does her darndest to make you laugh. “I have a great playlist of music. I do a bit of stand-up comedy. We always have a cocktail at arm’s length and with step-by-step instructions and a sense of fearlessness, we conquer the canvas!” she says. “The painting we will be doing is a buck and a doe that are on two separate canvases connected with the antler crossing the top. A heart is hanging from the antler.” All ages are welcome. Elements With Design will also be there with their Permanent Jewelry Pop Up shop.
OK, so you’re not the creative type. What about Sip & Shop with your besties? An artisan market is scheduled on Monday, Feb. 2 at the Winery at Manzanita from 2-7pm to celebrate an early Galentine’s Day (an unofficial tradition ahead of Valentine’s Day celebrating friendships).
Paint & Sip
Wed. Feb 11 6pm
Wild Ride Brewing
332 SW 5th St, Redmond
facebook.com/events/1415923063536692
$38
Wed. Feb 18 & March 11 6pm
The winery at manzanita
550 SW Industrial Way #194, Bend
bendwinebar.com/events
$55
Fri, Feb 13 6pm
1444 NW College Way, Bend
opentable.com/r/flights-wine-bar-and-restaurant-bend?ref=1068
$50
Sat, Feb 14 2pm
Austin Mercantile
19570 Amber Meadow Dr #190, Bend
chalkedcreative.com/events
$48
Galentine’s Sip & Shop
Mon, Feb 2 2-7pm
the winery at manzanita
550 SW Industrial Way #194, Bend
bendwinebar.com/events
Free
This article appears in the Source January 29, 2026 and Toast! 2026.
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