Welcome to Eastside Insider, your backstage pass to the best holiday happenings this week! There’s a lot to cover this time of year, I couldn’t fit it all in! What we lack in live music, we’re making up for in events. What if I post all the stuff that didn’t make it in the newsletter into Instagram? 🤔 Reply to [email protected] and let me know what you think.

Let’s get to it!

Live Music 🎸🎷

Thursday

Rouge Cocktail Lounge - Zach Lombardo 7:30pm
Willows Lodge - The W Lovers 6pm
Village Wines - Jaeden Luke 7pm
Vino Bella - Nick Mardon 5:30pm

Friday

The Grape Choice - One on One 5pm
Willows Lodge - Caety 6pm
Northwest Spirits - Rocci Medawar 5pm
Patterson Cellars, Hollywood Hill - Norman Baker 6pm
Vino Bella - The Nick Mardon Trio 7:30pm

Saturday

Northwest Cellars - Jarrett Renshaw 5pm
The Grape Choice - New Age Flamenco 5pm
Willows Lodge - Jessie Lorenz 6pm
Patterson Cellars, Hollywood Hill - Jim Basnight 6pm
Chandler Reach Winery - The W Lovers 3pm
Northwest Brewing Pint and Pie - Live music 7pm
Vino Bella - Copastetic 7:30pm

Sunday

The Lime - Hearding Cats

Things to Do

Thursday 45°/41° Showers 🌧️

3rd Annual Optiv Holiday Toys-for-Tots Party in Bellevue

Tis the season to give! Bring an unwrapped toy for kids ages 6-16 and join the fun at Tavern Hall. With two drink chips in hand and all-you-can-eat food, you’ll feel like Santa with a buffet instead of a sleigh. Last year they filled five boxes of toys—this year, the goal is six. Let’s make it happen!
Time: 4-7 PM
Location: Tavern Hall, 505 Bellevue Square, Bellevue, WA
More Info: Learn More Here

Bring your holiday spirit and a generous heart—this party’s mission is bigger than the drinks and snacks!

Paint and Sip, Paint Party

Channel your inner Bob Ross (minus the fro) at this paint-and-sip event! With a brush in one hand and a cider in the other, you’ll create a masterpiece—or at least something fridge-worthy. No experience needed, just a willingness to have a great time and maybe get a little messy.
Time: 6:30-8:30 PM
Location: Locust Cider, 7425 166th Avenue Northeast, Suite C110, Redmond, WA
More Info: Learn More Here

Grab your friends and make it a night to remember. Picasso who?

Tall Timber Tune Wranglers

Put on your dancing shoes (or just show up in sneakers—this is casual) and join the Tall Timber Tune Wranglers for a night of fiddle tunes and square dancing. Don’t worry if you have two left feet; all dances will be taught, and the band’s toe-tapping beats will keep you moving.
Time: 6:30-8 PM
Location: Lodge at Beaver Lake Park, 25101 SE 24th St, Sammamish, WA
More Info: Learn More Here

Warning: you might accidentally become a square-dancing pro by the end of the night.

Friday 47°/44° Showers 🌧️

Complimentary Wine Sampling @ Issaquah: Sparkling Wine Sampling

Kick off your weekend with some fizz and sparkle! Enjoy a delightful array of sparkling wines, from bubbly Proseccos to classy Champagnes, all for free. It's like a wine holiday without the price tag—just remember, you must be 21 or older to indulge. If the event sells out, don’t worry; walk-ins are welcome to sip and savor the season.
Time: 6-7:30 PM
Location: The Wine Cellar Outlet, 710 Northwest Gilman Boulevard #Ste D104, Issaquah, WA
More Info: Learn More Here

Pro tip: Sparkling wine makes everything feel fancy, even if you’re just wearing holiday pajamas.

Tacky Sweater Murder Mystery Party

Put on your ugliest sweater and dive into a night of mystery, cocktails, and holiday hilarity. Someone will be "murdered," and it’s up to you and your fellow guests to solve the crime. With appetizers, two drink tickets, and a hilarious story to unravel, this adults-only event promises plenty of laughs and gasps.
Time: 6:30-9:30 PM
Location: Blakely Hall, 2550 Northeast Park Drive, Issaquah, WA
More Info: Learn More Here

Spoiler alert: The real crime would be missing out on this party.

Frosty Fest 2024

Sammamish’s most magical winter event is back! Frosty Fest has it all: live music from local school choirs, a holiday market with one-of-a-kind gifts, a photo booth, and—drumroll, please—REAL REINDEER. Bring the whole family and enjoy an evening packed with festive fun.
Time: 4-7 PM
Location: Sammamish City Hall Plaza
More Info: Learn More Here

If you’ve ever wanted to meet Rudolph’s cousins, this is your chance.

Saturday 49°/40° Showers 🌧️

Comedy! Lagers & Laughs: Casey McLain

Laugh the night away with headliner Casey McLain and a lineup of talented comedians at Northwest Brewing in Redmond. Pair the jokes with craft beer and pies for a night of laid-back hilarity. Casey’s humor blends the absurd and relatable, making it a perfect escape from holiday stress.
Time: 8-10 PM
Location: Northwest Brewing Pint & Pie Public House, 7858 Leary Way, Redmond, WA
More Info: Learn More Here

Side effects may include laughter-induced bellyaches and beer cravings.

Stride with Pride: Cherry Creek Falls Hike

Shake off the holiday stress with a peaceful hike to a stunning 25-foot waterfall. This 5-mile roundtrip trek has moderate elevation gain and a small creek crossing, perfect for nature lovers of all levels. Bring your day pack, layer up, and embrace the crisp December air.
Time: 10 AM
Location: Cherry Creek Falls Trailhead, 16538 Kelly Road Northeast, Duvall, WA
More Info: Learn More Here

Mother Nature called—she said this hike is the perfect holiday reset.

Yoga + Wine at Milbrandt Vineyards

Namaste and Chardonnay! Start your weekend with a 45-minute yoga class, followed by a glass of wine (or a bottle to share with friends). This all-levels class is perfect for stretching out holiday stress before settling into relaxation mode.
Time: 10:30 AM
Location: Milbrandt Vineyards Woodinville, 14450 Redmond-Woodinville Road Northeast, Woodinville, WA
More Info: Learn More Here

Wine after yoga—because you’ve earned it.

Needle-Felted Holiday Ornaments Workshop

Turn fluffy wool into adorable holiday ornaments at this crafty workshop. You’ll learn needle-felting basics and leave with a set of handmade decorations to wow your guests—or your tree. A $15 materials fee covers all supplies, and holiday bling is encouraged!
Time: 1-3 PM
Location: Picket Fence Art Studio, 14700 148th Ave NE, Woodinville, WA
More Info: Learn More Here

Warning: This workshop may lead to a new (and adorable) crafting obsession.

Sunday 46°/37° Showers 🌧️

Breakfast with Santa at the Woodmark Hotel & Still Spa

Start your Sunday with a festive breakfast the whole family will love! Enjoy a delicious menu while Santa himself visits to hear your holiday wishes and pose for priceless photos. With mimosas and holiday spirits available for the grown-ups, it’s a morning of magic and cheer. Book your preferred seating at 9:00 AM or 11:30 AM to secure your spot.
Time: 9 AM & 11:30 AM
Location: Woodmark Hotel & Still Spa, 1200 Carillon Point, Kirkland, WA
More Info: Learn More Here

Bring your camera, your appetite, and your holiday spirit for an unforgettable morning!

Village Wines Annual Bubbles Jam

Raise a glass to the holiday season at this sparkling wine extravaganza! Sample over 20 varieties of bubbles, including local gems and rare Champagnes, and enjoy a 15% discount on all wines tasted. Whether you’re a wine connoisseur or just love a good toast, this event promises to dazzle.
Time: 1-3:30 PM
Location: Village Wines, 14450 Redmond-Woodinville Road Northeast, Woodinville, WA
More Info: Learn More Here

Sip, savor, and sparkle—this is wine tasting at its bubbly best.

12Ks of Christmas

Don your Santa hat or reindeer antlers and join the fun at this holiday-themed run! Choose between the 12K, 5K, or Kids Dash, all set along the scenic waterfront in Kirkland. Whether you’re sprinting to win or just jogging for joy, it’s a festive way to stay active this season.
Time: 8 AM (Race start times vary)
Location: Marina Park, 25 Lakeshore Plaza, Kirkland, WA
More Info: Learn More Here

It’s the most wonderful run of the year—just don’t trip over your antlers!

Trivia

Which Issaquah theater venue is home to a popular annual film festival?

Answer to last week: Steel Mill

That’s it for this week. I missed the opening weekend of the Redmond Downtown park lights 🤦‍♂️. I don’t know about you, but when it’s raining all weekend, I just want to be inside somewhere warm.

See ya next weekend.