📅 Plans? You Do Now. These Events Are Too Good to Skip!

From comedy nights to sailgating to wine trains, these are the can't-miss happenings you’ll regret not attending on your Labor Day weekend!

Author

Mike Surprenant
August 28, 2025 • Estimated Reading Time: 15 minutes

It’s a hot one! But, we’ve got rain coming this weekend, so it’ll cool down a bit. Why can’t we have 3 day weekends every weekend!? Skip the Seattle traffic and parking headaches and dig in. Let’s get to it…

Table of Contents

Live Music 🎶

Thursday

Willows Lodge - Jarrett Renshaw 6pm
425 Cellars - Goldy and Foss 5:30pm
Locust Cider Woodinville - Aidan Rufer 5pm
Goose Ridge - Bec Lynn 5pm

Friday

Prohibition Cellars - Great American Train Wreck 6pm
Woodin Creek Tasting Room - Ali Diane 5pm
Chelan Ridge Winery - Aidan Rufer 5pm
Obelisco - Jeremy’s Chicken & Booke Richey 5pm
Milbrandt Vineyards - Josiah Bogle 5pm
The Lime - Eden 9:30pm
Wine Me Up - Lucia Flores-Wiseman 8pm

Saturday

Gard Vintners - Jaeden Luke 3pm
Obelisco - Nick Mardon 7pm
The Lime - Diamond Star Halo 9pm
Northwest Cellars - Midnight Cafe 5pm

Sunday

Chelan Ridge Winery - Tyler Mcginnis 4pm
Locust Cider Woodinville - Ian Skavdahl 1pm

Weekend Fix 🥳

Thursday Aug 28th 82°/61° 🌤️

National Thoughtful Day

🎨 Sip, Swirl, and Splatter: Paint Nite is Here! 🖌️🍷


Ready to unleash your inner Picasso without the pressure? Join this laugh-filled, brush-dipping adventure where you’ll create your own masterpiece—no experience required, but sass is highly encouraged. You'll get a 16"x20" canvas, all the paints you need, and vibes strong enough to cancel your art school regrets. While food and drink aren’t included, you’re totally allowed to munch and sip as you paint—yes, wine makes the clouds look better.
🕒 Time: 6:30 PM
📍 Location: Five Iron Golf, 425 Urban Plz Suite 200, Kirkland, WA
🔗 More Info: HERE ✅
Grab a brush, sip something fun, and let’s make questionable art decisions together! 🎨✨

🎬 Galaxy Vibes & Free Popcorn: Outdoor Movie Night! 🌌🍿

Grab your lawn chair, assemble your crew, and prepare for an epic night under the stars with Guardians of the Galaxy Vol 2! The Spring District is transforming into a family-friendly fun zone, with a pop-up market, food trucks, a magic show, and face painting—all before the movie even starts. Once the sun sets, the galaxy-saving action begins on the big outdoor screen. Bonus: it’s totally FREE, so your wallet can relax while your heart races with Marvel-level excitement.
🕒 Time: 3:00 PM – 10:00 PM
📍 Location: 12167 NE 14th Terrace, Bellevue, WA
🔗 More Info: HERE ✅
Bring a blanket, grab some snacks, and come watch the stars—on screen and in the sky! 🌠🎥

🎶 Sunset Grooves: Evening Summer Concerts by the Lake 🎤🌅

Nothing says summer like live music, golden skies, and friends by your side. These Thursday evening concerts bring the beats to the beautiful shores of Lake Washington—so come ready to sway, snack, and socialize. Whether you’re a dancer, a toe-tapper, or just here for the vibes, this weekly concert series is a certified good time. Oh, and did we mention it’s FREE? So really, no excuses.
🕒 Time: 7:00 PM
📍 Location: Marina Park, 25 Lakeshore Plaza, Kirkland, WA
🔗 More Info: HERE ✅
Bring your picnic blanket, your besties, and your best air guitar. 🎸✨

🚂 All Aboard the Snoqualmie Valley Wine Train! 🍷🚆

Choo-choose your adventure with this one-of-a-kind wine-tasting train ride through the scenic Snoqualmie Valley! Sip local wines, nibble on gourmet bites, and enjoy stunning views—all while gliding through history on the Northwest Railway Museum’s vintage train. Your ticket comes with a souvenir wine glass and 8 tasting tokens to use at your own delicious discretion. Must be 21+ because this ride pours more than just scenery.
🕒 Time: 4:30 PM
📍 Location: Northern Railway Museum, 38625 SE King St, Snoqualmie, WA
🔗 More Info: HERE ✅
Ride, sip, and repeat—it’s like Napa, but with train whistles! 🚂🍇

🔥 Smoke & Oak: Wine, BBQ, and Western Nights 🤠🍖

Saddle up for a smoky, music-filled evening at the winery where BBQ meets bold reds under the stars. Winemaker Todd Krivoshein is manning the grill (cape optional), and live local music will keep your boots tappin’ all night long. With a killer lineup of performers, cold drinks, and surprise treats, this is more than just a wine night—it’s a full-blown summer sendoff party. Tickets go fast, so don’t be the one crying into your empty wine glass.
🕒 Time: 6:00 PM
📍 Location: Page Cellars, 19495 144th Ave NE, Woodinville, WA
🔗 More Info: HERE ✅
Come for the BBQ, stay for the band, and raise a glass to summer’s greatest hits! 🎶🍷

Friday Aug 29th 86°/60° 🌤️

National Lemon Juice Day

😂 A Funny Finish: Comedy Night with Scott Losse 🎤🤣

Get ready to LOL with the Pacific Northwest’s favorite comedy dad—Scott Losse! With over 100K Instagram fans and a face made for comedy (and probably trouble), Scott is bringing his relatable hilarity and awkward charm to Woodinville for one night only. He’s been on big stages like SF Sketchfest and Bumbershoot, but now he’s back where it all began—right here, with you and your wine glass. This is the kind of funny you don’t want to miss.
🕒 Time: 7:00 PM
📍 Location: Warr-King Wines, 19501 144th Avenue Northeast #D700, Woodinville, WA
🔗 More Info: HERE ✅
Seats are limited and the laughs are guaranteed—get yours before it’s standing room snickers only! 🎟️🍷

🎙️ Wine Meets Wit: Stand-Up with Meaghan Elwood 🍷😆

Brace yourself for wine-fueled laughter as comedy queen Meaghan Elwood takes the stage at Alluvium Cellars! She’s a mom-turned-mic-dropper who turns chaos into comedy gold, covering everything from dating disasters to surviving parenthood. Local legend Barbie Collins Young joins her with sharp, self-aware jokes and a name she’s still recovering from (Barbie, really?). Food truck, great wine, and belly laughs—what else do you need?
🕒 Time: 7:00 PM
📍 Location: Alluvium Cellars @ The Junction, 19151 144th Avenue Northeast #Space J, Woodinville, WA
🔗 More Info: HERE ✅
Pull up, pour a glass, and prepare to laugh ‘til your cheeks hurt! 🥂😂

🥾 Guided Hike for Seniors: Nature with a Side of Chill 🌲👟

Take a stroll, not a slog, on this peaceful 2.5-mile guided loop made just for senior hikers. The trail is flat, the vibes are relaxing, and the fresh air is guaranteed to be better than your usual Tuesday routine. Bring some water, snacks, and your favorite walking poles—and come get your steps in with great company and great views. Just $5 to trade screens for streams.
🕒 Time: 9:00 AM
📍 Location: Issaquah Senior Center, 75 N.E. Creek Way, Issaquah, WA
🔗 More Info: HERE ✅
Lace up those comfy sneakers and let’s take it slow—and scenic! 🌿👣

Saturday Aug 30th 75°/58° 🌧️

National Toasted Marshmallow Day

🎉 Woodinville Summer Family Day: Food, Fun & Freebies! 🍦🎶

Get ready for the ultimate family block party, packed with free food, ice cream, live music, and giveaways! Bring the kids, bring the cousins, bring your neighbor who never returns your Tupperware—everyone’s welcome. There’ll be a school supply donation drive, a book bag giveaway, and a whole lot of summer joy jammed into one park. Pro tip: the beats from Soul Summit Music will make you dance like no one’s watching (but everyone totally is).
🕒 Time: 1:00 PM – 6:00 PM
📍 Location: DeYoung Park, 13680 NE 175th Street, Woodinville, WA
🔗 More Info: HERE ✅
Don’t miss this day of free family fun—you’ll be the hero of the weekend! 🎉👨‍👩‍👧‍👦

🛍️ Treasure Hunt Time: Community Rummage Sale 💸🪙

Calling all bargain hunters, antique lovers, and garage sale warriors—this is your moment! The 3rd Annual Community Rummage Sale at the Eagles Lodge is your chance to uncover hidden gems, quirky collectibles, and stuff you never knew you needed (but absolutely do). Bonus: there’s a 50/50 raffle where you could win up to $2,500. That’s a lot of lattes and lava lamps.

🕒 Time: 1:00 PM – 6:00 PM
📍 Location: Eagles Lodge, 175 Front St N, Issaquah, WA
🔗 More Info: HERE ✅
Bring cash, good vibes, and an empty trunk—you’re gonna find something! 🛍️💥

🌍 Ubuntu Nerudo Cultural Festival: Food, Dance & African Vibes 🌿🪘

Step into a vibrant celebration of African heritage, music, cuisine, and community at the Ubuntu Nerudo Cultural Festival! This free event serves up soulful bites, energetic dancing, and games for the whole family—plus a message of unity that’s as inspiring as the drum beats. Hosted by Ubuntu Nerudo African Heritage, this festival honors the spirit of “I am because we are.” Translation: come ready to connect, celebrate, and snack.
🕒 Time: 12:00 PM
📍 Location: Lake Sammamish State Park, 2000 NW Sammamish Rd, Issaquah, WA
🔗 More Info: HERE ✅
Get your groove on and experience a culture-rich celebration that feeds the soul. 💃🏾🍲

🏈 Husky Football Sailgate: Cruise into Game Day! 🚢💜

Forget tailgating—this is sailgating, and it’s the most elite way to arrive at Husky Stadium! Hop aboard an Argosy Cruise from Carillon Point and float your fandom to kickoff while sipping drinks and soaking up lake views. Whether you're a season-pass diehard or just in it for the snacks and selfies, this pre-game voyage is how real Dawgs roll. Bonus: you get to skip traffic like an absolute legend.
🕒 Time: 6:00 PM
📍 Location: Argosy Cruises, 4500 Carillon Pt, Kirkland, WA
🔗 More Info: HERE ✅
Score major points with your squad—this is the ultimate Husky fan flex! 🐾⛴️

🚘 Exotic Car Show: Chrome Dreams & Engine Roars 🏎️✨

Vroom into the weekend with the largest weekly exotic car gathering in the U.S.—yep, the Exotics at RTC! This event is your chance to gawk at ridiculously rare rides, mingle with fellow gearheads, and inhale that sweet, sweet scent of burning rubber and ambition. Saturdays, weather permitting, Center Court transforms into a glittering grid of automotive envy.
🕒 Time: 9:00 AM – 11:00 AM
📍 Location: Redmond Town Center, 7525 166th Ave NE, Redmond, WA
🔗 More Info: HERE ✅
Polish your shades and prepare for car envy—this one’s horsepower heaven! 🏁😎

💃 KAW Summerfest: Dance Like Nobody's Judging 💫🎶

Join the joyful chaos of KAW Summerfest where rhythm rules and everyone’s a dancer! Whether you’re twirling in traditional attire or freestyle flailing to the beat, this Mega Thiruvathira event is all about fun, community, and making memories. No experience necessary—just bring your smile, some enthusiasm, and maybe backup snacks.
🕒 Time: 2:00 PM
📍 Location: Perigo Park, 9011 196th Ave NE, Redmond, WA
🔗 More Info: HERE ✅
Put on your happy feet and join the swirl—this is joy in motion! 🥰🕺

Sunday Aug 31st 74°/58° 🌦️

National Trail Mix Day

🎶 Confluence Music Festival: Art, Beats & Summer Magic 🎨🎸

Get ready for a five-hour symphony of music, art, and pure summer joy at the 7th Annual Confluence Music Festival! Set in beautiful downtown Issaquah, this festival brings together local legends and global talents on one vibrant stage. From live performances to artisan vendors, food trucks, and even violins turned into visual art (yes, really), this is the cultural block party of the season. Bonus: it’s free, but a $10 donation gets you good karma and festival cred.
🕒 Time: 2:00 PM – 7:00 PM
📍 Location: Confluence Park, 595 Rainier Blvd N, Issaquah, WA
🔗 More Info: HERE ✅
Come for the vibes, stay for the violins-turned-masterpieces—this fest hits all the notes! 🎻🌞

📸 Botanical PhotoWalk: Bloom Where You Snap! 🌺📷

Step into a floral wonderland and learn to shoot like a pro with travel photographers John and Lisa Merrill! This garden PhotoWalk at Bellevue Botanical Garden is part nature escape, part photography class, and 100% a treat for your creative soul. Whether you're toting a DSLR or just your phone, you’ll explore light, color, and composition like a seasoned shutterbug. Bonus: there's a follow-up Zoom to share your pics and humblebrag.
🕒 Time: 7:00 AM
📍 Location: Bellevue Botanical Garden, 12001 Main Street, Bellevue, WA
🔗 More Info: HERE ✅
Capture nature, chase the light, and become that artsy friend with all the amazing photos! 🌿📸

🚶‍♀️ Hike for Humanity: Walk With Purpose, Step With Love 💚🥾

This isn't just a hike—it's a mission. Join a heartfelt walk through Rattlesnake Ledge to raise funds for victims of famine and genocide in Sudan and Somalia. With every step, you’ll be helping ARAHA provide urgent aid where it's needed most. Afterward, share a lakeside picnic with a community of changemakers. Children under 12 hike free, and every ticket is a donation in motion.
🕒 Time: 10:30 AM
📍 Location: Rattlesnake Ledge Trailhead, Snoqualmie Valley Trail, North Bend, WA
🔗 More Info: HERE ✅
Walk with purpose—because together, our steps create real change. 🌍❤️

🧘 Aerial Yoga Workshop: Get Your Zen Off the Ground 🧘‍♀️🕊️

Ditch the mat and hang out—literally! This aerial yoga workshop will have you floating in silk hammocks as you stretch, decompress, and rediscover your playful side. Whether you’re a seasoned yogi or just looking to feel like a superhero on a rest day, this class will leave you feeling light, centered, and wonderfully upside down. Bonus: final savasana happens in a silky cocoon. Yes, please.
🕒 Time: 10:00 AM
📍 Location: Be One Yoga, 11220 NE 124th St, Kirkland, WA
🔗 More Info: HERE ✅
Float, fly, and feel fabulous—your inner child and spine will thank you! 💫🧘‍♂️

Trivia 🤔

Which Eastside city is famous for its carillon chimes in the downtown park?

Last Weeks Question and Answer:
Which Kirkland public park is known for a tree lighting ceremony during the holidays? Marina Park

How'd you like the newsletter today?

Your feedback helps us make the best newsletter possible.

Login or Subscribe to participate in polls.