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- We've got Oktoberfests, Fiesta Del Maiz, Grape Stomp, and a Stained Glass Workshop to name a few.
We've got Oktoberfests, Fiesta Del Maiz, Grape Stomp, and a Stained Glass Workshop to name a few.
🎉 Your Fall Bucket List Starts NOW: Stomp, Sip, Paint, Repeat!
Mike Surprenant
September 25, 2025 • Estimated Reading Time: 15 minutes
Fall is in full swing. If you’re into festivals, we’ve got some. If you’re into crafts, we’ve got that covered too. If you just want to catch a comedy show, yup, we’ve got that too! Avoid the Seattle traffic and parking headaches, Let’s dig into Eastsiders…
Table of Contents
Live Music 🎶
Thursday
425 Cellars - Mike Wayock 5:30pm
Locust Cider - Aidan Rufer 5pm
Goose Ridge - Steven Fletcher 5pm
Friday
Sparkman Cellars - Dueling Pianos 6pm
Prohibition Cellars - The Davanos 6pm
Woodin Creek Tasting Room - Billy Stapleton & Annie Eastwood 5pm
Chelan Ridge Winery - Alex Britton 5pm
Obelisco - Brian James 5pm
Northwest Spirits - Soulcem Acoustic Duo 6pm
Northwest Cellars - Kim Maguire & David Joyner 5pm
Wine Me Up - Harmonious 8pm
Saturday
Page Cellars - Whisky Trail 1pm
Gard Vinters - Scott Lindenmuth 2pm
Chelan Ridge Winery - Jade Teather 5pm
Terry’s Kitchen - Philip Woo 7pm
Bakes Place - Moondance 8:30pm
Vino Bella Wine Bar - Distant Station 7:30pm
Sunday
425 Cellars - Jarrett Renshaw 3:30pm
Weekend Fix 🥳
Thursday Sept 25th 66°/51° 🌤️
🎤😂 Pom Does Comedy Season Two Kick-Off Show! 🍷🎭
Get ready to LOL your socks off! Pomegranate Bistro is serving up laughs, libations, and a whole lotta good vibes to launch Season Two of Pom Does Comedy. Whether you're showing up solo, dragging your friends, or turning it into a romantic giggle-fest, there's a seat (or a barstool) with your name on it. There's a $30 food/drink minimum—but hey, zero-proof cocktails mean even your designated driver can be fancy. Bonus: this show sells out, so don’t snooze or you’ll lose!
🕒 Time: 6:00 PM
📍 Location: Pomegranate Bistro, 18005 NE 68th St #A-150, Redmond, WA
🔗 More Info: HERE ✅
Don’t miss a night packed with flavor, laughter, and probably someone snorting wine through their nose. 🍇🍸
🏈🍷 Touchdowns & Tastings: Seahawks Watch Party! 🧀🏟️
It’s game day—but make it classy. Join fellow football fanatics at Upchurch’s Woodinville tasting room for a private watch party where touchdowns meet charcuterie. Your ticket includes 2 glasses of wine and a tasty board, so you can sip and snack while you cheer (or cry) for the Seahawks. Kickoff is at 5:15 PM, but the doors open at 4, so get there early to pre-game like a grape-loving pro!
🕒 Time: 4:00 PM
📍 Location: Upchurch Vineyard, 14455 Redmond-Woodinville Rd NE #Suite A, Woodinville, WA
🔗 More Info: HERE ✅
Wine, football, and cheese? Now that’s what we call a winning lineup. 🧀🍇🏈
🎨🍹 Paint, Sip & Island Vibes at Pasifika! 🌴🎨
Calling all aspiring Picassos and cocktail connoisseurs—this night’s for you. Unleash your inner artist with Kay the Paint Lady while basking in the tropical glow of Pasifika Grill & Bar. Whether you're an expert or your last painting was a stick figure, this guided experience makes art fun and foolproof. Light bites are on the house, drinks are available to order, and laughter is pretty much guaranteed.
🕒 Time: 6:00 PM
📍 Location: Pasifika Grill & Bar, 625 116th Ave NE, Bellevue, WA
🔗 More Info: HERE ✅
Come for the paint, stay for the vibes—and leave with a masterpiece! 🖌️🍸🌺
👩🎨👨👧👦 Family Paint Night: Masterpieces & Memories! 🎨❤️
Looking for a fun family night that doesn’t involve stepping on Legos or dodging glitter bombs? Join this paint party where kids and grown-ups alike can create beautiful 16"x20" canvas art together. Paints and good vibes are provided—just bring your creativity (and maybe a snack or two).
🕒 Time: 6:30 PM
📍 Location: Five Iron Golf, 425 Urban Plaza Suite 200, Kirkland, WA
🔗 More Info: HERE ✅
Bring the fam, paint some art, and make fridge-worthy memories. 🖼️👨👩👧👦🎉
Friday Sept 26th 69°/52° 🌤️
🍷🎉 BINGO Madness at Village Wines! 🎲🍇
Grab your lucky dauber and your wine-loving crew—it’s BINGO night, baby! Village Wines is turning game night up to 11 with prizes, reusable bingo cards, and all the food and vino you can handle. Ten games, one fabulous night, and possibly a dramatic victory dance in your future.
🕒 Time: 8:00 PM
📍 Location: Village Wines, 14450 Redmond-Woodinville Rd NE, Woodinville, WA
🔗 More Info: HERE ✅
Sip, dab, win—then shout BINGO like you mean it. 🍷🎯💃
🎤🍷 Big Laughs Incoming: Duane Goad LIVE! 😂🎉
Cozy Comedy is back and bringing the heat with national headliner Duane Goad—aka the king of clever sarcasm. He’s toured across the U.S. and Canada, opened for comedy royalty, and now he’s ready to make you laugh so hard your wine comes out your nose. Also featuring the sharp wit of rising star Jeremiah Hughes! Seats are limited, so don’t sleep on this comedic goldmine.
🕒 Time: 7:00 PM
📍 Location: Warr-King Wines, 19501 144th Ave NE #D700, Woodinville, WA
🔗 More Info: HERE ✅
Snag your seat and get ready for the funniest night of your week—cheers to comedy and cabernet! 🍷🎭
🐦🌇 Bird Watching at Dusk: Feathers & Fun! 🔭🦉
Trade your screen time for some sky time and discover the nightlife of... birds! Whether you're a binocular-wielding pro or just here for the sunset vibes, this chill evening of feathered fun is perfect for all experience levels. Binoculars will be provided (while supplies last), but feel free to bring your own and a curiosity for the wild side of twilight.
🕒 Time: 6:00 PM
📍 Location: Innovation Hall 111, 110th NE, Bothell, WA
🔗 More Info: HERE ✅
Spread your wings and join the flock for an evening that’s part nature, part magic. 🐤🌆🔭
Saturday Sept 27th 73°/54° 🌤️
🍺🎉 Bellevue Oktoberfest Bar Crawl Bonanza! 🥨💃
Break out the lederhosen and prepare to crawl (responsibly) through Bellevue’s best bars! This isn’t your grandma’s Oktoberfest—it’s a wild, beer-fueled bash complete with live entertainment, exclusive drink specials, and even an after-party that’ll keep the night hoppin’. Grab your wristband, follow the digital map, and prost your way through the city like a true brew legend!
🕒 Time: 4:00 PM
📍 Location: Multiple Bars & Venues, Bellevue, WA
🔗 More Info: HERE ✅
Cheers to steins, friends, and unforgettable beer-filled memories! 🍻🎶🗺️
🪓🥞 Paul Bunyan Breakfast Bash: Flapjacks & Fierce Chops! 🌲💪
Calling all lumberjacks (and those who just like carbs): come hungry and ready to compete! Enjoy FREE pancakes (yes, you read that right), then test your wood-splitting skills in a friendly competition for all ages. Bring your axe, your appetite, and your A-game—because the logs aren’t going to split themselves!
🕒 Time: 9:00 AM
📍 Location: Amblewood, 5030 288th Ave NE, Redmond, WA
🔗 More Info: HERE ✅
Axes, syrup, and glory—what more do you need for a legendary morning? 🪓🥞🏆
👟🎉 5K Fun for a Cause: Operation School Bell Run/Walk! 🏃♀️💖
Put the “fun” in fundraising with this feel-good 5K! Whether you run, walk, or shuffle while sipping coffee, your steps help local students get the essentials they need to succeed. Flat course, finisher medals, and free shirts for early birds—plus music and post-race good vibes!
🕒 Time: 9:00 AM
📍 Location: Marymoor Park Field #5/Lot K, 6046 W Lake Sammamish Pkwy NE, Redmond, WA
🔗 More Info: HERE ✅
Get your heart pumping for a heartwarming cause—sneakers optional but highly encouraged. 👟🎽🎶
🌽💃 Fiesta del Maíz: Culture, Corn & Celebration! 🎭🌮
Get ready for a cultural explosion where corn takes center stage (yes, really)! Fiesta del Maíz honors Mesoamerican Indigenous traditions with a day full of Aztec dancers, delicious food, vibrant art, and educational workshops. It’s a flavorful fusion of history and community that’ll leave your heart (and belly) full. Bonus points if you wear something colorful and festive!
🕒 Time: 11:00 AM
📍 Location: Crossroads Community Park, 999 164th Ave NE, Bellevue, WA
🔗 More Info: HERE ✅
Come for the culture, stay for the tacos—and don’t forget to dance! 🌮🕺🔥
🎃👨👩👧 Pumpkin Buddies Family Workshop! 🎨🍂
Forget carving—this is clay pumpkin creation, and it’s cuter than a PSL in fall. Kids and adults alike will love this hands-on workshop where you’ll mold, shape, and glaze your very own pumpkin pals. Whether you're making one or a full pumpkin patch, it's a cozy, crafty way to kick off autumn vibes.
🕒 Time: 11:00 AM
📍 Location: Eastside Pottery – Bellevue, 1809 130th Ave NE #124, Bellevue, WA
🔗 More Info: HERE ✅
Make something gourd-geous with the fam—it’s fall fun in 3D! 🎃👩🎨🍁
🌀🖋️ Mandala Art Workshop: Draw, Breathe, Repeat! 🧘♀️🎨
Ready to get in your zen zone? This meditative workshop teaches the art of mandala drawing—symmetrical, beautiful designs that radiate calm. Taught by local artist Priya Mutha, you’ll get step-by-step guidance and all the supplies you need. No experience? No problem. Come for the mindfulness, stay for the pretty patterns.
🕒 Time: 2:00 PM
📍 Location: Happy Time Studio, 157 Front St N, Issaquah, WA
🔗 More Info: HERE ✅
Soothe your soul and sharpen your pen—mandala magic awaits! 🌀🖊️✨
🍇👣 Grape Stomp & Harvest Party: Get Stompy With It! 🍷💃
Ready to squish grapes like a pro and laugh until your feet are purple? Maryhill Winery is bringing back its annual grape stomp, and you're invited to join the messy, joyous fun. Step into barrels, stomp your heart out, sip some wine, and leave with a stained shirt and a brag-worthy story. It’s hands-on, feet-first harvest happiness!
🕒 Time: 2:00 PM
📍 Location: Maryhill Winery, 4810 NE 145th St #A, Woodinville, WA
🔗 More Info: HERE ✅
Come squish, sip, and stomp your way into wine history—no shoes required. 🍇👣🍷
🍺🎶 Oktoberfest Weekend at Moss Bay Hall: 2 Days of Bavarian Mayhem! 🥨🥳
Day 1 is all steins and shenanigans with keg tapping, live music, and classic games like Hammerschlagen (look it up—you’ll love it). Day 2 brings the family fun with face painting, balloon animals, and mini stein-holding champs. Whether you're lederhosen-deep in pretzels or tossing beanbags with your kids, this Oktoberfest is packed with Kirkland-style cheer.
🕒 Time: Noon (both days)
📍 Location: Moss Bay Hall, 111 Central Way, Kirkland, WA
🔗 More Info: HERE ✅
Two days. One roof. Infinite beer-fueled fun. Bring the crew and raise a stein! 🍺🎈🎸
🎊🇲🇽 Hispanic Heritage Celebration: Music, Culture & Joy! 💃🎉
Celebrate the vibrance of Hispanic heritage with an afternoon full of music, cultural experiences, and family-friendly fun. It’s a joyful gathering at The Village at Totem Lake, and you’re invited to dance, explore, and connect. No passport required—just bring good vibes and comfy shoes!
🕒 Time: 2:00 PM
📍 Location: The Village at Totem Lake, 11901 NE Village Plaza, Kirkland, WA
🔗 More Info: HERE ✅
From salsa beats to tasty treats—this is one fiesta you won’t want to miss! 🎶🌮🎈
Sunday Sept 28th 71°/54° ☁️
💃🔥 Pole Dance Party/Mixer: Spin, Sip & Slay! 💪💄
It’s time to ditch the gym and get fabulous. Whether you're new to the pole or just here for the party, this beginner-friendly class has it all—warm-ups, dance moves, and plenty of fun. You'll make new friends, try something daring, and maybe discover a new favorite hobby (or alter ego). No dance experience needed, just a willingness to werk it.
🕒 Time: Noon
📍 Location: Trinity Pole Studio, 12089 124th Ave NE, Kirkland, WA
🔗 More Info: HERE ✅
Come twirl, laugh, and leave feeling like Beyoncé. 👠✨💃
🎨🍕 Artvana Paint & Sip: Monet... But Make It Fun! 🖌️🍷
This isn’t your average paint night—it’s Artvana's “Monet Mix Up,” and it's all about creating a masterpiece while sipping wine at a self-pour bar. With pizza in one hand and a brush in the other, you'll be guided step-by-step by a pro artist in a relaxed, laughter-filled atmosphere. No stress, just swirls and snacks.
🕒 Time: 1:00 PM
📍 Location: The Redd Dog, 10598 NE 10th St, Bellevue, WA
🔗 More Info: HERE ✅
Sip, paint, and Monet your way to masterpiece status. 🍕🎨🍷
🧱🍂 Fall Vibes LEGO® Bulk Smash: Brick It Like It's Hot! 🪣🧱
Challenge: how much LEGO can you cram in a one-gallon bucket? Answer: a ridiculous amount, if you’re good at it! Come let loose at this family-friendly bulk smash event. It’s part game, part puzzle, and totally satisfying for brick-lovers of all ages. Build your fall collection and get creative with pure LEGO chaos.
🕒 Time: 6:00 PM
📍 Location: Bricks & Minifigs, 1490 NW Gilman Blvd, Issaquah, WA
🔗 More Info: HERE ✅
Smash, scoop, and score big in the most colorful challenge of the season! 🍁🧱🎉
🌄✨ Stained Glass Workshop: Sunset Vibes in Glass! 🖼️🔥
Trade your screen for stained glass and create your very own sunset mountain masterpiece! In this beginner-friendly workshop, you’ll learn everything from foiling to soldering to polishing—basically, all the shiny magic. With expert guidance and all materials included, you’ll walk away with a glowing piece of art (and possibly a new obsession).
🕒 Time: 4:00 PM
📍 Location: 301 W North Bend Way Suite 100A, North Bend, WA
🔗 More Info: HERE ✅
Shine bright, solder bold, and take home more than just good vibes—take home art! 🧡🪟🌄
Trivia 🤔
Issaquah was originally founded as a ________ town.
Last Weeks Question and Answer:
Redmond’s City Hall includes an outdoor public art gallery featuring works by local artists. What is it called? The “Art Reach Gallery”
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