We like to host a variety of events at the winery. From game nights to wine pairing dinners our unique events make us one of Wisconsin’s best wineries to visit. Our events calendar is jam-packed with exciting events to fill your week with wine and fun. Select a day you are hoping to visit to see what’s happening or search in the keyword bar to look for cookie decorating classes, yoga, crafting, and other great experiences.
🎨 December Paint & Sip! 🍷
Join us from 5pm–7pm as Annie guides you step-by-step in creating this adorable painting of a marshmallow snowman soaking in hot cocoa!
Enjoy a fun, festive evening of sipping, painting, and bringing this cozy winter scene to life. ❄️☕️❤️
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 🐾🍷 Paws & Pours Donation Drive 🍷🐾 This November, we’re teaming up with the Humane Society of Southern Wisconsin to spread some love! ✨ How it works: Bring in any donation from their wish list, and you’ll get to pull a coupon from our special basket. You could win anything from a free bottle of wine to sweet discounts on your favorite products! 🌟 🐶 Most-needed items right now: Soft dog treats Wet cat food Dry and wet kitten food…
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🎶 Join us for an afternoon of live music with Sweet n' Sour Duo! 🎶Let their lively tunes set the mood as you sip on your favorite wine and enjoy the company of friends. Relax, unwind, and let the music carry you through a perfect day at the winery. With great vibes, delicious wine, and wonderful company, it’s the ideal way to spend your afternoon! |
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 🌿✨ Join us for our Wreath Workshop with Geske’s Garden! ✨🌿 Get into the festive spirit as Geske’s Garden guides you step-by-step through creating your very own beautiful wreath. 🎄 All materials will be provided — just bring your creativity (and maybe a friend or two)! 🍷 Let us pour you a glass of wine, grab your tickets, and get ready to craft your very own holiday masterpiece! get your tickets here |
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Join us for our Holiday Doormat Workshop! 🎅✨Get into the holiday spirit with a fun, hands-on evening of creativity and cheer! Craft and Vine will guide you step-by-step as you design and paint your very own festive doormat — the perfect way to welcome guests (and Santa!) to your home this season. Enjoy a glass of wine, relax, and let your creativity shine while you craft something truly one-of-a-kind.🎟️ Tickets are limited, so grab yours today before they’re gone! get… |
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Are you the ultimate Serena fan? A die-hard Blair stan? Or just obsessed with all the scandal, secrets, and drama of the Upper East Side? Then this is the event for you! Test your knowledge of iconic Gossip Girl moments, unforgettable quotes, and all the twists and turns that kept us hooked. Whether you know every Serena and Blair feud, Nate and Chuck drama, or Jenny’s schemes, this trivia challenge will put your expertise to the ultimate test. Come solo… |
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🎶 Join us for an unforgettable afternoon filled with live music, laughter, and vineyard views! Back2Back will be performing at Timber Hill Winery, bringing their signature sound to our cozy and scenic space. Sip your favorite wines, relax with friends, and soak in the beautiful surroundings — the perfect way to spend your day at the winery! 🍷✨ |
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🎄 Holiday Charcuterie and Wine Pairing Workshop 🎄 Join us for a festive and flavorful experience! Learn how to craft your very own holiday charcuterie board while enjoying a guided, hands-on class. Our team will share tips and tricks for building the perfect spread — just in time for the holiday season! ✨ Your Experience Includes: Hands-on instruction for creating your charcuterie board Educational session on the history and art of charcuterie Insight into why certain wines pair beautifully with… |
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 🎄 Join us at Timber Hill Winery for a holly jolly night of creativity and cheer! ✨ We’ll be painting winter-themed doormats that will make your front porch 🎁 merry and bright! Choose from designs like ❄️ snowflakes, “Welcome Winter” greetings, or add your own ✨sparkling touch✨ to make it uniquely yours. 🎨 No experience needed — all supplies are provided, and you’ll get easy, step-by-step instructions to guide you through your creation. 🍷 Sip your favorite Timber Hill wines,…  Tuesday Book Club has been cancelled due to unforeseen circumstances. We hope to see everyone on Thursday, December 11th at 6:00 PM instead! 📚✨ 📚 December Book Club 📚 Join us this December as we dive into Please Don’t Lie by Christina Baker Kline. Share your thoughts, hear different perspectives, and enjoy a cozy discussion with fellow book lovers. Don’t miss out on an evening of engaging conversation and literary fun! To make it easier for everyone to join the… |
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 🍷🎉 Join us for an evening of Wineo Bingo with the Milton Area Youth Center! Get ready to shout “WINEO!” every time you win and enjoy a fun night supporting a great cause. All donations to play will go directly to the Milton Area Youth Center to help support their amazing programs and the hard work they do for our community. Don’t miss out on the fun—and the chance to make a difference! |
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 🎅✨ Photos with Santa at Timber Hill Winery! ✨🎅 Santa is making a special stop at Timber Hill, and we’re inviting you to capture the magic! 📸 💲 Cost: $20 per family 📸 Includes: Up to 5 digital images 🍷 Please note: Photos do not include brunch. Brunch tickets may be purchased separately. 👉 Reserve your Photos with Santa spot here: https://timberhillwinery.square.site/ 👉 Grab your Brunch Tickets here:https://timberhillwinery.com/sunday-brunch-buffet/ Bring your smiles, your Christmas spirit, and your holiday cheer — it’s…
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Join us for live music with Evan Pingel! 🎶Cozy up and enjoy the warm, welcoming atmosphere of the winery as Evan fills the room with your favorite tunes. Sip on a glass of wine, catch up with friends, and let the music make your winter afternoon unforgettable! |
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 Vine and Dine: Five Course Food Pairing 🍷✨ Join us for an unforgettable evening of flavors, where exceptional cuisine meets exquisite wine. Our Vine and Dine experience features a thoughtfully curated five-course menu, each paired perfectly with Timber Hill Winery wines to elevate every bite. First Course – AppetizerSavor Prosciutto-Wrapped Asparagus with Lemon Aioli accompanied by tender Seared Scallops, paired with our crisp and refreshing White Fox Wonder. Second Course – SaladDelight in a Roasted Beet Salad with candied walnuts,… |
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 🎤🍷 December Comedy Night at Timber Hill Winery! 🍷🎤 Get ready for an evening full of laughs, fun, and good vibes! Join us as talented comedians take the stage, and sip on your favorite Timber Hill wines while you enjoy the show. Don’t miss out—grab your tickets today and secure your spot for a night of unforgettable comedy! Comedy Night seating is assigned! If you’re planning to sit with someone whose ticket you purchased separately, please email our Events Manager… |
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 🎄✨ Join us for a fun-filled Christmas Trivia Night at Timber Hill Winery! Test your knowledge on all things Christmas while enjoying a glass of your favorite Timber Hill wine. 🍷 Don your most festive (or fabulously ugly) sweater and get ready for an evening full of laughs, holiday cheer, and friendly competition. Make it a night to remember! |
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 🎄🔍 Join Us for the Murder at The North Pole Murder Mystery! Step into a world of holiday secrets and suspense as we uncover who’s naughty… and who’s deadly! Enjoy an evening of intrigue, laughter, and unexpected twists while sipping on your favorite Timber Hill wines. Can you solve the mystery before the final reveal? Tickets are priced at $55 per person and include the murder mystery game, and dinner. Wine and beer will be available for purchase. This event… |
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 Bouquets & Brunch! 💐✨ Grab your besties and join us for the ultimate girls’ day out at Timber Hill Winery! Create your own beautiful bouquet and enjoy a delicious brunch with your favorite people. 🌷 Build-A-Bouquet: $20 per person — includes all your supplies and flowers 🥞 Brunch & Drinks: Sold separately — reserve your brunch spot here https://timberhillwinery.com/sunday-brunch-buffet/ It’s the perfect way to sip, snack, and get creative together! get your tickets here
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Live Music with Bill Conway! 🎶Spend a cozy winter afternoon at the winery with the soulful sounds of Bill Conway. Let his music set the perfect mood as you sip on your favorite wine, relax with friends, and soak in the warm, inviting atmosphere. It’s the perfect way to unwind and make your winter day a little brighter! |
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 💚 Defy Gravity with Us at Our Wicked Celebration! 💚 Your $15 ticket includes: ⭐ Access to our Grazing Table — because there’s no place like home … or snacks ⭐ Entry into our Best Dressed Contest Come as your favorite Wicked character Whether you’re feeling Popular or ready to go full Elphaba green, show us your best spellbinding look The most “thrillified” costume wins the ultimate prize! Add-ons available (not included in ticket price): 💫 Hair Tinsel — shimmer like Glinda herself 💎 Permanent Jewelry — because style is forever, just like a good… |
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Join us for an unforgettable afternoon of live music with the incredibly talented Brooke Nunn! Let her captivating voice and energetic performance fill the winery with warmth and good vibes. Grab a glass of your favorite wine, unwind, and enjoy the perfect soundtrack to a relaxing day with friends and family. |
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 🍷🎄✨ Herd Social: Holiday Cocktail & Mocktail Creation Party! ✨🍸 Get into the holiday spirit with a festive night of creativity and cheer! For just $20, you’ll receive 📝 2 cocktail sheets to craft up to two custom holiday drinks — your choice of wine or liquor as the base! 🍷🥂 🎅 Here’s how it works: 👉 Choose your base (wine or liquor) 👉 Mix in your favorite syrups, garnishes & add-ons 👉 Our team gathers your ingredients 👉 Then it’s your turn to shake, stir & sip your merry creation!… |
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 🎨 December Paint & Sip! 🍷 Join us from 5pm–7pm as Annie guides you step-by-step in creating this adorable painting of a marshmallow snowman soaking in hot cocoa! Enjoy a fun, festive evening of sipping, painting, and bringing this cozy winter scene to life. ❄️☕️❤️ get your tickets here |
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Mark your calendars! 🗓️ Timber Hill Winery is turning upside down as we bring Stranger Things Trivia straight to you! Think you know Eleven, Mike, Dustin, and the rest of the gang better than anyone else? Come test your knowledge of Hawkins, the Upside Down, and all your favorite moments from the hit series. Bring your friends, grab a drink, and see who really rules the trivia world—Will it be you, or will the Demogorgon claim victory? Don’t miss out… |
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If you are looking for an event that is not listed on our calendar or have questions please send us an email at events@timberhillwinery.com.