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.
🎶 Live Music with Trevor O’Connor 🎶
Join us at Timber Hill Winery for an afternoon of live music with Trevor O’Connor from 2:00 PM–4:00 PM. Grab a glass of your favorite wine, cocktail, mocktail, or beer, relax, and enjoy great music in a beautiful vineyard setting. We hope to see you there!
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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: $25 per person — includes all your supplies and flowers. Your ticket also reserves your spot for brunch. Brunch & Drinks: Sold separately the day of the event. Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your…
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 Join us for a relaxing afternoon of live music with Back2Back Trio from 2–4 PM! Settle in with your favorite glass of wine and enjoy smooth acoustic sounds, great vibes, and beautiful vineyard views. Whether you’re stopping in for a tasting, gathering with friends, or just looking for a laid-back Sunday escape, this is the perfect way to spend your afternoon at Timber Hill. |
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 Your next obsession just dropped... 📺🍷 Grab your fellow binge-watchers and join us for Reality TV Trivia! We'll be testing your knowledge across five drama-filled rounds: 🍸 Bravo favorites ❤️ Dating show drama ✨ Celebrity reality 📺 Reality competition & game shows 🔥 Today's biggest binge-worthy hits Whether you've kept up with the Kardashians, survived Scandoval, know exactly who got "a text," or never miss the latest reality TV buzz, there's something for every fan. Pour yourself a glass, gather… |
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 Step behind the scenes and discover the story behind every sip. Behind the Vines is a customized, guided wine tasting designed to immerse you in the heart of Timber Hill Winery. Led by one of our knowledgeable wine guides, guests will be thoughtfully guided through four hand-selected wine samples, each chosen to highlight the diversity and character of our wines. Your tasting is paired with a curated charcuterie cone to perfectly complement the experience. Following the tasting, guests will enjoy… |
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 Join us for the ultimate curated secondhand shopping event! Thriftfest Midwest is a curated vintage, secondhand, and handmade clothing market focusing on sustainability and artistic expression. Shop from the areas best secondhand clothing vendors from Vintage shops to handmade and upcycled accessories. This is an event you do not want to miss! We will have activities, snacks, and over 20 clothing and accessories vendors. This event will be located on the vineyard of Timber Hill with the most stunning view.…
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🎶 Live Music with Trevor O'Connor 🎶 Join us at Timber Hill Winery for an afternoon of live music with Trevor O'Connor from 2:00 PM–4:00 PM. Grab a glass of your favorite wine, cocktail, mocktail, or beer, relax, and enjoy great music in a beautiful vineyard setting. We hope to see you there! |
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 🍨 Cool off with the sweetest Herd Social of the summer! ☀️ Join us for our Build Your Own Ice Cream Social and create your dream sundae! Start with your choice of chocolate or vanilla ice cream 🍦, then pile on your favorite toppings, syrups, whipped cream, cherries 🍒, and more to make it uniquely yours. Your ticket includes everything you need to build two custom sundaes, so come hungry and get creative! Whether you keep it simple or load up on every topping in sight, it's… |
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 🎉 Purse Bingo Night! 🎉 Join us for a fun-filled evening of Purse Bingo, where all prizes are stylish purses! 👜✨ For just $25, you can play as many rounds as we can fit from 5:30 PM – 7:00 PM. ⏰ Can’t make it at 5:30? No worries! Jump in at the next starting round—don’t miss the fun. 🎟️ Tickets are required, so grab yours today and get ready for a night of prizes, laughs, and good times! Disclaimer: If… |
1 event, 🍷 Join us for Wineo Bingo benefiting the Humane Society of Southern Wisconsin! 🐾 All donations to play go directly toward supporting their mission of helping pets go home. ❤️ Enjoy an evening of wine, bingo, fun, and prizes while making a difference for animals in our community! 🐶🐱🎉 |
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 🎵 Live Music with Matt Jaye 🎵 Spend your Sunday afternoon at Timber Hill Winery enjoying live music from Matt Jaye from 2:00 PM–4:00 PM. Pair great tunes with your favorite wine, cocktail, mocktail, or beer and soak in the relaxing vineyard atmosphere. |
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 🧠🍷 Grab your friends and put your knowledge to the test at Pub Trivia! Join us from 6:00pm–7:00pm for a fun evening of friendly competition, laughs, and great wine. Whether you're a trivia pro or just in it for the fun, everyone is welcome. Gather your team, enjoy your favorite drinks, and see if you have what it takes to claim bragging rights! |
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 We’re excited to announce our Annual Carnival! 🎪✨ Join us from 12:00 PM–4:00 PM for a day packed with fun, games, music, and family-friendly excitement! 🎯 Carnival Activities • Balloon Pop • Ring Toss • Duck Pond with a Twist featuring Rubber Ducky Winery 🦆 • Bounce House • Dunk Tank 💦 • Temporary Tattoos • Face Painting • Permanent Jewelry by Anastasia • Flower Bar 🌸 • Caricature Artist ✍️ • Puppy Kissing Booth featuring Be My Furever 🐶 • Aerial Acrobats… |
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 🥩🎉 Join us for a Meat Raffle benefiting the Milton Junction Cemetery Association! Bring your friends, grab your favorite drink, and get ready for an evening of fun, prizes, and plenty of chances to win delicious meat packages—all while supporting the Milton Junction Cemetery Association and their mission. Whether you're feeling lucky or just looking for a great night out, this is an event you won't want to miss. See you there! |
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 📖 August Book: American Fantasy by Emma Straub 📚✨ Book Club at Timber Hill Winery – August Edition ✨📚 Join us this August for Book Club as we gather to discuss American Fantasy by Emma Straub! Whether you’re a seasoned reader or just getting back into the habit of picking up a good book, everyone is welcome. This is a relaxed, welcoming space to unwind, connect, and enjoy thoughtful conversation with fellow book lovers—all while enjoying your favorite Timber Hill… |
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 🎶 Join us for an evening of Live Music with Duane Worden at Timber Hill Winery! From 6:00 PM–8:00 PM, Duane will take the stage, providing the perfect soundtrack for your evening. Grab a friend (or two), a glass of wine (or two), and enjoy a relaxing night of live music, delicious food, and great company. 🍷🎵✨ |
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 🎸 Spend your evening at Timber Hill Winery with Live Music featuring Richardson Acoustic! Kick back, sip your favorite wine, and enjoy an acoustic performance in the vineyard setting. Whether you're catching up with friends, enjoying date night, or simply unwinding after a long day, it's the perfect way to spend the evening. Great wine, tasty food, and live music—we'll see you there! 🍷🎶 |
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Calling all teachers! Before the school year kicks off, we’re throwing a Back to School Bash just for you! Here’s what’s in store: The first 50 teachers through the door will receive a limited-edition school bus or pencil box filled with fun surprises! Teachers can redeem up to TWO coupons (from the passports redeemed at the beginning of summer) in a single transaction—valid only on this day. Enjoy a fun teacher-themed photo opportunity to capture your back-to-school spirit! Can’t make… |
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 Join us for Yoga in the Vineyard! Whether you're a seasoned yogi or a first-timer, we encourage everyone to join us! Grab your mat and enjoy beautiful vineyard views paired with a relaxing yoga session hosted by Elise. ✨🧘♀️🍇 Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your choice. To receive a full refund, please notify our Events Manager at least 14 days in advance by emailing events@timberhillwinery.com. Tickets canceled within 14 days of… |
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 📺✨ Friends Trivia Night at Timber Hill Winery! How well do you really know Ross, Rachel, Monica, Chandler, Joey, and Phoebe? Join us from 6:00 PM–7:00 PM for a fun-filled evening of Friends-themed trivia, laughs, and friendly competition. Gather your team, grab a glass of wine, and put your knowledge of the iconic sitcom to the test—all while supporting a great cause. 💛 All proceeds benefit the Milton Junction Cemetery Association, helping preserve and care for our local community. Could… |
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Family Pet Photos in the Vineyard 🐾📸 Capture special memories with your family and furry friends while supporting a great cause! 50% of all ticket proceeds will directly benefit Be My Furever Dog Rescue and their mission of helping dogs find loving homes. We're excited to partner with Sam from SJ Film & Photo, who will be capturing your family's special moments in the vineyard. Your ticket includes: 📸 Two professionally edited photos by SJ Film & Photo 🐶 A…
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 🎶 Join us at Timber Hill Winery for Live Music featuring Two for the River! Enjoy an evening of great wine, good food, and live music that sets the perfect laid-back vibe. Grab your friends, find your favorite spot, and settle in for a night of easy listening and great company in the vineyard. 🍷✨🎸 |
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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.