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.
We are excited to welcome Steadily Improv’ing to Milton for the very first time!
You’ll be treated to a night full of laughs!
This improv comedy show is all about being spontaneous and making it up as you go along. If you’re a fan of “Whose Line is it Anyways”, you do NOT want to miss this!
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Join us on Sunday, July 27th from 2:00 PM to 4:00 PM for a relaxing afternoon of live music with Sweet n' Sour Duo at Timber Hill Winery. Their smooth vocals and thoughtful song selection create the perfect backdrop for sipping wine and enjoying a peaceful day in the vineyard. Take in the scenic views, gather with friends or loved ones, and let the music and wine help you unwind before the week ahead. Whether you're a longtime fan or…
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🎭 Join us on Sunday, July 27th for an unforgettable night with Steadily Improv’ing — a live improv comedy show full of surprises and spontaneous fun! ✨ This talented troupe creates hilarious scenes and characters completely on the spot, using nothing but quick thinking and audience suggestions. Every performance is unique, so you never know what wild and funny moments will happen next! 😂 If you’re a fan of Whose Line Is It Anyway?, you’ll love the fast-paced, off-the-cuff humor… |
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Get ready for a fun, hands-on evening at the BYO (Build Your Own) Pizza Herd Social! Join Amanda as she walks you through each step of crafting your perfect pie — from stretching the dough to selecting your favorite toppings. Whether you’re a pizza pro or a first-timer, this workshop is designed for all skill levels. While your creation is cooking, enjoy our housemade garlic bread, fresh from the oven and packed with flavor! You’ll have the option to bake… |
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Unwind and recharge with a peaceful evening flow among the vines on Thursday, July 31st from 5:30 PM – 6:30 PM. Whether you're a seasoned yogi or it's your first time on the mat, we welcome you to join us for this relaxing outdoor experience. 🌿🍇🍷 Bring your mat, a friend, and enjoy an hour of movement, breath, and beautiful vineyard views! get your tickets here |
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🎬 90s Movie Trivia Night! 🎬Get ready to rewind time and test your knowledge of the most iconic films from the 1990s! From rom-coms and thrillers to teen classics and animated hits, we’re covering all your favorite throwbacks.Grab your friends, your flannel, and your movie know-how — it’s time to see who really remembers the ‘90s! |
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🎶Join us on Sunday, August 3rd from 2:00 PM to 4:00 PM for an afternoon of incredible live music with the talented Bree Morgan! Sip your favorite wine and soak in the sounds of this powerhouse performer—it’s the perfect Sunday vibe! 🍷🎤 |
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🎉 Majority Rules Game Night – Benefiting Rock County Cancer Coalition 🎗️ Join us for a fun-filled Tuesday evening of laughter, great wine, and supporting a great cause! We’re partnering with the incredible Rock County Cancer Coalition to bring you Majority Rules – a hilarious twist on traditional trivia. It’s simple, silly, and super interactive! We’ll ask a series of questions, your team will turn in answers after each round, and the majority answer wins the points – no need… |
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🧘♀️ Yoga in the Vineyard 🍇 Join us for a peaceful evening of Yoga in the Vineyard on Thursday, August 7th from 5:30 PM to 6:30 PM. Breathe in the fresh vineyard air, soak up the beautiful views, and enjoy a relaxing flow led by a certified instructor. Whether you're a beginner or a seasoned yogi, this is the perfect way to unwind midweek. Don't forget your mat—wine and good vibes await! get your tickets here |
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Get ready for a paw-some night of sips, smiles, and bingo! 🎉 Join us for Wineo Bingo as we team up with the amazing folks at the Humane Society of Southern Wisconsin 🐶🐱 to raise money for animals in need! Grab your lucky charm 🍀 and a glass of your favorite Timber Hill wine 🍇 and settle in for a few exciting rounds of bingo 🎱. There will be fabulous prizes, lots of laughs, and best of all—ALL donations to… |
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Join us on Saturday, August 9th from 6:00 PM – 8:00 PM for an unforgettable evening of live music with the incredibly talented Mattea Joy! 🎸🎵 Sip on your favorite Timber Hill wine 🍷, relax on the patio 🍇, and soak in the soulful sounds and good vibes as the sun sets 🌅. Whether you're winding down the week or kicking off the weekend, this is the perfect way to enjoy great tunes, great wine, and even better company! |
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Timber Hill Summer Market – Sunday Morning Fun! Join us for our very own Timber Hill Summer Market — your one-stop shop for delicious, fresh-baked goods, beautiful flower bouquets and unique market finds! From sweet treats to fun surprises, we’re bringing the bakery vibes and more to your Sunday morning. Bring your friends, sip some wine, and stroll through our cozy market!
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Wind down your weekend with us on Sunday, August 10th from 2:00 PM – 4:00 PM as we welcome the talented Tracy Jane Comer to the winery stage! 🎹🎵 Enjoy a relaxing afternoon filled with smooth tunes, great wine 🍷, and the cozy vibes of Timber Hill Winery 🍇✨. Tracy’s soulful voice and acoustic charm make for the perfect Sunday soundtrack—whether you're sipping with friends, enjoying a date, or just treating yourself to some peaceful patio time 🌞🪑. |
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Join us for a Rock Rebounding Class with Carrie on Monday, August 11th from 5:30 PM – 6:10 PM! For just $30, enjoy a fun, energizing rebounding workout led step-by-step by Carrie. After you sweat it out, treat yourself to a glass of your favorite Timber Hill wine to wrap up the evening on a high note! Spaces are limited – reserve yours today! get your tickets here |
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📚Join us this August as we dive into Heartwood by Amity Gaige—a beautifully written novel about resilience, roots, and rediscovery. Whether you’ve read it before or this is your first time, we’d love for you to be part of the conversation! To make it easier for everyone to join in the fun, we’re now offering two separate dates for book club. Choose the one that works best for you and come ready for great conversation, community, and wine! |
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🛋️☕ Join us on Friday, August 15th for the ULTIMATE Friends Trivia Night with the Milton Junction Cemetery Association! 🎉 Think you know everything about Ross’s divorces, Joey’s acting career, Monica’s obsessive cleaning, or Chandler’s job (does anyone know what he does)? Now’s your chance to prove it! Enjoy a night filled with laughs, great company, and all the nostalgia from your favorite '90s sitcom. 🙌 💸 We’ll also have raffles and a 50/50 drawing to keep the excitement going… |
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🕓 Registration closes on July 31st—don’t wait! 🎨👕 Herd Tie Dye T-Shirt Event Join us for a colorful and creative night at the winery! Tie dye your very own official Timber Hill T-shirt 👚—each one comes printed with “Herd Member” on the back to show off your winery pride! Sip on wine 🍷, enjoy great company 🥂, and create a wearable masterpiece. We’ll provide everything you need, including the T-shirt, dyes, and all supplies—just bring your creativity and get ready for a vibrant time!… |
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Join us Tuesday, August 19th from 5:30 PM to 6:30 PM for Yoga in the Vineyard. Breathe in the fresh air, stretch out among the vines, and unwind with a gentle yoga session surrounded by nature’s beauty. Perfect for all levels—whether you’re a seasoned yogi or just starting out. 🌞🍃 Bring your mat, your calm, and let the peaceful vineyard setting help you recharge your body and mind. Namaste. 🙏✨ get your tickets here |
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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 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!… |
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🎶✨ Saturday nights are for great wine and even better music! ✨🎶 Join us on Saturday, August 23rd from 6:00 PM to 8:00 PM for Live Music with Duane Worden! 🎤🍷 Kick back and enjoy an evening of smooth tunes, good vibes, and your favorite Timber Hill wines. Whether you're dancing under the sunset or just relaxing with friends, Duane's performance is sure to make your Saturday night unforgettable. 🌅🎸 Come for the wine, stay for the music! 🎶🍇🪩 |
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🎶 Sunday Funday just got sweeter! 🎶 Join us on Sunday from 2:00 PM to 4:00 PM for Live Music with the talented Cyndi Meyer! 🎤🍷 Relax with a glass of your favorite wine, soak in the vineyard vibes, and enjoy Cyndi’s soulful vocals and acoustic melodies. Whether you're singing along or just sipping and swaying, it's the perfect way to spend a Sunday afternoon! ☀️🎸 Bring your friends, grab a seat, and let the music move you! 💃🪑✨ |
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Join us on Wednesday, August 27th from 5:00 PM – 7:00 PM for a summer-inspired Paint and Sip! Annie will walk you through each step as you create your own cheerful watermelon picnic masterpiece — complete with curious little ants! 🐜🍉 No experience needed — just bring your creativity and get ready for a fun evening of painting, sipping, and laughter! Limited spots available — grab your ticket today! 🎟️🖌️ get your tickets here |
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🔮✨ Join us Thursday, August 28th from 4:00 PM to 7:00 PM as we welcome the incredible Brandi for an unforgettable afternoon of Tarot Readings! 🌌 For just $25, embark on a magical journey of self-discovery and uncover the mysteries the universe has in store for you. ✨ 💫 Readings start promptly at 4:00 PM and are first come, first serve—so arrive early, grab a glass of wine, and get ready to uncork your future with insights that could change… |
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🎶 Disney Tunes Trivia Night! 🎶 Get ready for a magical evening of music, memories, and giving back! We’ll play clips from your favorite Disney categories—and it’s up to YOU to name that song! ✨ The winning team will walk away with an epic prize, but the real magic is in the mission: All proceeds go to support the Shining Star Grant Program, helping Milton-area families in need when disaster strikes—whether from fire, flooding, or other extreme circumstances. 🎟️ Entry… |
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Join us on August 30th from 11:00am-2:00pm where Hallie will be live painting the vineyars during the event—an exciting opportunity to watch her create one of her vivid, expressive pieces in real time. Known for her lively, colorful style and bold brushwork, Hallie captures the energy and emotion of the moment in each stroke. In addition to the live painting experience, guests will be able to browse and shop a curated selection of prints from Hallie’s past work. Whether you're… |
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🎶✨ Make your Sunday afternoon special! Join us Sunday, August 31st from 2:00 PM to 4:00 PM for Live Music with Britton and Sarah! 🎤🍷 Relax, sip your favorite wine, and enjoy the warm harmonies and great vibes these talented musicians bring to our cozy winery setting. Perfect for a laid-back afternoon with friends and good music! 🌞🎸 Grab a seat, bring your friends, and let the music carry you through a beautiful Sunday! 🎶🍇💫 |
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Back to School Brunch Grazing 🍽️🍾 Calling all Moms! 💕 After a busy summer, it’s time to treat yourself with a well-earned morning out. Join us for a relaxing Back to School Brunch featuring a beautifully curated brunch grazing table filled with all your favorite bites! 🧀🥐🍓 🥂 Mimosas, your favorite wines, and more will be available for purchase to help toast the new school year. Not a mom? No worries—everyone is welcome to enjoy this fun and flavorful event!… |
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Get ready to sip, dab, and win—all while making a difference! Every dollar spent on bingo cards 🎟️ goes directly to benefit Special Olympics and the incredible athletes they support. 💙 ✨ Enjoy a lively evening of wine, laughter, and great prizes, knowing your participation is helping empower individuals with intellectual disabilities through sports and community. 🙌 📅 Mark your calendars – don’t miss out on this feel-good event for a fantastic cause! Let’s raise a glass and raise some… |
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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.
