☀️ Kick Off to Summer Herd Social ☀️ Summer starts here! Join us for an evening packed with great food, lawn games, and all the summer vibes at Timber Hill Winery. We’re firing up the grill for an all-you-can-eat cookout experience featuring delicious summer favorites and plenty of fun along the way. Challenge your friends to cornhole, enjoy a variety of other lawn games, and soak in a night designed to celebrate the start of summer the right way. This…

Join us for Yoga in the Vineyard! 🌿🧘‍♀️ All are encouraged to join—whether you’re a first-time yogi or a seasoned pro, we’d love to see you out here. Come unwind, stretch, and soak in the peaceful vineyard views with us! 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…

Join us for Pub Trivia Night! 🍷✨ Put your knowledge to the test while enjoying a glass of your favorite wine. Grab your friends, form a team, and get ready for a fun night of friendly competition, laughs, and great pours!

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…

Join us for live music with Bree Morgan! 🎶🍷 Bree will be taking the stage at Timber Hill Winery, setting the perfect vibe as you sip on your favorite wines and enjoy a relaxing, music-filled afternoon.

 Save the Date!  Grab your friends and mark your calendars for a fun and meaningful night out!  Join us for Girls’ Night Out benefiting Triple H Ranch & Therapeutic Horsemanship  Wednesday, June 10, 2026 5–8 PM Timber Hill Winery – Milton, WI Enjoy a relaxing evening featuring: Drink specials Basket & 50/50 raffles A great cause supporting therapeutic horsemanship Best of all — it’s a FREE event! Let’s come together for laughter, friendship, and giving back. Tag your girls and make it a night to remember! …

June Book Club: Lady Tremaine by Rachel Hochhauser Join us for Book Club! 📚✨ All are welcome and encouraged to join us as we dive into Lady Tremaine by Rachel Hochhauser. Whether you’ve finished the book or are just getting started, come enjoy great conversation, good company, and a welcoming atmosphere.

Join us for live music with Sweet n Sour Duo! 🎶🍷 Sweet n Sour Duo will be taking the stage at Timber Hill Winery, bringing their unique blend of sound and energy for a performance you won’t want to miss. Sit back, relax, and enjoy the atmosphere as they set the perfect tone for an afternoon of great wine, good company, and live music. Grab a glass of your favorite Timber Hill wine, settle in, and let the music carry…

Join us at Timber Hill Winery as we team up with Craft & Vine for a fun and creative evening where you’ll hand-paint your own set of wine glasses! 🍷✨ They will guide you step-by-step through the featured design, making it easy and enjoyable for all skill levels. Prefer something more personal? You’re welcome to bring your own inspiration and choose your own colors to make your glasses uniquely yours. All supplies are included, and while they don’t use stencils,…

Join us for June’s Paint & Sip as Annie from Vannie Gogh guides you step-by-step through creating your very own masterpiece! 🎨✨Enjoy a relaxed, creative afternoon where you can sip your favorite wine, unwind, and bring this vibrant butterfly-and-flower scene to life. No experience needed—just come ready to have fun and leave with a painting you’ll be proud of! get your tickets here

🎶 Live Music Trivia Night with Jenna Lynne! 🎤 Get ready for a fun night of music and friendly competition as Jenna Lynne plays 15–20 second clips of iconic 2000s hits. Your challenge? Work with your team to name that tune! 🎵 Think you’ve got what it takes to take home the win? 🏆 Beyond the music, this night is about making a difference 💙 All proceeds support the West Side Women Empowerment Club, helping fund meaningful community impact. Your…

Join us for live music with Britton Rea and Sarah Krahn! 🎶🍷 Britton Rea and Sarah Krahn will be taking the stage at Timber Hill Winery, bringing an engaging mix of live music to set the perfect backdrop for your afternoon. Enjoy their performance as you sip on your favorite wines, relax with friends, and take in the welcoming atmosphere. It’s the perfect way to spend a laid-back day filled with great music, great wine, and even better company.

💐 Calling all Moms! Join us for a Moms Night Out as we get together and celebrate you! We’re inviting moms of all ages to enjoy a night of great food, drinks, and fun. No tickets required — just come ready to sip, relax, and enjoy a night out! 🍷✨ 💬 Get to Know Each Other: We’ll have fun icebreaker questions and activities to help you connect, share some laughs, and make new friends! ✨ Bonus Treat: Permanent jewelry will…