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

Name: Live Music with Trevor O’Connor
Start: 2025-07-19T18:00:00-05:00
End: 2025-07-19T20:00:00-05:00
Location: Timber Hill Winery

Join us at Timber Hill Winery on Saturday, July 19th from 6:00 PM to 8:00 PM for an unforgettable evening of live music with the incredibly talented Trevor O’Connor! Whether you’re a longtime fan or hearing him for the first time, Trevor’s smooth vocals and acoustic style are the perfect soundtrack to a relaxing summer night. Gather your friends, bring your appetite for wine and good vibes, and make a night of it with us. It’s the perfect way to unwind and enjoy local talent in a beautiful setting! 🍷🎸✨

Calendar

S	M	T	W	T	F	S
						1 event 1 1 event, 1 11:00 am - 12:00 pm Behind the Vines August 1 @ 11:00 am - 12:00 pm Behind the Vines 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…
2 events 2 2 events, 2 11:00 am - 4:00 pm Thriftfest Midwest August 2 @ 11:00 am - 4:00 pm Thriftfest Midwest 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.…, 2:00 pm - 4:00 pm Live Music with Trevor O’connor August 2 @ 2:00 pm - 4:00 pm Live Music with Trevor O’connor 🎶 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!	0 events 3 0 events, 3	1 event 4 1 event, 4 5:30 pm - 6:30 pm Build Your Own Ice Cream Sundae Herd Social August 4 @ 5:30 pm - 6:30 pm Build Your Own Ice Cream Sundae Herd Social 🍨 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…	0 events 5 0 events, 5	1 event 6 1 event, 6 5:30 pm - 7:00 pm Purse Bingo August 6 @ 5:30 pm - 7:00 pm Purse Bingo 🎉 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 7 1 event, 7 6:00 pm - 7:00 pm Recurring Wineo Bingo with the Humane Society of Southern Wisconsin August 7 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with the Humane Society of Southern Wisconsin 🍷 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! 🐶🐱🎉	0 events 8 0 events, 8
1 event 9 1 event, 9 2:00 pm - 4:00 pm Live Music with Matt Jaye August 9 @ 2:00 pm - 4:00 pm Live Music with Matt Jaye 🎵 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.	0 events 10 0 events, 10	0 events 11 0 events, 11	0 events 12 0 events, 12	0 events 13 0 events, 13	1 event 14 1 event, 14 6:00 pm - 7:00 pm Pub Trivia August 14 @ 6:00 pm - 7:00 pm Pub Trivia 🧠🍷 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!	1 event 15 1 event, 15 12:00 pm - 4:00 pm Annual Carnival August 15 @ 12:00 pm - 4:00 pm Annual Carnival 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…
0 events 16 0 events, 16	0 events 17 0 events, 17	0 events 18 0 events, 18	1 event 19 1 event, 19 5:00 pm - 7:00 pm Meat Raffle with Milton Junction Cemetery Association August 19 @ 5:00 pm - 7:00 pm Meat Raffle with Milton Junction Cemetery Association 🥩🎉 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!	1 event 20 1 event, 20 6:00 pm - 7:00 pm Book Club August 20 @ 6:00 pm - 7:00 pm Book Club 📖 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…	0 events 21 0 events, 21	1 event 22 1 event, 22 6:00 pm - 8:00 pm Live Music with Duane Worden August 22 @ 6:00 pm - 8:00 pm Live Music with Duane Worden 🎶 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. 🍷🎵✨
1 event 23 1 event, 23 2:00 pm - 4:00 pm Live Music with Richardson Acoustic August 23 @ 2:00 pm - 4:00 pm Live Music with Richardson Acoustic 🎸 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! 🍷🎶	1 event 24 1 event, 24 2026-08-24 Back to School Bash Back to School Bash August 24 Back to School Bash 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…	0 events 25 0 events, 25	1 event 26 1 event, 26 5:00 pm - 7:00 pm Paint and Sip August 26 @ 5:00 pm - 7:00 pm Paint and Sip Join us for our Paint & Sip! 🎨🍷🌻 Create a stunning sunflower inspired by the swirling beauty of Starry Night with step-by-step instruction from Annie of Vannie Gogh! Whether you're an experienced artist or picking up a paintbrush for the first time, you'll enjoy a fun and relaxing evening filled with creativity, great company, and your favorite Timber Hill wines. Bring your friends, sip, paint, and leave with a beautiful masterpiece that's perfect for brightening your home or giving as a gift.…	1 event 27 1 event, 27 5:30 pm - 6:30 pm Yoga in the Vineyard August 27 @ 5:30 pm - 6:30 pm Yoga in the Vineyard 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…	1 event 28 1 event, 28 6:00 pm - 7:00 pm Friends Trivia August 28 @ 6:00 pm - 7:00 pm Friends Trivia 📺✨ 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. 💛	0 events 29 0 events, 29
2 events 30 2 events, 30 12:00 pm - 4:00 pm Family Pet Photos in the Vineyard August 30 @ 12:00 pm - 4:00 pm Family Pet Photos in the Vineyard 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…, 2:00 pm - 4:00 pm Live Music with Two for the River August 30 @ 2:00 pm - 4:00 pm Live Music with Two for the River 🎶 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. 🍷✨🎸	0 events 31 0 events, 31