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.

Gilmore Girls Trivia

Name: Gilmore Girls Trivia
Start: 2025-09-26T18:00:00-05:00
End: 2025-09-26T19:00:00-05:00
Location: Timber Hill Winery

☕✨ Calling all Gilmore Girls fans! It’s time to put your knowledge of Stars Hollow to the test at Gilmore Girls Trivia Night! Whether you know every line of Luke and Lorelai’s witty banter, remember Rory’s endless reading list, or can quote Kirk’s odd jobs by heart, this is your chance to shine.

We’ll be diving into all the cozy charm of the show—expect questions that cover everything from the town meetings to the Dragonfly Inn, plus plenty of fun nods to Mrs. Patty and her unforgettable stories.

Bring your fellow Gilmore lovers, grab a drink (coffee or wine—both Rory and Lorelai approved), and settle in for a night of laughs, competition, and a whole lot of nostalgia. Will your team be the ultimate Gilmore Girls champions of Stars Hollow?

Calendar

S	M	T	W	T	F	S
	1 event 1 1 event, 1 5:00 pm - 7:00 pm Kick Off to Summer Herd Social June 1 @ 5:00 pm - 7:00 pm Kick Off to Summer Herd Social ☀️ 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…	0 events 2 0 events, 2	0 events 3 0 events, 3	1 event 4 1 event, 4 5:30 pm - 6:30 pm Yoga in the Vineyard June 4 @ 5:30 pm - 6:30 pm Yoga in the Vineyard 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…	1 event 5 1 event, 5 6:00 pm - 7:00 pm Pub Trivia June 5 @ 6:00 pm - 7:00 pm Pub Trivia 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!	2 events 6 2 events, 6 11:00 am - 12:00 pm Recurring Behind the Vines June 6 @ 11:00 am - 12:00 pm Recurring 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…, 2:00 pm - 3:00 pm Behind the Vines June 6 @ 2:00 pm - 3:00 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…
1 event 7 1 event, 7 2:00 pm - 4:00 pm Live Music with Bree Morgan June 7 @ 2:00 pm - 4:00 pm Live Music with Bree Morgan 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.	0 events 8 0 events, 8	0 events 9 0 events, 9	1 event 10 1 event, 10 5:00 pm - 8:00 pm Girls Night Out June 10 @ 5:00 pm - 8:00 pm Girls Night Out 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! …	1 event 11 1 event, 11 6:00 pm - 7:00 pm Book Club June 11 @ 6:00 pm - 7:00 pm Book Club 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.	1 event 12 1 event, 12 6:00 pm - 7:00 pm Recurring Wineo Bingo with Mercy Hospice Program June 12 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Mercy Hospice Program Join us for a night of Wine-O Bingo with Mercy Hospice Program! 🍷🎉 Grab a glass of wine and get ready for a fun evening of bingo, laughter, and community—all while supporting a meaningful cause. Every donation to play will go directly to Mercy Hospice Program and the compassionate care and support they provide to patients and families in our community. Bring your friends, enjoy a few rounds of bingo, and help make a meaningful impact while having a great…	0 events 13 0 events, 13
1 event 14 1 event, 14 2:00 pm - 4:00 pm Live Music with Sweet n Sour Duo June 14 @ 2:00 pm - 4:00 pm Live Music with Sweet n Sour Duo 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…	1 event 15 1 event, 15 2026-06-15 Teacher Appreciation Week Teacher Appreciation Week June 15 @ 11:00 am - June 19 @ 9:00 pm Teacher Appreciation Week Calling all teachers! 🍎☀️ We’re kicking off summer with our Annual Teacher Appreciation Week at Timber Hill Winery! Teachers are invited to stop in and receive a special summer passport with purchase—filled with exclusive coupons and deals you can use all summer long. You spent the year shaping minds — now it’s time to relax, sip, and celebrate the start of summer with us. Gather your teacher friends and celebrate summer the right way at Timber Hill Winery!	2 events 16 2 events, 16 2026-06-15 Teacher Appreciation Week 5:00 pm - 7:00 pm Painted Wine Glasses Workshop June 16 @ 5:00 pm - 7:00 pm Painted Wine Glasses Workshop 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,…	2 events 17 2 events, 17 2026-06-15 Teacher Appreciation Week 5:00 pm - 7:00 pm Paint and Sip June 17 @ 5:00 pm - 7:00 pm Paint and Sip 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	1 event 18 1 event, 18 2026-06-15 Teacher Appreciation Week	2 events 19 2 events, 19 2026-06-15 Teacher Appreciation Week 6:00 pm - 7:00 pm Live Music Trivia Night June 19 @ 6:00 pm - 7:00 pm Live Music Trivia Night 🎶 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…	0 events 20 0 events, 20
1 event 21 1 event, 21 2:00 pm - 4:00 pm Live Music with Britton Rea and Sarah Krahn June 21 @ 2:00 pm - 4:00 pm Live Music with Britton Rea and Sarah Krahn 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.	1 event 22 1 event, 22 5:00 pm - 7:00 pm Moms Night Out June 22 @ 5:00 pm - 7:00 pm Moms Night Out 💐 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…	0 events 23 0 events, 23	1 event 24 1 event, 24 5:30 pm - 6:30 pm Yoga in the Vineyard June 24 @ 5:30 pm - 6:30 pm Yoga in the Vineyard 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…	1 event 25 1 event, 25 5:30 pm - 7:00 pm Purse Bingo June 25 @ 5:30 pm - 7:00 pm Purse Bingo Sold Out! 🎉 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!…	0 events 26 0 events, 26	0 events 27 0 events, 27
1 event 28 1 event, 28 2:00 pm - 4:00 pm Live Music with Idledaze June 28 @ 2:00 pm - 4:00 pm Live Music with Idledaze Join us for live music with Idledaze! 🎶🍷 Idledaze will be bringing their laid-back energy for the perfect afternoon vibe. Sit back, relax, and enjoy a great mix of live music while you sip on your favorite wines and soak in the atmosphere. Grab your friends, find your spot, and let Idledaze set the tone for a fun and relaxing day at the winery.	0 events 29 0 events, 29	1 event 30 1 event, 30 5:30 pm - 6:30 pm Cake Pop & Dirty Soda Pairing June 30 @ 5:30 pm - 6:30 pm Cake Pop & Dirty Soda Pairing Join us for a Cake Pop & Dirty Soda Pairing—where sweet treats meet fizzy fun! Indulge in this delicious lineup all paired with a refreshing dirty soda: Blueberry Lemon Cake Pop Cherry Chip Cake Pop Cookies & Cream Cake Pop Grab your friends and treat yourself to a unique pairing experience you won’t want to miss! 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…