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.

Create your Own Holiday Cocktail Herd Social

🍷🎄✨ Herd Social: Holiday Cocktail & Mocktail Creation Party! ✨🍸Get into the holiday spirit with a festive night of creativity and cheer! For just $20, you’ll receive 📝 2 cocktail sheets to craft up to two custom holiday drinks — your choice of wine or liquor as the base! 🍷🥂🎅 Here’s how it works:👉 Choose your base (wine or liquor)👉 Mix in your favorite syrups, garnishes & add-ons👉 Our team gathers your ingredients👉 Then it’s your turn to shake, stir & sip your merry creation! 🎁✨This jolly event is exclusive to Herd members, but members are welcome to bring guests along to join in the fun! 🎄Guests will need their own tickets — so be sure to grab one for your plus-ones!Not a member yet? Join the Herd here:👉 https://timberhillwinery.com/herd-wine-club/

Calendar

S	M	T	W	T	F	S
				0 events 1 0 events, 1	1 event 2 1 event, 2 6:00 pm - 7:00 pm Stranger Things Trivia January 2 @ 6:00 pm - 7:00 pm Stranger Things Trivia Mark your calendars! 🗓️ Timber Hill Winery is turning upside down as we bring Stranger Things Trivia straight to you! Think you know Eleven, Mike, Dustin, and the rest of the gang better than anyone else? Come test your knowledge of Hawkins, the Upside Down, and all your favorite moments from the hit series. Bring your friends, grab a drink, and see who really rules the trivia world—Will it be you, or will the Demogorgon claim victory? Don’t miss out…	0 events 3 0 events, 3
1 event 4 1 event, 4 2:00 pm - 4:00 pm Live Music with Bill Conway January 4 @ 2:00 pm - 4:00 pm Live Music with Bill Conway Join us for an afternoon of live music with Bill Conway! 🎸 Settle in with your favorite glass of wine 🍷 and enjoy a relaxing set filled with great tunes and good company. It’s the perfect way to unwind and spend your Sunday at the winery!	1 event 5 1 event, 5 5:00 pm - 7:00 pm Sourdough Workshop January 5 @ 5:00 pm - 7:00 pm Sourdough Workshop ✨ Join us for a Sourdough Workshop! ✨ Margaret from Blue Bird Custom Creations will guide you step-by-step through everything you need to become a sourdough pro! Learn how to care for your starter, master the basics of sourdough baking, and leave ready to bake at home with everything included: 🍞 A live sourdough starter📖 Detailed instructions and tried-and-true recipes🥖 A ready-to-bake loaf of sourdough bread Whether you’re a beginner or just looking to improve your skills, this hands-on workshop…	0 events 6 0 events, 6	0 events 7 0 events, 7	1 event 8 1 event, 8 6:00 pm - 7:00 pm Book Club January 8 @ 6:00 pm - 7:00 pm Book Club Join us as we dive into We Solve Murders by Richard Osman! 📚✨ This witty and suspenseful read is full of twists, charm, and unforgettable characters. Grab a glass of wine, settle in, and get ready for a fun evening of great conversation and mystery!	1 event 9 1 event, 9 6:00 pm - 7:00 pm Recurring Wineo Bingo with KANDU January 9 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with KANDU 🎉 Join us for Wineo Bingo with KANDU! 🎉Sip, laugh, and play for a cause! 🍷🖤 All donations to play go directly to support KANDU and their mission to make a difference in the community. Come have fun, win prizes, and support a great non-profit at the same time! 🎁✨	0 events 10 0 events, 10
2 events 11 2 events, 11 10:30 am - 1:00 pm Bouquets and Brunch January 11 @ 10:30 am - 1:00 pm Bouquets and Brunch 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: $20 per person — includes all your supplies and flowers Brunch & Drinks: Sold separately — reserve your brunch spot here https://timberhillwinery.com/sunday-brunch-buffet/ It’s the perfect way to sip, snack, and get creative together! get your tickets here, 2:00 pm - 4:00 pm Live Music with Richardson Acoustic January 11 @ 2:00 pm - 4:00 pm Live Music with Richardson Acoustic 🎶 Join us for Live Music with Richardson Acoustic! 🎶Relax with your favorite glass of wine 🍷 and enjoy an afternoon filled with soothing acoustic tunes and good company. The perfect way to unwind at the winery! ✨	0 events 12 0 events, 12	1 event 13 1 event, 13 5:00 pm - 6:30 pm Winter Beach Bash Herd Social January 13 @ 5:00 pm - 6:30 pm Winter Beach Bash Herd Social Join us for our Winter Beach Bash Herd Social! Escape the cold and soak up the vibes as we transform Timber Hill into your very own beach in January! 🌴❄️ From bright summer décor to tropical tunes, we’re bringing the warmth straight to you. For just $15, you’ll enjoy a spread of delicious beach-themed bites and a fun, laid-back atmosphere perfect for shaking off those winter blues. Whether you come dressed in your best beachwear or just ready for a good…	0 events 14 0 events, 14	1 event 15 1 event, 15 4:00 pm - 7:00 pm Psychic Readings January 15 @ 4:00 pm - 7:00 pm Psychic Readings Discover what the future holds at Timber Hill Winery! Join us for an afternoon of psychic readings with Brandi. Each 15-minute reading is just $25! Sip on your favorite wines while gaining insights and guidance for the year ahead. Whether you’re curious about love, career, or your overall future, Brandi’s readings offer a unique and enlightening experience. Don’t miss this chance to explore what the future may have in store! #PsychicReadings #TimberHillWinery #WineAndWisdom About Brandi: An ethical, professional psychic clairvoyant, Brandi comes with over…	1 event 16 1 event, 16 6:00 pm - 7:00 pm Movie Quote Trivia January 16 @ 6:00 pm - 7:00 pm Movie Quote Trivia 🎬 Join us for the Ultimate Movie Quote Trivia! 🎬Think you know your movie quotes? We’ll give you the quote—it’s up to you to name the movie! Test your cinematic knowledge and have a blast competing with friends. 🐾 Supporting a Purr-fect Cause!We’re thrilled to partner with Misfit Felines, who are bringing raffles, a 50/50, and opportunities to support at-risk cats and reduce the homeless cat population. 🎁 Special Bonus: Bring in a food donation for Misfit Felines and be…	3 events 17 3 events, 17 11:00 am - 12:00 pm Recurring Behind the Vines: Guided Wine Tasting Herd Social January 17 @ 11:00 am - 12:00 pm Recurring Behind the Vines: Guided Wine Tasting Herd Social 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: Guided Wine Tasting Herd Social January 17 @ 2:00 pm - 3:00 pm Behind the Vines: Guided Wine Tasting Herd Social 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…, 6:00 pm - 9:00 pm Masquerade Murder Mystery January 17 @ 6:00 pm - 9:00 pm Masquerade Murder Mystery 🎭 Join us for the Masquerade Murder Mystery! 🕵️‍♀️Step into an evening of intrigue, suspense, and fun! Everyone is encouraged to bring their best masquerade look 🪡✨ to add to the mystery, but it’s not required. Come for the thrills, stay for the drama, and see if you can solve the case before the night is over! 🕯️🔍 Tickets are priced at $55 per person and include the murder mystery game, and dinner. Wine and beer will be available for…
1 event 18 1 event, 18 2:00 pm - 4:00 pm Live Music with Bryan Piper January 18 @ 2:00 pm - 4:00 pm Live Music with Bryan Piper Join us for an unforgettable afternoon of live music with Bryan Piper! Bring your friends and family and let the music take you away as we fill the air with great tunes, laughter, and good vibes. Enjoy a relaxing atmosphere, connect with fellow music lovers, and make memories that will last long after the last note plays.	1 event 19 1 event, 19 5:00 pm - 7:00 pm Build Your Own S’mores Bar January 19 @ 5:00 pm - 7:00 pm Build Your Own S’mores Bar Join us for a Build Your Own S’mores Bar at Timber Hill Winery! 🍫🔥 For just $15 per person, you’ll get everything you need to create up to four delicious, custom s’mores. Choose your favorite chocolates, marshmallows, and toppings, then toast your masterpiece and enjoy it right here at the winery. It’s a fun, cozy, and tasty add-on perfect for families, date nights, groups, or anyone looking to sweeten their visit. Come get creative, indulge your sweet tooth, and make…	0 events 20 0 events, 20	0 events 21 0 events, 21	1 event 22 1 event, 22 7:30 pm - 9:00 pm Comedy January 22 @ 7:30 pm - 9:00 pm Comedy Join us for our January Comedy Night! Get ready to laugh until your cheeks hurt and your sides ache. Bring your friends for an evening full of hilarious moments, unforgettable jokes, and non-stop fun. Don’t wait—grab your tickets before it’s too late! Comedy Night seating is assigned! If you’re planning to sit with someone whose ticket you purchased separately, please email our Events Manager at events@timberhillwinery.comso we can get you seated together! get your tickets here	0 events 23 0 events, 23	1 event 24 1 event, 24 6:00 pm - 8:00 pm Live Music with Ken Curtis January 24 @ 6:00 pm - 8:00 pm Live Music with Ken Curtis Kick back and enjoy an evening of live music with Ken Curtis! Grab your friends and family, tap your toes to the tunes, and let the good vibes take over. It’s the perfect way to relax, enjoy great music, and make lasting memories together.
1 event 25 1 event, 25 2:00 pm - 4:00 pm Live Music with Steve Weber January 25 @ 2:00 pm - 4:00 pm Live Music with Steve Weber 🎶 Join us for live music with Steve Weber! 🍷 Grab a drink, settle into your seat, and let the good vibes take over as he fills the winery with great tunes. It’s the perfect way to unwind and enjoy a cozy afternoon with friends! ✨	1 event 26 1 event, 26 5:00 pm - 7:00 pm Makeup Dump with Emily Anne Artistry January 26 @ 5:00 pm - 7:00 pm Makeup Dump with Emily Anne Artistry Join us for the ultimate Makeup Dump as we bring Emily of Emily Anne Artistry straight to you! Grab your brushes and makeup bag and come ready to learn. Emily will share tips and tricks to help you confidently create your own makeup looks. 🎟 Your ticket includes expert instruction and all the tips and tricks you need 💄 Makeup and brushes are not included Disclaimer: If you are unable to attend, your ticket may be transferred to a guest…	1 event 27 1 event, 27 5:00 pm - 7:00 pm Paint and Sip January 27 @ 5:00 pm - 7:00 pm Paint and Sip 🎨 Paint Your Heart Out 💖 Join us for Paint Your Heart Out, a fun and freeing paint & sip experience led by Annie from Vannie Gogh—no experience needed. We’ll start with a simple heart, then you’ll make it your own using bold colors and creative tools. Brush, dip, dot, mark, scratch, splatter, and drip as you turn your canvas into a one-of-a-kind expression of you. Sip, relax, and let go—there are no rules, just creativity. All supplies provided. Come…	0 events 28 0 events, 28	1 event 29 1 event, 29 4:00 pm - 7:00 pm The Skin Reset Event featuring HydraFacial January 29 @ 4:00 pm - 7:00 pm The Skin Reset Event featuring HydraFacial We are thrilled to welcome Bellasazi Salon & Spa to Timber Hill Winery as they bring the incredible HydraFacial experience to our space! We’re excited to partner with their talented team to host a special HydraFacial Launch Event, giving our guests the opportunity to experience this advanced, results-driven facial treatment in a relaxed, welcoming setting. HydraFacial is a medical-grade facial known for delivering immediate, visible results with no downtime and is suitable for all skin types. This exclusive launch event…	1 event 30 1 event, 30 6:00 pm - 7:00 pm Mean Girls Trivia January 30 @ 6:00 pm - 7:00 pm Mean Girls Trivia Join us for Mean Girls Trivia with the Milton Public Library! 💖📚 Grab your friends, form your team, and get ready to put your fetch knowledge to the test with questions all about everyone’s favorite iconic movie. Whether you know every quote by heart or just love a good trivia night, this event is for you! ✨ The best part? All donations to play will go directly toward supporting the Milton Public Library, so you can have fun while giving…	0 events 31 0 events, 31

December 28

December 28, 2025 @ 2:00 pm - 4:00 pm

Live Music with Brooke Nunn

December 29

December 30

December 30, 2025 @ 5:00 pm - 7:00 pm

Paint and Sip

There are no events on this day.

There are no events on this day.

January 2

January 2 @ 6:00 pm - 7:00 pm

Stranger Things Trivia

There are no events on this day.

January 4

January 4 @ 2:00 pm - 4:00 pm

Live Music with Bill Conway

January 5

January 5 @ 5:00 pm - 7:00 pm

Sourdough Workshop

There are no events on this day.

There are no events on this day.

January 8

January 8 @ 6:00 pm - 7:00 pm

Book Club

January 9

January 9 @ 6:00 pm - 7:00 pm

Wineo Bingo with KANDU

There are no events on this day.

January 11

January 11 @ 10:30 am - 1:00 pm

Bouquets and Brunch

January 11 @ 2:00 pm - 4:00 pm

Live Music with Richardson Acoustic

There are no events on this day.

January 13

January 13 @ 5:00 pm - 6:30 pm

Winter Beach Bash Herd Social

There are no events on this day.

January 15

January 15 @ 4:00 pm - 7:00 pm

Psychic Readings

January 16

January 16 @ 6:00 pm - 7:00 pm

Movie Quote Trivia

January 17

January 17 @ 11:00 am - 12:00 pm

Behind the Vines: Guided Wine Tasting Herd Social

January 17 @ 2:00 pm - 3:00 pm

Behind the Vines: Guided Wine Tasting Herd Social

January 17 @ 6:00 pm - 9:00 pm

Masquerade Murder Mystery

January 18

January 18 @ 2:00 pm - 4:00 pm

Live Music with Bryan Piper

January 19

January 19 @ 5:00 pm - 7:00 pm

Build Your Own S’mores Bar

There are no events on this day.

There are no events on this day.

January 22

January 22 @ 7:30 pm - 9:00 pm

Comedy

There are no events on this day.

January 24

January 24 @ 6:00 pm - 8:00 pm

Live Music with Ken Curtis

January 25

January 25 @ 2:00 pm - 4:00 pm

Live Music with Steve Weber

January 26

January 26 @ 5:00 pm - 7:00 pm

Makeup Dump with Emily Anne Artistry

January 27

January 27 @ 5:00 pm - 7:00 pm

Paint and Sip

There are no events on this day.

January 29

January 29 @ 4:00 pm - 7:00 pm

The Skin Reset Event featuring HydraFacial

January 30

January 30 @ 6:00 pm - 7:00 pm

Mean Girls Trivia

There are no events on this day.

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.