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.

Christmas Trivia and Ugly Sweaters with MAYC

Name: Christmas Trivia and Ugly Sweaters with MAYC
Start: 2026-12-18T18:00:00-06:00
End: 2026-12-18T19:00:00-06:00
Location: Timber Hill Winery

Get ready for a little holiday fun with Christmas Trivia and Ugly Sweaters at Timber Hill Winery, in partnership with the Milton Area Youth Center (MAYC)! 🎄🍷

Put on your most outrageous, festive, or downright ugly Christmas sweater and gather your friends for a fun evening of holiday-themed trivia! Test your Christmas knowledge, enjoy some friendly competition, and celebrate the season with us.

All donations to participate will go directly to the Milton Area Youth Center, helping support their programs and opportunities for local youth.

Whether you’re in it for the trivia, the ugly sweaters, or the holiday cheer, we’d love to see you there!

Calendar

S	M	T	W	T	F	S
1 event 1 1 event, 1 2:00 pm - 4:00 pm Live Music with Richardson Acoustic November 1 @ 2:00 pm - 4:00 pm Live Music with Richardson Acoustic 🎶 Live Music at Timber Hill Winery! Join us for live music with Richardson Acoustic! Grab a friend, pour yourself a glass of wine, and enjoy an afternoon of great music at Timber Hill Winery. 🍷 We’ll see you there!	0 events 2 0 events, 2	0 events 3 0 events, 3	0 events 4 0 events, 4	1 event 5 1 event, 5 5:30 pm - 7:00 pm Purse Bingo November 5 @ 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 you are unable to attend,…	1 event 6 1 event, 6 6:00 pm - 7:00 pm 80s Trivia with Friends of Library November 6 @ 6:00 pm - 7:00 pm 80s Trivia with Friends of Library 🎶 80s Trivia for a Cause! 🎶 Join us for 80s Trivia supporting Friends of the Library and all the amazing work they do in our community! 💜 Bring your team, test your 80s knowledge, and have a great time while supporting a wonderful local organization. All donations to play will directly benefit Friends of the Library! And that’s not all... they’ll also have raffles throughout the event, so you’ll have even more chances to win while giving back! 🎟️…	1 event 7 1 event, 7 11:00 am - 12:00 pm Behind the Vines November 7 @ 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 8 2 events, 8 10:30 am - 12:00 pm Bouquets and Brunch November 8 @ 10:30 am - 12:00 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: $25 per person — includes all your supplies and flowers. Your ticket also reserves your spot for brunch. Brunch & Drinks: Sold separately the day of the event. Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your choice.…, 2:00 pm - 4:00 pm Live Music with Jenna Lynne November 8 @ 2:00 pm - 4:00 pm Live Music with Jenna Lynne 🎶 Join us for live music with Jenna Lynne! Grab a seat, sip on your favorite wine, and enjoy the beautiful backdrop at Timber Hill Winery. 🍷 Bring a friend and settle in for an afternoon of great music, good wine, and even better company!	0 events 9 0 events, 9	0 events 10 0 events, 10	0 events 11 0 events, 11	1 event 12 1 event, 12 6:00 pm - 7:00 pm Book Club November 12 @ 6:00 pm - 7:00 pm Book Club 📚 November Book Club: Too Old for This by Samantha Downing Join us for our November Book Club as we dive into Too Old for This by Samantha Downing! Grab your copy, gather your fellow book lovers, and join us for an evening of good conversation, wine, and all things bookish. 🍷📖 Whether you’re a longtime book club member or joining us for the first time, we’d love to have you!	1 event 13 1 event, 13 6:00 pm - 7:00 pm Recurring Wineo Bingo with Badger State Therapy Dog Association November 13 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Badger State Therapy Dog Association 🐾🍷 Wineo Bingo with Badger State Therapy Dog Association! 🍷🐾 Join us for a fun night of Wineo Bingo while supporting the incredible work of the Badger State Therapy Dog Association! Enjoy your favorite Timber Hill wine, test your luck with Wineo Bingo, and help support an organization dedicated to bringing comfort, connection, and companionship through certified therapy dog teams throughout Southern Wisconsin. 🎟️ Donations to play will directly benefit the Badger State Therapy Dog Association! Grab your friends, enjoy…	1 event 14 1 event, 14 6:00 pm - 8:00 pm Home for the Holiday’s Murder Mystery November 14 @ 6:00 pm - 8:00 pm Home for the Holiday’s Murder Mystery Join us for Home for the Holidays: A Murder Mystery! It’s the most wonderful time of the year—until someone ends up dead. Gather your friends, pour a glass of wine, and help us uncover who murdered who in this festive night full of twists, laughter, and a little holiday mischief! Tickets are priced at $55 per person and include the murder mystery game, and dinner. Wine and beer will be available for purchase. This event is for adults only, 21 years and older. Dinner…
1 event 15 1 event, 15 2:00 pm - 4:00 pm Live Music with Tracy Jane Comer November 15 @ 2:00 pm - 4:00 pm Live Music with Tracy Jane Comer 🎶 Live Music with Tracy Jane Comer! 🎶 Join us for live music with Tracy Jane Comer! Grab a friend, enjoy a glass of wine, and settle in for an afternoon of great music at Timber Hill Winery. 🍷🎶	0 events 16 0 events, 16	1 event 17 1 event, 17 5:00 pm - 7:00 pm Paint and Sip November 17 @ 5:00 pm - 7:00 pm Paint and Sip Join us for a fall Paint & Sip! 🍂🎨 Annie will guide you step by step as you create your own masterpiece. Enjoy a fun, creative experience while sipping your favorite Timber Hill wines! Ticket Policy: If you’re unable to attend, your ticket may be transferred to a guest of your choice. For a full refund, please notify our Events Manager at least 14 days in advance by emailing events@timberhillwinery.com. Tickets canceled less than 14 days before the event are non-refundable. get…	0 events 18 0 events, 18	1 event 19 1 event, 19 7:30 pm - 9:00 pm Comedy Night November 19 @ 7:30 pm - 9:00 pm Comedy Night 😂 Comedy Night is back! Join us for our first Comedy Night of the season! Gather your friends, grab a glass of wine, and get ready for a night of laughs at Timber Hill Winery. 🍷 Come enjoy great comedy, good wine, and a fun night out! 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.com so we can get you seated together! Disclaimer:…	1 event 20 1 event, 20 6:00 pm - 7:00 pm New Girl Trivia November 20 @ 6:00 pm - 7:00 pm New Girl Trivia Join us for New Girl Trivia!🍷 Put your knowledge of Jess, Nick, Schmidt, Cece, Winston, and all the loft antics to the test! Grab your friends, form a team, and join us for a fun night of New Girl trivia at Timber Hill Winery. Come ready to laugh, reminisce, and see who knows the loft best!	0 events 21 0 events, 21
2 events 22 2 events, 22 12:00 pm - 4:00 pm Fall Sip and Shop November 22 @ 12:00 pm - 4:00 pm Fall Sip and Shop 🍂 Fall Sip & Shop Bus Trip 🛍️ Grab your friends and join us for a fun-filled afternoon of shopping, sipping, and supporting local businesses! 🍁 Join us on November 22nd for our Fall Sip & Shop Bus Trip, starting at Timber Hill Winery in Milton, WI. Enjoy an afternoon exploring local shops, discovering unique finds, and taking advantage of exclusive deals along the way. With convenient bus transportation and a special shopping passport included with your ticket, you can sit back,…, 2:00 pm - 4:00 pm Live Music with Back2Back Trio November 22 @ 2:00 pm - 4:00 pm Live Music with Back2Back Trio Join us for Live Music with Back2Back Trio! 🎶🍷 Spend your afternoon at Timber Hill Winery with great music, delicious wine, and good company. Back2Back Trio will be bringing the tunes, so grab your friends, find a seat, and settle in for a relaxing afternoon at the winery. Enjoy a glass of your favorite wine, grab a bite to eat, and let the music set the mood. We’ll see you at Timber Hill! 🍷🎶	1 event 23 1 event, 23 5:00 pm - 7:00 pm Wreath Workshop November 23 @ 5:00 pm - 7:00 pm Wreath Workshop 🎄 Join us for a festive Wreath Workshop! Get into the holiday spirit and enjoy an evening of creativity as you design your very own wreath to take home! Whether you love a classic look or want to add your own personal touch, you'll have plenty of options to make it uniquely yours. Each ticket includes a wreath and a variety of decorative crafting supplies to bring your creation to life. Just bring your creativity, and we'll take care of…	0 events 24 0 events, 24	0 events 25 0 events, 25	0 events 26 0 events, 26	0 events 27 0 events, 27	1 event 28 1 event, 28 2026-11-28 Small Business Saturday Small Business Saturday November 28 Small Business Saturday Small Business Saturday at Timber Hill Winery We’re kicking off Small Business Saturday in style — and you’re invited to celebrate with us! Tailgate Party: 9:00am–11:00amStart your morning off right in our parking lot with: DJ spinning great tunes Mimosas, Bloody Marys & more Tasty breakfast bites Fun, lively community vibes Doors Open at 11:00am Be among the first 50 shoppers through the door to snag one of our jam-packed goodie bags filled with treats from local businesses! Special Offers All Day 10% OFF your…
1 event 29 1 event, 29 2:00 pm - 4:00 pm Live Music with Steve Weber November 29 @ 2:00 pm - 4:00 pm Live Music with Steve Weber Join us for live music with Steve Weber! 🎶 Grab a glass of wine, get comfortable, and enjoy an afternoon of live acoustic music. Steve brings a fun mix making for the perfect soundtrack to your time at Timber Hill. Bring a friend, grab a seat, and spend the afternoon with us! 🍷	1 event 30 1 event, 30 5:00 pm - 7:00 pm Sourdough Workshop November 30 @ 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 is perfect for…