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 Dan Brusky

Name: Live Music with Dan Brusky
Start: 2025-04-05T18:00:00-05:00
End: 2025-04-05T20:00:00-05:00
Location: Timber Hill Winery

Join us for an evening of live music with the incredibly talented Dan Brusky! From heartfelt melodies to soulful tunes, his music will set the perfect vibe for a relaxing day at the winery. Sip on your favorite wines, unwind with friends, and let the music carry you away. Whether you’re here for the wine, the atmosphere, or just to enjoy some great live music, it’s the perfect way to spend your afternoon. Come grab a glass, find a cozy spot, and enjoy the sounds of Dan Brusky with us! 🍷🎶

Calendar

S	M	T	W	T	F	S
1 event 1 1 event, 1 2:00 pm - 4:00 pm Live Music with Jenna Lynne February 1 @ 2:00 pm - 4:00 pm Live Music with Jenna Lynne Join us for a fun-filled afternoon of live music with Jenna Lynne! 🎶🍷Grab your friends and head out to Timber Hill Winery as Jenna brings the tunes and sets the vibe for a relaxing, music-filled afternoon. Sip your favorite wines, enjoy great company, and soak in the sounds of live music at the winery.	1 event 2 1 event, 2 5:00 pm - 7:00 pm Lash Tutorial with Emily Anne Artistry February 2 @ 5:00 pm - 7:00 pm Lash Tutorial with Emily Anne Artistry Join us as we bring Emily of Emily Anne Artistry straight to you for an exclusive lash class! Emily will guide you through a variety of lash techniques, helping you build confidence and master the art of lashes. Whether you’re just starting out or looking to refine your skills, this class is designed to educate and inspire. 🎟 Tickets include all supplies needed 🍷 Food and drinks available for purchase separately Come ready to learn, practice, and elevate your lash…	1 event 3 1 event, 3 5:00 pm Recurring Traditional Bingo with Project 16:49 Lip Sync February 3 @ 5:00 pm Recurring Traditional Bingo with Project 16:49 Lip Sync 🎉 Join us for a Traditional Bingo Night benefiting Project 16:49 Lip Sync Fundraising! Bingo rounds are $5 each, starting at 5:00 PM. Cash is encouraged! Each round’s pot will be split between the winner and Project 16:49, so every game played supports a great cause. And that’s not all! 🎟️ We’ll also have a 50/50 raffle, giving you even more chances to win while supporting Project 16:49. Grab a drink, bring your lucky charm, and make your Tuesday night…	0 events 4 0 events, 4	0 events 5 0 events, 5	1 event 6 1 event, 6 6:00 pm - 7:00 pm Recurring Wineo Bingo with Echo February 6 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Echo Join us for a fun and feel-good night of Wineo Bingo with Echo! 🍷🎉 Sip on your favorite Timber Hill wines while playing rounds of Wineo Bingo, where all donations to play go directly toward supporting Echo’s mission of helping others in our community. Gather your friends, grab your bingo cards, and get ready for plenty of laughs, friendly competition, and exciting prizes. When your card fills up, don’t be shy—shout WINEO and claim your ultimate prize! It’s the perfect night…	1 event 7 1 event, 7 11:00 am - 4:00 pm Galentines Sip and Shop February 7 @ 11:00 am - 4:00 pm Galentines Sip and Shop 🚨💖 Galentine’s Sip & Shop 💖🚨 Celebrate Galentine’s Day in style with a day of shopping, sipping, and fun in Milton, WI! 🎉 Grab your gals and join us on February 7th for a special afternoon featuring exclusive deals, great company, and stress-free transportation starting at Timber Hill Winery! 🍷🛍️ 🎟️ Tickets: $25/person (Includes bus transportation and a special passport full of one-day-only deals!) 🛍️ Passport of Deals: Your ticket includes a passport packed with exclusive discounts and specials valid…
2 events 8 2 events, 8 10:30 am - 1:00 pm Bouquets & Brunch February 8 @ 10:30 am - 1:00 pm Bouquets & Brunch Bouquets & Brunch: A Galentine’s Day Celebration 💐💖 Grab your besties (or your favorite date!) and join us at Timber Hill Winery for the ultimate Valentine’s-inspired girls’ day out. Sip, snack, and create something beautiful together while celebrating love, friendship, and a little self-care. 💐 Build-A-Bouquet$25 per person — includes all flowers and supplies to design your own stunning bouquet to take home (or gift to someone special). 🥂 Brunch & DrinksSold separately — reserve your brunch spot here:https://timberhillwinery.com/sunday-brunch-buffet/ Whether…, 2:00 pm - 4:00 pm Live Music with Dan Brusky February 8 @ 2:00 pm - 4:00 pm Live Music with Dan Brusky Join us at Timber Hill Winery for an afternoon of live music with Dan Brusky. Sit back with a glass of your favorite wine, enjoy the relaxed winery atmosphere, and soak in the sounds. It’s the perfect way to spend your afternoon with friends or family. 🎶🍷	0 events 9 0 events, 9	1 event 10 1 event, 10 5:00 pm - 6:30 pm Sip, Dip & Graze: Fondue Night February 10 @ 5:00 pm - 6:30 pm Sip, Dip & Graze: Fondue Night 💖 Galentine’s Grazing & Fondue Night! 💖Join us for a fun and delicious evening! Our talented staff will craft a beautiful grazing table stocked with all your favorite bites, and you’ll get to graze to your heart’s content. Then, take your picks to the self-serve fondue station and enjoy dipping them in your choice of savory or sweet fondues.Your ticket includes:Access to the grazing tableAccess to the self-serve fondue stationDrinks are sold separately.It’s the perfect way to celebrate friendship, laughter,…	1 event 11 1 event, 11 5:00 pm - 7:00 pm Galentine’s Build-A-Bouquet Workshop February 11 @ 5:00 pm - 7:00 pm Galentine’s Build-A-Bouquet Workshop Join us for our Galentine’s Build-A-Bouquet Workshop! 💐Grab your Galentines (or your Valentine!) and get ready to create the perfect bouquet. All supplies are included—just show up ready to sip, socialize, and get creative! Food and drinks will be available for purchase separately. 💕🍷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.…	1 event 12 1 event, 12 6:00 pm - 7:00 pm Book Club February 12 @ 6:00 pm - 7:00 pm Book Club February Book: Remain by Nicholas Sparks and M. Night Shyamalan Join us for our February Book Club as we dive into the wonders of Remain by Nicholas Sparks and M. Night Shyamalan. Whether you’re just getting back into reading or a seasoned reader, everyone is welcome! 📚🍷	1 event 13 1 event, 13 6:00 pm - 7:00 pm Rom Com Trivia February 13 @ 6:00 pm - 7:00 pm Rom Com Trivia 💖 Rom-Com Trivia Night! 💖 Think you know everything about your favorite rom-coms? It’s time to put that knowledge to the test! Join us for an evening full of laughs, love, and trivia — all for a great cause. This event is donation-based to play and is a fundraiser benefiting the Timber Hill Lip Sync Team, raising funds for Project 16:49. In addition to trivia, enjoy extra fun activities like raffles and more, giving you even more chances to win…	0 events 14 0 events, 14
1 event 15 1 event, 15 2:00 pm - 4:00 pm Live Music with Idledaze February 15 @ 2:00 pm - 4:00 pm Live Music with Idledaze 🎶 Live Music at Timber Hill Winery! 🎶 Join us as Idledaze takes the stage for an unforgettable evening of music! Grab a drink, bring your friends, and kick back as Idledaze fills Timber Hill with amazing tunes. 🍷✨ Whether you’re here to sing along, or simply relax and enjoy the vibes, it’s the perfect way to spend an evening with great music and even better company. Don’t miss out on a night of fun, laughter, and unforgettable tunes!	1 event 16 1 event, 16 5:00 pm - 7:00 pm Sourdough Workshop February 16 @ 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…	0 events 17 0 events, 17	0 events 18 0 events, 18	1 event 19 1 event, 19 7:30 pm - 9:00 pm Comedy February 19 @ 7:30 pm - 9:00 pm Comedy 😂 Comedy Night at Timber Hill Winery! 😂 Get ready to laugh until your cheeks hurt! Grab your friends, your tickets, and a glass of wine, and join us for an evening full of hilarious jokes, witty banter, and good vibes. 🍷✨ Whether you’re here to chuckle, giggle, or roar with laughter, this is the perfect way to unwind and enjoy a night out. Don’t miss the fun—it’s going to be a comedy night to remember! Comedy Night seating is…	0 events 20 0 events, 20	1 event 21 1 event, 21 6:00 pm - 9:00 pm 70s Murder Mystery February 21 @ 6:00 pm - 9:00 pm 70s Murder Mystery 🎸🕺 Get ready for a groovy night! 🕺🎸Join us for the ’70s Murder Mystery! Step back in time to the decade of disco, bell bottoms, and big hair… but beware—there’s a twist. Can you uncover who the murderer is before it’s too late? 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 will be served…
1 event 22 1 event, 22 2:00 pm - 4:00 pm Live Music with Nathan Crawford February 22 @ 2:00 pm - 4:00 pm Live Music with Nathan Crawford 🎶 Live Music with Nathan Crawford! 🍷Spend a relaxing afternoon at Timber Hill Winery enjoying the soulful tunes of Nathan Crawford. Sip on your favorite wines, soak up the good vibes, and share the experience with friends and fellow music lovers. It’s the perfect way to unwind and enjoy great company, great music, and even better wine!	0 events 23 0 events, 23	1 event 24 1 event, 24 5:00 pm - 7:00 pm Paint and Sip February 24 @ 5:00 pm - 7:00 pm Paint and Sip 💕🎨 Join us for our February Paint & Sip! Annie from Vannie Gogh will guide you step-by-step as you create your very own wintery masterpiece—no experience needed, just come ready to sip, paint, and have fun! 🍷❄️ Grab a glass of wine, relax, and enjoy a creative night out with friends (or a date!). 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…	0 events 25 0 events, 25	0 events 26 0 events, 26	1 event 27 1 event, 27 6:00 pm - 7:00 pm Disney Trivia February 27 @ 6:00 pm - 7:00 pm Disney Trivia ✨ Disney Trivia at Timber Hill Winery! ✨ Get ready to relive the magic and test your knowledge of all things Disney! But that’s not all—the best part? You can play while supporting West Side AVID and helping students reach their goals. Entry is donation-based, and we’ll have raffles, games, and other fun ways to give back. Come for the nostalgia, stay for the fun, and leave knowing you made a difference!	0 events 28 0 events, 28