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.
Get your friends together and join us for our Cinco de Mayo Fiesta! On May 5th from 4-7pm we will have a taco bar, fun games, and Margarita specials! We also will have 2 new Slushie flavors to celebrate. Purchase your tickets with the link below so you don’t miss out on all of the fun! 1 ticket will get you all-you-can-eat tacos!
Join us for an unforgettable afternoon of live music with the incredibly talented Bree Morgan on April 27th from 2:00 PM to 4:00 PM! 
Relax, sip on your favorite Timber Hill wine, and enjoy the perfect soundtrack to your weekend. Whether you're here for the music, the wine, or the great company, it's going to be a memorable afternoon. Don't miss out on the fun – we can't wait to see you there! 
#LiveMusic #BreeMorgan #TimberHillWinery #WineAndMusic
April Paint & Sip with Vannie Gogh! 
Join us for April’s Paint & Sip with the talented Annie from Vannie Gogh! This month, Annie will guide you through the magic of painting a beautiful umbrella, symbolizing April showers. 
Secure your spot and let your creativity flow! 
Join us for Wineo Bingo at Timber Hill Winery, benefiting Project 16:49! Bring a donation of any amount to play and enjoy an hour of bingo from 6:00 PM to 7:00 PM . Play for fun prizes while supporting a great cause that helps local youth in need . Don’t miss out on this exciting and meaningful evening—see you there!
Join us for our Second Annual Bine to Vine 5K, Derby Style! 
Dress up in your best Derby style with your furry friend and race for a great cause! This fun 5k run/walk (or 1-mile walk option) takes you from Good Works to Timber Hill Winery, benefiting the Humane Society of Southern Wisconsin. 
Best Costume Contest: The most fabulous dog-and-human duo will be crowned the winner and take home an amazing prize! 
Registration: 10:00 AM 
Race…
Join us at Timber Hill Winery for the annual Kentucky Derby Hat Contest! Show off your creativity and don your most extravagant hat for a chance to win an exciting prize! Everyone is welcome to participate, so grab your friends, family, and fellow Derby enthusiasts for an unforgettable celebration. Whether you go for classic elegance, whimsical flair, or bold and over-the-top designs, we can’t wait to see your Derby style! Judging begins at 3:00 PM sharp! Be sure to arrive early to…
Calling all dog moms! Join us on May 4th from 11:00 AM – 1:00 PM as we celebrate YOU—the ones who do it all! We’re teaming up with Brown Paws Dog Rescue for a pawsome event featuring: Caricatures Dog Mom Market Dog Treats for Sale Permanent Jewelry (Get matching charms with your pup!) Raffles And more! Come shop, snag some new bling, enter in some raffles, and help support rescue dogs! Tag your fellow dog moms and let’s make this a tail-wagging good time! #DogMomDay #ShopForAPaws #TimberHillWinery
Kick back, relax, and enjoy live music with Sweet n Sour Duo at Timber Hill Winery! Join us on May 4th from 2:00 PM – 4:00 PM for an afternoon of great tunes, delicious wine, and good vibes. Grab a glass, find a cozy spot, and let the music set the mood. See you there! #LiveMusic #TimberHillWinery #SweetNSourDuo
Calling all Herd members! Get ready to celebrate Cinco de Mayo in style at our Herd Social Fiesta! Indulge in delicious drinks, a mouthwatering taco bar, and experience our space transformed into the ultimate fiesta party! Don’t miss out on the fun—mark your calendars and join us for a night to remember! #HerdSocialFiesta #CincoDeMayo #TacoBarDelight #WineAndFun #PartyTime #JoinTheHerd #TimberHillWinery This event is exclusively available to Herd members, but members are welcome to bring guests along to join in the fun! Guests will need their own tickets, so don’t forget…
Celebrate spring and the special moms in your life with a fun and floral evening at Timber Hill Winery! During this hands-on workshop, you'll get to build your very own custom bouquet using a beautiful variety of fresh flowers. Whether you're creating a gift for Mother’s Day or treating yourself to some blooms, our team will be there to guide you every step of the way. Enjoy a glass of wine as you arrange your bouquet, sip and socialize, and…
Join us for our monthly Book Club at Timber Hill Winery! This May, we’re reading The In-Between Bookstore by Edward Underhill. Grab a glass of wine, dive into a great book, and enjoy a fun discussion with fellow book lovers! Whether you’ve read the book cover to cover or just want to listen in, we’d love to have you. 
Tag a friend and let’s talk books! #TimberHillBookClub #WineAndBooks **This event will take place in The Loft. If…
Test your music knowledge at our Live Music Trivia Night with Jenna Lynne! She’ll play 15-20 seconds of iconic 90s and 2000s hits, and it’s up to you and your team to guess the song. Think you have what it takes? 
Not only will the winning team score the ultimate prize, but this night is also for a great cause! 
All proceeds support the AVID program, helping students achieve their dreams. Donations grant you entry, plus…
Live Music with Jenna Lynne! Join us at Timber Hill Winery on May 10th from 6:00 PM – 8:00 PM for an evening of fantastic live music with Jenna Lynne! Grab a glass of your favorite wine, sit back, and enjoy her incredible performance in a cozy winery atmosphere. Tag your friends and make it a night to remember! 
#LiveMusic #TimberHillWinery #JennaLynne #WineAndMusic
Mother’s Day Brunch Treat the amazing moms in your life to a relaxing and delicious day out at Timber Hill Winery! This Mother’s Day, we’re rolling out a brunch buffet full of sweet and savory favorites – and of course, plenty of wine to sip and enjoy! 
Menu Includes:
Scrambled Eggs, Bacon, Sausage
Waffles with all the fixings
Breakfast Potatoes
Biscuits & Gravy
Fresh Fruit Bowl
Donut Holes, Pastries & Mini Muffins
Bruschetta
Taco Dip & Mac…
Make your Sunday afternoon extra special with live music at Timber Hill Winery! Join us on May 11th from 2:00 PM – 4:00 PM as Cyndi Meyer sets the perfect vibe with her amazing performance. Sip, relax, and soak in the music—because Sundays are made for good wine and great tunes! #SundayVibes #LiveMusic #TimberHillWinery #CyndiMeyer
Get your hands dirty & your wine glasses full! Join us on May 13th for an Herb & Veggie Planting Class with Geske Gardens! 
They'll walk you through the planting process, share tips for long-term care, and help you grow your green thumb—all while you sip on your favorite Timber Hill Wines! 
Spots are limited—reserve yours today! get your tickets here
Join us for Wineo Bingo at Timber Hill Winery, benefiting Project 16:49! Bring a donation of any amount to play and enjoy an hour of bingo from 6:00 PM to 7:00 PM . Play for fun prizes while supporting a great cause that helps local youth in need . Don’t miss out on this exciting and meaningful evening—see you there!
Join us for Wineo Bingo at Timber Hill Winery, benefiting Project 16:49! 
Bring a donation of any amount to play and enjoy an hour of bingo from 6:00 PM to 7:00 PM 
. Play for fun prizes while supporting a great cause that helps local youth in need 
. Don't miss out on this exciting and meaningful evening—see you there!
Join us on May 18th from 11:00 AM – 2:00 PM for a purr-fect afternoon filled with adorable kittens, wine, and giving back! 
We’re teaming up with HSSW to support kittens in need, and we’d love your help! 
How You Can Help:We encourage guests to bring monetary or in-kind donations to support these little furballs. Check out their wishlist here: https://www.petsgohome.org/ways-to-give/wish-list/ 
What to Expect: Meet adoptable kittens Enjoy wine & kitten snuggles
Learn about fostering & volunteering…
Kick back, sip, and enjoy live music with Steve Weber on Sunday, May 18th, from 2:00 PM to 4:00 PM! Gather your friends for an afternoon of great wine, good vibes, and fantastic tunes. It’s the perfect way to unwind and soak up the weekend! 
Save the date and join us! #LiveMusic #TimberHillWinery #SundayTunes
Attention, loftmates! It’s time to put your New Girl knowledge to the test! Join us for New Girl Trivia on May 23rd from 6:00 PM - 7:00 PM at Timber Hill Winery. 
Grab your trivia dream team (Cece and Winston approved) and get ready for a night of laughs, Schmidt-isms, and maybe even a little True American energy! 
Tag your fellow New Girl fans and let’s see who reigns supreme as the ultimate trivia champion! Will…
Join us for an unforgettable evening of Live Music with Tracy Jane Comer on Saturday, May 24th, from 6:00 PM to 8:00 PM! Let the soulful melodies and vibrant tunes set the perfect mood for a relaxing night at Timber Hill Winery. Whether you're sipping on your favorite wine or enjoying great company, this is the perfect way to unwind and enjoy the weekend. Don’t miss out on this special performance – it’s going to be a night…
Join us for a relaxing afternoon of Live Music with Sam Rodewald on Sunday, May 25th, from 2:00 PM to 4:00 PM! Enjoy the perfect blend of great tunes, delicious wine, and good company as we wind down the weekend together at Timber Hill Winery. Whether you're a regular or a first-time guest, it's the perfect way to spend a Sunday afternoon. Come for the music, stay for the vibes! #LiveMusic #TimberHillWinery #SundayFunday #WeekendVibes #WineAndMusic
Yoga in the Vineyard is back on May 27th from 5:30 PM to 6:30 PM! Join us for a peaceful evening surrounded by the beauty of the vineyard as Elise guides you through a relaxing and refreshing yoga session. Whether you’re a seasoned yogi or it’s your first time on the mat, everyone is welcome! Grab your tickets now and treat yourself to some well-deserved serenity! 
#YogaInTheVineyard #TimberHillWinery #SunsetStretch #WineAndUnwind get your tickets here
Join us on Thursday, May 29 at Timber Hill Winery in Milton for an evening of networking, fun, and laughter—all while supporting a great cause! This special event, hosted by Girls Night Out of Rock County, will help raise funds for Triple H Ranch, a local organization making a difference in our community. Free Admission 
Bring cash for delicious food and beverages, exciting raffle baskets, and a thrilling 50/50 drawing! Gather your friends and enjoy a fantastic night…
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.
