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

 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…

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…

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 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…

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…