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 ready to laugh until your sides ache! Join us for another unforgettable night of comedy from 7:30pm-8:30pm! 
Whether you're looking to shake off the stress of the day, or just want to enjoy some top-notch entertainment, our lineup of hilarious comedians will have you rolling in the aisles. It's the perfect way […]
Get ready for a night of fun, laughter, and giving back! Join us for Wineo Bingo, where every sip and every number called brings us one step closer to supporting an incredible cause – the Milton Area Youth Center. 
Imagine an evening filled with the clinking of glasses, the excitement of winning, and […]
Step back in time and sip in style at Speakeasy on The Hill! Join us every Saturday and Sunday as we shake up the weekend with the most exquisite craft cocktails in town. Whether you're a cocktail connoisseur or just looking for a unique way to unwind, our hidden gem promises an unforgettable experience. Our mixologists […]
Calling all music and wine lovers! Mark your calendars for an unforgettable afternoon on December 29th from 2pm to 4pm. We're thrilled to host the incredibly talented Sweet n' Sour duo for a live performance that promises to be the perfect blend of soulful melodies and vibrant tunes. Whether you're a fan of smooth […]
Unleash your inner artist and get into the holiday spirit with us! Join the fabulous Annie from Vannie Gogh for another unforgettable Paint and Sip event, where creativity meets relaxation! 
Whether you're a seasoned painter or picking up a brush for the first time, Annie's expert guidance will lead you through the magical […]
Ring in the New Year with us in style! 
Indulge in a delightful four-course food and wine pairing that will leave your taste buds dancing. Each course is carefully curated to bring you a perfect blend of flavors and wine pairings. From the first bite to the last sip, it’s a celebration […]
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.
