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.
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 […]
Kick off the holiday season in style! Join us on December 1st from 12pm-2pm for a scrumptious brunch and unforgettable photos with Santa himself! Below are ticket options. Grab yours today! 
Admission Options (All tickets include access to our all you can eat brunch buffet): $25 for Adults – Includes one photo […]
Dive into a world of decadence and delight with us this holiday season! Join us as we embark on an unforgettable truffle and wine pairing experience – a celebration of flavors that promises to tantalize your taste buds and elevate your festive spirit. Imagine indulging in the rich, earthy notes of exquisite truffles perfectly […]
Unleash your inner Pumpkin King and put your "The Nightmare Before Christmas" knowledge to the ultimate test! Join us this Friday from 6:00pm-7:00pm for an evening of spine-tingling trivia that will transport you straight to Halloween Town. Whether you're a devoted Jack Skellington fan or an aficionado of all things Tim Burton, this is […]
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 […]
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 […]
Get ready to groove with us on December 8th from 2:00pm-4:00pm for an unforgettable afternoon of live music with the incredibly talented Jenna Lynne! 
Let her soulful tunes and captivating voice transport you to a world of musical magic. Whether you're a long-time fan or new to her sound, this is an experience […]
Unleash your inner artist and dive headfirst into the holiday spirit at our enchanting Wreath Workshop with Geske's Garden! Join us on December 10th from 5:00pm-7:00pm to discover the joy of crafting your very own wreath, just in time to dazzle your door and wow your guests this festive season. Whether you're a DIY veteran […]
Calling all book lovers! 
We're thrilled to invite you to our monthly Book Club, where we embark on exciting literary journeys and share our passion for reading. Whether you're a seasoned bookworm or just starting to explore the magic of books, our club is the perfect place to connect with fellow readers and […]
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 […]
Join us at Timber Hill Winery for our second Holiday Hunt Market! We will be bringing new and old items back to this unique vendorless market lets you browse an array of carefully curated Holiday gifts. From jewelry and dog gifts to baked goods and other festive surprises—all available for a quick and easy checkout […]
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 […]
Join us at Timber Hill Winery for our second Holiday Hunt Market! We will be bringing new and old items back to this unique vendorless market lets you browse an array of carefully curated Holiday gifts. From jewelry and dog gifts to baked goods and other festive surprises—all available for a quick and easy checkout […]
Get ready for an unforgettable afternoon filled with live music and good vibes! Join us on December 15th from 2:00pm-4:00pm as we welcome the incredibly talented Dan Brusky to our stage. Whether you're a die-hard music lover or just looking for a fun way to spend your afternoon, this is the perfect event for […]
This holiday season, escape into a realm of decadence and delight with us! We're thrilled to invite you to our second unforgettable truffle and wine pairing experience – a celebration of flavors that promises to tantalize your taste buds and elevate your festive spirit. Picture yourself indulging in the rich, earthy notes of exquisite […]
'Tis the season to get cheesy and create something truly special! Join us on December 17th from 5:00pm-7:00pm for an unforgettable Holiday Charcuterie Class. We're transforming your favorite meats, cheeses, and more into stunning Christmas tree boards that will wow your guests and elevate your festive gatherings. Whether you're a charcuterie connoisseur or just […]
Uncork the mysteries of the universe with us at Timber Hill Winery! 
We are thrilled to welcome back the extraordinary Psychic Readings by Brandi! Ready to explore the unknown and glimpse into your future? Join us and mark your calendars for this magical experience. 
Sign up at 2:45pm sharp as it's […]
Calling all Christmas enthusiasts! Are you ready to test your holiday knowledge and spread some festive cheer? 
Join us on December 20th from 6pm-7pm for an evening filled with laughter, fun, and a dash of friendly competition at our Christmas Trivia Night! 
Dust off those ugly sweaters and rally your friends, because […]
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 […]
Step into a winter wonderland like no other this December 21st, as we unravel the chilling mystery of "Murder at the North Pole"! Get ready to sleigh the night away with intrigue, suspense, and festive fun. Imagine the jingle of bells mixed with the whispers of secrets, as you and your friends become […]
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 […]
Get ready for an unforgettable afternoon of music and wine! Join us on December 22nd from 2:00pm to 4:00pm as we welcome the incredibly talented John Gay to our stage. Let his soulful melodies and captivating tunes transport you to a world of relaxation and joy, all while sipping on your favorite wines. Whether […]
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 […]
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 […]
Calling all Disney fans and trivia lovers! Join us for a magical evening of Disney Trivia on January 3rd from 6:00pm-7:00pm! 
Dive into the world of classic tales, unforgettable songs, and magical moments as you test your knowledge of all things Disney.Whether you’re a fan of princesses, villains, or adventures in far-off lands, […]
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.
