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.
We are excited to welcome Steadily Improv’ing to Milton for the very first time!
You’ll be treated to a night full of laughs!
This improv comedy show is all about being spontaneous and making it up as you go along. If you’re a fan of “Whose Line is it Anyways”, you do NOT want to miss this!
Join us at Timber Hill Winery for an afternoon filled with great tunes, delicious wine, and good vibes! 
We’re thrilled to welcome Idledaze to our stage for a live performance that’s sure to make your weekend unforgettable! 
Whether you’re a longtime fan or hearing them for the first time, their soulful sound and smooth melodies will have you tapping your toes and swaying with a glass of wine in hand. 
Get ready for a decadent experience where rich, handcrafted fudge meets the perfect pour. We've partnered with the experts at Skelly’s to create an unforgettable tasting event that brings out the best in both sweets and sips. Each pairing has been thoughtfully selected to highlight the unique flavors of both the fudge and the wine, making this a treat for your taste buds and a night to remember. Whether you're a wine lover, a fudge fanatic, or just looking for…
Get ready for a night of throwback fun and lyric-loving laughs at Finish The Lyrics Trivia Night! We’ll be traveling through the decades — from disco hits and 80s anthems to 90s jams and today’s top tunes — testing how well you really know the words to your favorite songs. Lyrics will be displayed on the screen… but it’s up to you to finish the line! No music, no hints — just your memory and your team’s brainpower.
Brunch Grazing Herd Social Join us on Sunday, July 6th from 11 AM to 1 PM for a delicious and relaxing brunch grazing experience! Mingle with fellow Herd members while enjoying a curated brunch grazing table, wine , and great company. 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 to secure a spot for your plus-ones.…
Join us on Sunday, July 6th from 2:00 PM to 4:00 PM for a relaxing afternoon of live music with Matt Jaye at Timber Hill Winery! Sip your favorite wine and take in the beautiful overlook of the vineyard while enjoying some smooth, summery tunes. It’s the perfect way to unwind and soak up the season! 
Tag your winery buddies and make it a Saturday to remember! #LiveMusic #MattJaye #TimberHillWinery #WineryVibes #SummerTunes #WisconsinWineries
Join us on Tuesday, July 8th from 5:30 PM to 6:30 PM for a peaceful and energizing Yoga in the Vineyard session with Elise! She'll guide you through every step—whether you're a seasoned yogi or trying it out for the first time, this class is for everyone. Enjoy the fresh air, vineyard views, and a moment of calm to recharge your week. 
Grab your tickets today and we’ll see you on the mat! #YogaInTheVineyard #TimberHillWinery #WellnessAndWine #SunsetYoga…
Join Us for July Book Club!This month we’re reading Happy Land by Dolen Perkins-Valdez. Whether you’re a regular or it’s your very first time, we’d love to see you there! To make it easier for everyone to join in the fun, we’re now offering two separate dates for book club. Choose the one that works best for you and come ready for great conversation, community, and wine!
Wineo Bingo with the Isaac Strong Foundation!Enjoy an evening of fun and fundraising with an hour of bingo, wine, and a 50/50 raffle! All donations to play go directly to the Isaac Strong Foundation, supporting a meaningful cause in our community. Sip, play, and make a difference—one bingo card at a time!
Join us on July 12th from 6:00pm to 8:00pm for live music with Back2Back at Timber Hill Winery . Enjoy an evening filled with great tunes , delicious wine , and good company . It’s the perfect way to unwind and make lasting memories — bring your friends and settle in for a fantastic night!
Join Us for a Sunday to Remember! We're combining wine, food, and baseball for the ultimate Sunday Funday—and you’re invited! 
Here’s the game plan: 
10:30 AM – 12:00 PM Kick off the day with a delicious brunch at Timber Hill Winery. Sip, savor, and fuel up before the big game! 
12:00 PM Hop on our bus departing from the winery—no need to worry about parking or traffic. 
12:30 PM Arrive at ABC Supply Stadium with time to…
Looking for the perfect way to spend your afternoon? Join us at Timber Hill Winery for a relaxing and fun-filled day featuring live music by the talented Jenna Lynne! She’ll be performing from 2:00 PM to 4:00 PM, bringing her beautiful vocals and heartfelt performance to our cozy winery setting. Whether you're sipping your favorite glass of wine, enjoying a flight with friends, or just soaking in the atmosphere, Jenna’s music will make the experience unforgettable.
Get ready to rewind the clock for a totally tubular night of 80s Trivia! 
We're partnering with the Milton Junction Cemetery Association for an evening packed with throwback fun, nostalgic vibes, and brain-teasing questions about the raddest decade ever. 
All donations to play go directly toward supporting the Cemetery Association’s efforts. So grab your friends, dust off your leg warmers, and join us for a gnarly good time—all for a great cause! 
Join us at Timber Hill Winery on Saturday, July 19th from 6:00 PM to 8:00 PM for an unforgettable evening of live music with the incredibly talented Trevor O’Connor! Whether you're a longtime fan or hearing him for the first time, Trevor’s smooth vocals and acoustic style are the perfect soundtrack to a relaxing summer night. Gather your friends, bring your appetite for wine and good vibes, and make a night of it with us. It’s the perfect way to unwind…
Mimosa & Brunch Pairing 
Start your Sunday off right with a delicious mimosa and brunch pairing at Timber Hill Winery! 
Enjoy a curated selection of bites perfectly paired with refreshing mimosas in a cozy, relaxing setting. On the menu: Smoked Salmon Crostini Mini Chicken & Waffles Cucumber Sandwiches French Toast Bake Fruit Tarts Tickets are limited — grab yours today and treat yourself to a brunch experience you won’t forget! 
get your tickets here
Join us on Sunday, July 20th from 2:00 PM to 4:00 PM for a relaxing afternoon of live music with Richardson Acoustic! Soak in the beautiful vineyard views while enjoying soulful tunes, a glass of wine in hand, and the perfect weekend vibes. No reservations needed—just bring your friends, grab your favorite wine, and let the music sway you!
Paint & Sip with Vannie Gogh! Join us for a fun and relaxing evening of creativity and wine at Timber Hill Winery! On Tuesday, July 22nd from 5:00 PM to 7:00 PM, the talented Vannie Gogh will guide you step-by-step to create this vibrant beach-themed masterpiece. Whether you're a seasoned artist or picking up a brush for the first time, you'll leave with a beautiful painting and great memories.
get your tickets here
Join us on Sunday, July 27th from 2:00 PM to 4:00 PM for a relaxing afternoon of live music with Sweet n' Sour Duo at Timber Hill Winery. Their smooth vocals and thoughtful song selection create the perfect backdrop for sipping wine and enjoying a peaceful day in the vineyard. Take in the scenic views, gather with friends or loved ones, and let the music and wine help you unwind before the week ahead. Whether you're a longtime fan or…
Join us on Sunday, July 27th for an unforgettable night with Steadily Improv’ing — a live improv comedy show full of surprises and spontaneous fun! This talented troupe creates hilarious scenes and characters completely on the spot, using nothing but quick thinking and audience suggestions. Every performance is unique, so you never know what wild and funny moments will happen next! 
If you’re a fan of Whose Line Is It Anyway?, you’ll love the fast-paced, off-the-cuff humor…
Get ready for a fun, hands-on evening at the BYO (Build Your Own) Pizza Herd Social! Join Amanda as she walks you through each step of crafting your perfect pie — from stretching the dough to selecting your favorite toppings. Whether you’re a pizza pro or a first-timer, this workshop is designed for all skill levels. While your creation is cooking, enjoy our housemade garlic bread, fresh from the oven and packed with flavor! You’ll have the option to bake…
Unwind and recharge with a peaceful evening flow among the vines on Thursday, July 31st from 5:30 PM – 6:30 PM. Whether you're a seasoned yogi or it's your first time on the mat, we welcome you to join us for this relaxing outdoor experience. Bring your mat, a friend, and enjoy an hour of movement, breath, and beautiful vineyard views! get your tickets here
90s Movie Trivia Night! Get ready to rewind time and test your knowledge of the most iconic films from the 1990s! From rom-coms and thrillers to teen classics and animated hits, we’re covering all your favorite throwbacks.Grab your friends, your flannel, and your movie know-how — it’s time to see who really remembers the ‘90s!
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.
