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.

Live Music with Nathan Crawford

Name: Live Music with Nathan Crawford
Start: 2026-02-22T14:00:00-06:00
End: 2026-02-22T16:00:00-06:00
Location: Timber Hill Winery

🎶 Live Music with Nathan Crawford! 🍷
Spend a relaxing afternoon at Timber Hill Winery enjoying the soulful tunes of Nathan Crawford. Sip on your favorite wines, soak up the good vibes, and share the experience with friends and fellow music lovers. It’s the perfect way to unwind and enjoy great company, great music, and even better wine!

Calendar

S	M	T	W	T	F	S
		0 events 1 0 events, 1	0 events 2 0 events, 2	0 events 3 0 events, 3	1 event 4 1 event, 4 6:00 pm - 7:00 pm Recurring Wineo Bingo with CASA September 4 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with CASA 🎉🍷 Wineo Bingo with CASA of Rock County! 🍷🎉 Join us for a night of Wineo Bingo with CASA of Rock County! All donations to play directly benefit CASA and their mission to advocate for children in need. Sip on your favorite Timber Hill wines, enjoy delicious food, and play for your chance to win fun prizes throughout the evening. There is no registration required—just bring your friends, make a donation, and get ready to yell "WINEO!"	2 events 5 2 events, 5 11:00 am - 12:00 pm Behind the Vines September 5 @ 11:00 am - 12:00 pm Behind the Vines Step behind the scenes and discover the story behind every sip. Behind the Vines is a customized, guided wine tasting designed to immerse you in the heart of Timber Hill Winery. Led by one of our knowledgeable wine guides, guests will be thoughtfully guided through four hand-selected wine samples, each chosen to highlight the diversity and character of our wines. Your tasting is paired with a curated charcuterie cone to perfectly complement the experience. Following the tasting, guests will enjoy…, 6:00 pm - 8:00 pm Live Music with Ken Curtis September 5 @ 6:00 pm - 8:00 pm Live Music with Ken Curtis Join us at Timber Hill Winery for an afternoon of live music with Ken Curtis! 🎶🍷 Ken will be taking the stage and filling the winery with great tunes, making it the perfect way to spend your evening. Grab a glass of your favorite Timber Hill wine, relax, and enjoy some live music with us!
1 event 6 1 event, 6 2:00 pm - 4:00 pm Live Music with Bill Conway September 6 @ 2:00 pm - 4:00 pm Live Music with Bill Conway 🎶 Live Music with Bill Conway! 🎶 Join us for an afternoon of live music with Bill Conway! From 2:00 PM–4:00 PM, Bill will take the stage and set the tune! 🎸🍷 And as Ethan would say… he’s SO good! 😉 Grab a glass of wine, relax, and enjoy some great live music with us! We’ll see you there! 🍇	0 events 7 0 events, 7	0 events 8 0 events, 8	0 events 9 0 events, 9	1 event 10 1 event, 10 6:00 pm - 7:00 pm Book Club September 10 @ 6:00 pm - 7:00 pm Book Club 📖 September Book: The Whistler by Ann Patchett 📚✨ Book Club at Timber Hill Winery – September Edition ✨📚 Join us this September for Book Club as we gather to discuss The Whistler by Ann Patchett! Whether you're an avid reader or just looking for a reason to pick up a great book, everyone is welcome. Our Book Club is a relaxed and welcoming space to unwind, connect with fellow book lovers, and enjoy engaging conversation—all while sipping your favorite…	1 event 11 1 event, 11 6:00 pm - 7:00 pm Pub Trivia September 11 @ 6:00 pm - 7:00 pm Pub Trivia Join us for Pub Trivia from 6:00pm–7:00pm! 🍻🧠 Grab your teammates, put your thinking caps on, and get ready to play! Bring your best trivia knowledge and see if your team can take home the win! 🏆 We’ll see you there! 🍷	1 event 12 1 event, 12 5:00 pm - 8:00 pm Annual Fish Boil September 12 @ 5:00 pm - 8:00 pm Annual Fish Boil 🐟 By popular demand, our Annual Fish Boil is back! We’re bringing the legendary Fitzgerald’s Genoa Junction on the road to Timber Hill Winery for a one-night-only experience you won’t forget! They don’t take their show on the road very often, so you won’t want to miss this rare treat. From 5:00 PM–8:00 PM, enjoy a traditional Wisconsin Fish Boil alongside delicious Honey BBQ Chicken while soaking in 🎶 live music from Top Flight and sipping your favorite Timber Hill…
1 event 13 1 event, 13 2:00 pm - 4:00 pm Live Music with Sweet n Sour Duo September 13 @ 2:00 pm - 4:00 pm Live Music with Sweet n Sour Duo 🎶 Live Music with Sweet n Sour Duo! 🎶 Join us for an afternoon of live music with the Sweet n Sour Duo! 🍷🎸 Sit back, relax, sip on your favorite Timber Hill wine, and enjoy some great tunes! Bring your friends, grab a glass, and make an afternoon of it! We can’t wait to see you! ❤️	0 events 14 0 events, 14	0 events 15 0 events, 15	0 events 16 0 events, 16	1 event 17 1 event, 17 5:00 pm - 8:00 pm Fields of Flavor September 17 @ 5:00 pm - 8:00 pm Fields of Flavor Join us for an unforgettable evening where food, wine and community come together to create a lasting impact. Fields of Flavor is more than a beautiful farm-to-table dinner. It is an opportunity to invest in brighter futures for youth experiencing homelessness. Set against the backdrop of a picturesque winery, guests will enjoy a thoughtfully curated multi-course meal featuring perfectly paired wines. Cocktail hour begins at 5:00 PM and dinner commences at 6:00 PM Every ticket purchased helps provide hope, stability,…	0 events 18 0 events, 18	0 events 19 0 events, 19
1 event 20 1 event, 20 2:00 pm - 4:00 pm Live Music with Dan Brusky September 20 @ 2:00 pm - 4:00 pm Live Music with Dan Brusky 🎶 Live Music with Dan Brusky! 🎶 Join us for an afternoon of live music with Dan Brusky! 🎸🍷 Grab your friends, sip on your favorite Timber Hill wine, and settle in for some great tunes! Whether you're stopping by for a glass or staying for the music, it's the perfect way to spend your day at the winery. ❤️	0 events 21 0 events, 21	0 events 22 0 events, 22	2 events 23 2 events, 23 4:00 pm - 7:00 pm Tarot Readings with Brandi September 23 @ 4:00 pm - 7:00 pm Tarot Readings with Brandi Join us for an afternoon of tarot readings with Brandi. Each private tarot reading is just $25 for a 10-12 minute session! First come first served, sign up begins at 3:45pm. Space is limited You must be there in person to get your name on the list. Sip on your favorite wines while gaining insights and guidance for the year ahead. Whether you’re curious about love, career, or your overall future, Brandi’s tarot readings offer a unique and enlightening experience. Don’t…, 4:00 pm - 7:00 pm Tarot Readings with Brandi September 23 @ 4:00 pm - 7:00 pm Tarot Readings with Brandi Join us for an afternoon of tarot readings with Brandi. Each private tarot reading is just $25 for a 10-12 minute session! First come first served, sign up begins at 3:45pm. Space is limited You must be there in person to get your name on the list. Sip on your favorite wines while gaining insights and guidance for the year ahead. Whether you’re curious about love, career, or your overall future, Brandi’s tarot readings offer a unique and enlightening experience. Don’t…	0 events 24 0 events, 24	1 event 25 1 event, 25 6:00 pm - 7:00 pm Gilmore Girls Trivia September 25 @ 6:00 pm - 7:00 pm Gilmore Girls Trivia Calling all Stars Hollow superfans! ☕💫 Join us for Gilmore Girls Trivia and put your knowledge of all things Lorelai, Rory, Luke, Emily, and the rest of the gang to the test! From unforgettable quotes and quirky Stars Hollow moments to relationships, drama, and all those coffee-fueled adventures—how well do you really know the Gilmore Girls? 👯 Grab your team ☕ Bring your Gilmore Girls knowledge 🏆 Compete for trivia glory 🍷 Enjoy some wine while you play! Whether you're…	0 events 26 0 events, 26
1 event 27 1 event, 27 10:30 am - 12:00 pm Bouquets & Brunch September 27 @ 10:30 am - 12:00 pm Bouquets & Brunch Bouquets & Brunch! Grab your besties and join us for the ultimate girls’ day out at Timber Hill Winery! Create your own beautiful bouquet and enjoy a delicious brunch with your favorite people. Build-A-Bouquet: $25 per person — includes all your supplies and flowers. Your ticket also reserves your spot for brunch. Brunch & Drinks: Sold separately the day of the event. Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your choice.…	1 event 28 1 event, 28 5:30 pm - 6:30 pm Create your Own Fall Cocktail Herd Social September 28 @ 5:30 pm - 6:30 pm Create your Own Fall Cocktail Herd Social 🍂 Create Your Own Fall Cocktail Herd Social! 🍷Calling all Herd members — it’s time to mix, shake, and sip! 🍸Join us for a hands-on evening where YOU become the mixologist!For just $20, you’ll receive 2 cocktail sheets to design up to two custom drinks of your very own creation.🍷 Pick your wine or liquor🍯 Choose your syrup✨ Add your favorite fun extrasOur staff will gather all your ingredients, and then it’s your turn to shake, stir, and sip your…	1 event 29 1 event, 29 5:00 pm - 7:00 pm Paint and Sip September 29 @ 5:00 pm - 7:00 pm Paint and Sip 👻 Ghouls Night Out: September Paint & Sip! 🍷🎨 Join us for a spooky and creative night out! Annie will guide you step-by-step as you paint your very own ghostly masterpiece while sipping on your Timber Hill favorites and enjoying great company. Grab your friends, pick your favorite wine, and get ready for a night of painting, sipping, and a little Halloween fun! 👻🍷 Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of…	1 event 30 1 event, 30 5:30 pm - 6:00 pm Cookie Cake Decorating September 30 @ 5:30 pm - 6:00 pm Cookie Cake Decorating 🍪 Cookie Cake Decorating Class 🌵 Join us at Timber Hill Winery for a fun and creative Cookie Cake Decorating Class! Whether you're a seasoned baker or have never picked up a piping bag before, this class is perfect for all skill levels. You'll learn how to prepare piping bags and create beautiful buttercream succulents in gorgeous shades of green and blue while decorating your own chocolate chip cookie cake. Our instructor will guide you step-by-step, making it easy and…