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.

Thriftfest Midwest

Name: Thriftfest Midwest
Start: 2026-08-02T11:00:00-05:00
End: 2026-08-02T16:00:00-05:00
Location: Timber Hill Winery

Join us for the ultimate curated secondhand shopping event!

Thriftfest Midwest is a curated vintage, secondhand, and handmade clothing market focusing on sustainability and artistic expression. Shop from the areas best secondhand clothing vendors from Vintage shops to handmade and upcycled accessories.

This is an event you do not want to miss! We will have activities, snacks, and over 20 clothing and accessories vendors. This event will be located on the vineyard of Timber Hill with the most stunning view. Timber Hill will also be offering their full drink and food menu!

Early bird will be from 11 to 12 pm and general admission from 12 to 4 pm.

We hope to see you!

Calendar

S	M	T	W	T	F	S
			0 events 1 0 events, 1	1 event 2 1 event, 2 5:30 pm - 6:30 pm Yoga in the Vineyard July 2 @ 5:30 pm - 6:30 pm Yoga in the Vineyard Join us for Yoga in the Vineyard! Whether you're a seasoned yogi or a first-timer, we encourage everyone to join us! Grab your mat and enjoy beautiful vineyard views paired with a relaxing yoga session hosted by Elise. ✨🧘‍♀️🍇 Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your choice. To receive a full refund, please notify our Events Manager at least 14 days in advance by emailing events@timberhillwinery.com. Tickets canceled within 14 days of…	1 event 3 1 event, 3 6:00 pm - 7:00 pm Greys Anatomy Trivia July 3 @ 6:00 pm - 7:00 pm Greys Anatomy Trivia Join us for Grey’s Anatomy Trivia Night! 🩺✨ We’re bringing the questions to put your knowledge to the test while supporting a great cause — the Milton Junction Cemetery Association. Enjoy a fun night of trivia, raffles, and plenty of Grey’s-inspired moments. Grab your team and join the fun!	0 events 4 0 events, 4
1 event 5 1 event, 5 2:00 pm - 4:00 pm Live Music with Duane Worden July 5 @ 2:00 pm - 4:00 pm Live Music with Duane Worden Join us for an evening of live music with Duane Worden! Enjoy great tunes, delicious wine, and beautiful vineyard views as you unwind with friends and family. Sit back, sip, and enjoy live music🎶🍷	0 events 6 0 events, 6	1 event 7 1 event, 7 3:00 pm - 7:00 pm Chunky Knit Blanket Workshop July 7 @ 3:00 pm - 7:00 pm Chunky Knit Blanket Workshop Join us for a fun evening making cozy blankets with great food and yummy drinks!! Chunky knit workshops are perfect for beginners or experienced knitters! We will be making blankets with just our hands. Everyone leaves with a cozy new blanket in a blanket bag and a new skill. After the workshop you also get emailed instructions and yarn buying tips for future projects. We make lap blankets that often end up full body blankets. I encourage you to choose…	0 events 8 0 events, 8	1 event 9 1 event, 9 6:00 pm - 7:00 pm Book Club July 9 @ 6:00 pm - 7:00 pm Book Club July Book: Yesteryear by Caro Claire Burke Join us for Book Club as we dive into Yesteryear by Caro Claire Burke! 📚✨Whether you’re just getting back into reading or you’ve been a lifelong book lover, everyone is welcome. Come enjoy great conversation, good company, and a relaxing time with fellow readers—we’d love to have you join us!	1 event 10 1 event, 10 6:00 pm - 7:00 pm Recurring Wineo Bingo with Triple H Ranch & Therapeutic Horsemanship July 10 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Triple H Ranch & Therapeutic Horsemanship Join us for Wine-O Bingo with Triple H Ranch & Therapeutic Horsemanship! 🍷🎉 Grab your friends, pour a glass of wine, and get ready to shout “Wine-O!” Enjoy an evening of fun, laughter, and friendly competition while supporting an incredible cause. All donations to play will directly benefit Triple H and the meaningful work they do in our community!	1 event 11 1 event, 11 11:00 am - 12:00 pm Recurring Behind The Vines July 11 @ 11:00 am - 12:00 pm Recurring 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…
1 event 12 1 event, 12 2:00 pm - 4:00 pm Live Music with Fred and Ginger July 12 @ 2:00 pm - 4:00 pm Live Music with Fred and Ginger Join us for live music with Fred and Ginger! Grab a glass of wine and take in the beautiful scenery as they set the vibe with their soulful tunes. Sit back, relax, and enjoy a great afternoon of music, wine, and good company! 🍷🎶	0 events 13 0 events, 13	0 events 14 0 events, 14	1 event 15 1 event, 15 5:30 pm - 6:30 pm Yoga in the Vineyard July 15 @ 5:30 pm - 6:30 pm Yoga in the Vineyard Join us for Yoga in the Vineyard! 🌿🧘‍♀️ All are encouraged to join—whether you’re a first-time yogi or a seasoned pro, we’d love to see you out here. Come unwind, stretch, and soak in the peaceful vineyard views with us! Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your choice. To receive a full refund, please notify our Events Manager at least 14 days in advance by emailing events@timberhillwinery.com. Tickets canceled within 14 days…	0 events 16 0 events, 16	1 event 17 1 event, 17 6:00 pm - 7:00 pm Pub Trivia July 17 @ 6:00 pm - 7:00 pm Pub Trivia Join us for Pub Trivia as we put your knowledge to the test! Gather your friends, grab a glass of your favorite wine, and get ready for a fun evening filled with laughs, friendly competition, and brain-teasing questions. Whether you're a trivia pro or just coming for the fun, there’s something for everyone. Bring your team and see if you have what it takes to claim bragging rights! 🍷🧠🎉	0 events 18 0 events, 18
1 event 19 1 event, 19 2:00 pm - 4:00 pm Live Music with Cyndi Meyer July 19 @ 2:00 pm - 4:00 pm Live Music with Cyndi Meyer Join us for an afternoon of live music with Cyndi Meyer! Grab your favorite glass of wine, sit back, and soak in the beautiful scenery as Cyndi fills the winery with great music and a welcoming atmosphere. Whether you're catching up with friends, enjoying a date afternoon, or simply looking for a relaxing way to spend your day, this is the perfect chance to unwind and enjoy live entertainment. Come sip, relax, and enjoy great tunes, good company, and all…	0 events 20 0 events, 20	0 events 21 0 events, 21	1 event 22 1 event, 22 5:00 pm - 7:00 pm Paint and Sip July 22 @ 5:00 pm - 7:00 pm Paint and Sip Join us for our July Paint & Sip 🎨🍷 Annie from Vannie Gogh will guide you step-by-step as you create this fun and colorful octopus masterpiece. No painting experience is needed—just bring your creativity and get ready for a relaxing evening of wine, laughter, and art. Gather your friends, sip your favorite Timber Hill wine, and leave with a painting you’ll be proud to display! ✨ All painting supplies are included. Spots are limited, so reserve your seat today! 🐙🍷…	1 event 23 1 event, 23 4:00 pm - 7:00 pm Psychic Readings by Brandi July 23 @ 4:00 pm - 7:00 pm Psychic Readings by Brandi Discover what the future holds at Timber Hill Winery! Join us for an afternoon of psychic readings with Brandi. Each 15-minute reading is just $25! 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 readings offer a unique and enlightening experience. Don’t miss this chance to explore what the future may have in store! #PsychicReadings #TimberHillWinery #WineAndWisdom About Brandi: An ethical, professional psychic clairvoyant, Brandi comes with over…	0 events 24 0 events, 24	1 event 25 1 event, 25 6:00 pm - 8:00 pm Live Music with Emily Wendy July 25 @ 6:00 pm - 8:00 pm Live Music with Emily Wendy Join us for an afternoon of live music with Emily Wendy at Timber Hill Winery! 🎶🍷 Sit back, relax, and enjoy great music, award-winning wines, handcrafted cocktails, and beautiful vineyard views. Gather your friends, grab your favorite drink, and spend the evening soaking in the sounds of a talented local artist. 🍇🎵
2 events 26 2 events, 26 10:30 am - 12:00 pm Bouquets and Brunch July 26 @ 10:30 am - 12:00 pm Bouquets and 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…, 2:00 pm - 4:00 pm Live Music with Back2Back Trio July 26 @ 2:00 pm - 4:00 pm Live Music with Back2Back Trio Join us for a relaxing afternoon of live music with Back2Back Trio from 2–4 PM! Settle in with your favorite glass of wine and enjoy smooth acoustic sounds, great vibes, and beautiful vineyard views. Whether you’re stopping in for a tasting, gathering with friends, or just looking for a laid-back Sunday escape, this is the perfect way to spend your afternoon at Timber Hill.	0 events 27 0 events, 27	0 events 28 0 events, 28	0 events 29 0 events, 29	0 events 30 0 events, 30	1 event 31 1 event, 31 6:00 pm - 7:00 pm Reality TV Trivia July 31 @ 6:00 pm - 7:00 pm Reality TV Trivia Your next obsession just dropped... 📺🍷 Grab your fellow binge-watchers and join us for Reality TV Trivia! We'll be testing your knowledge across five drama-filled rounds: 🍸 Bravo favorites ❤️ Dating show drama ✨ Celebrity reality 📺 Reality competition & game shows 🔥 Today's biggest binge-worthy hits Whether you've kept up with the Kardashians, survived Scandoval, know exactly who got "a text," or never miss the latest reality TV buzz, there's something for every fan. Pour yourself a glass, gather…