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.

Painted Wine Glasses Workshop

Name: Painted Wine Glasses Workshop
Start: 2026-06-16T17:00:00-05:00
End: 2026-06-16T19:00:00-05:00
Location: Timber Hill Winery

Join us at Timber Hill Winery as we team up with Craft & Vine for a fun and creative evening where you’ll hand-paint your own set of wine glasses! 🍷✨ They will guide you step-by-step through the featured design, making it easy and enjoyable for all skill levels.

Prefer something more personal? You’re welcome to bring your own inspiration and choose your own colors to make your glasses uniquely yours.All supplies are included, and while they don’t use stencils, you’ll receive live instruction every step of the way to help you feel confident and relaxed as you create.Spots are limited, so grab your girls or plan a cozy date night—be sure to sign up before it’s too late!

Calendar

S	M	T	W	T	F	S
					1 event 1 1 event, 1 6:00 pm - 7:00 pm Recurring Wineo Bingo with Project 16:49 May 1 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Project 16:49 Join us for Wineo Bingo with Project 16:49! 🍷🎉 Come enjoy a fun evening of bingo, great wine, and giving back to a meaningful cause. All donations to play go directly toward Project 16:49 and the incredible work they do to support youth in our community. Grab your friends, sip some wine, and play for a purpose while helping make a difference right here in our community. We can’t wait to see you there! ❤️	0 events 2 0 events, 2
2 events 3 2 events, 3 11:00 am - 2:00 pm Dog Mom Day May 3 @ 11:00 am - 2:00 pm Dog Mom Day 🎉 Our Annual Dog Mom Day is back, and we can’t wait to celebrate with you and your pups! 🐾 We’re teaming up with the amazing Brown Paws Rescue for a day packed with fun, furry friends, and ways to give back. Here’s what’s waiting for you: 🐶 Meet Adoptable Dogs & Enter Fun Raffles – Find your new best friend and support a great cause! 💍 Permanent Jewelry & Matching Dog Collar Charms – Proceeds benefit Brown Paws Rescue.…, 2:00 pm - 4:00 pm Live Music with Jenna Lynne May 3 @ 2:00 pm - 4:00 pm Live Music with Jenna Lynne 🎶 Live Music with Jenna Lynne🍷Kick back and soak up the sunshine as Jenna Lynne fills the air with her soulful tunes! Spend the afternoon on our beautiful patio, sip your favorite Timber Hill wine, and let the music carry you away. Whether you’re catching up with friends, enjoying a relaxing solo outing, or discovering new favorites from our wine selection, this is the perfect way to unwind and celebrate the weekend. Good vibes, great wine, and live music—what more…	1 event 4 1 event, 4 5:30 pm - 7:00 pm Recurring Traditional Bingo with KANDU Grapes and Hops May 4 @ 5:30 pm - 7:00 pm Recurring Traditional Bingo with KANDU Grapes and Hops 🎉 Join us for a Traditional Bingo Night benefiting KANDU Grapes and Hops! Bingo rounds are $5 each, starting at 5:30 PM. Cash is encouraged! Each round’s pot will be split between the winner and KANDU Grapes and Hops, so every game played supports a great cause. Grab a drink, bring your lucky charm, and make your Tuesday night bingo night! 🍷✨	0 events 5 0 events, 5	0 events 6 0 events, 6	2 events 7 2 events, 7 5:00 pm - 7:00 pm Mother’s Day Bouquet Workshop May 7 @ 5:00 pm - 7:00 pm Mother’s Day Bouquet Workshop Celebrate the amazing people in your life at our Mother’s Day Bouquet Workshop! 🌸 Bring a friend, family member, or someone who does it all—even fur moms! Your ticket includes all the flowers and supplies you need to create a beautiful bouquet 💐 to take home. Sip, craft, and celebrate the ones who make life brighter! Disclaimer: If you are unable to attend, your ticket may be transferred to a guest of your choice. To receive a full refund, please…, 6:00 pm - 7:00 pm Book Club May 7 @ 6:00 pm - 7:00 pm Book Club May Book: My Husband's Wife by Alice Feeney Join us this month as we dive into My Husband's Wife by Alice Feeney! Gather with fellow readers to discuss twists, turns, and all the suspense this gripping story has to offer. Whether you’re a longtime book club member or just curious, all are welcome to join the conversation!	1 event 8 1 event, 8 6:00 pm - 7:00 pm Boy Band Trivia May 8 @ 6:00 pm - 7:00 pm Boy Band Trivia Join us on May 8th for Boy Band Trivia Night! 🎤✨ We’re teaming up with Premier Giving Foundation to bring you the ultimate throwback trivia experience. Entry is donation-based, with all proceeds going directly to support their mission. Plus, we’ll have plenty of exciting raffles throughout the night to keep the fun going and give you even more chances to win! Grab your crew, brush up on your boy band knowledge, and get ready for a night of music, memories,…	0 events 9 0 events, 9
1 event 10 1 event, 10 2:00 pm - 4:00 pm Live Music with Andy Braun May 10 @ 2:00 pm - 4:00 pm Live Music with Andy Braun Join us for an afternoon of live music with Andry Braun! 🎶 Bring your friends, relax on the patio, and sip your favorite wine as the tunes carry you away. It’s the perfect way to unwind and enjoy a beautiful day! 🍷	0 events 11 0 events, 11	0 events 12 0 events, 12	1 event 13 1 event, 13 5:00 pm - 7:00 pm Geometric Blooms Workshop May 13 @ 5:00 pm - 7:00 pm Geometric Blooms Workshop Join us for a relaxed and creative evening at Timber Hill Winery as we create a beautiful spring-inspired framed wood sign! Guests will choose one of two coordinating designs — a geometric mason jar bouquet or a geometric watering can floral arrangement — both featuring layered wood pieces, your custom picked color scheme, and a stained wood outline for a polished, high-end finish. Participants will paint and assemble their 8" x 10" framed sign using pre-cut wooden pieces, making this…	0 events 14 0 events, 14	0 events 15 0 events, 15	2 events 16 2 events, 16 11:00 am - 12:00 pm Recurring Behind the Vines May 16 @ 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…, 2:00 pm - 3:00 pm Behind the Vines May 16 @ 2:00 pm - 3:00 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…
2 events 17 2 events, 17 2:00 pm - 4:00 pm Live Music with Bill Conway May 17 @ 2:00 pm - 4:00 pm Live Music with Bill Conway Join us for live music with Bill Conway! 🎸 Grab your friends, sip on your favorite wine, and let the smooth sounds of Bill set the perfect vibe for your day. Cheers to great music and even better company! 🍷, 2:00 pm - 5:00 pm Kitten Shower May 17 @ 2:00 pm - 5:00 pm Kitten Shower Calling all cat lovers! 🐱✨ Come celebrate our furry friends at the Kitten Shower with the Humane Society of Southern Wisconsin! Adorable adult cats & kittens available for adoption – your purr-fect companion could be waiting! Donations encouraged – because every whisker deserves a little love. Volunteer & foster education opportunities – learn how YOU can help more paws find their forever homes. 💌 Have a favorite item you love to donate? Check out the Humane Society’s wish list while…	1 event 18 1 event, 18 5:00 pm - 7:00 pm Sourdough Workshop May 18 @ 5:00 pm - 7:00 pm Sourdough Workshop Join us for a Sourdough Workshop! Margaret from Blue Bird Custom Creations will guide you step-by-step through everything you need to become a sourdough pro! Learn how to care for your starter, master the basics of sourdough baking, and leave ready to bake at home with everything included: A live sourdough starter Detailed instructions and tried-and-true recipes A ready-to-bake loaf of sourdough bread Whether you’re a beginner or just looking to improve your skills, this hands-on workshop is perfect for all bread…	1 event 19 1 event, 19 5:00 pm - 7:00 pm Herb Planting Workshop May 19 @ 5:00 pm - 7:00 pm Herb Planting Workshop 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 after 14 days will not be refunded. get your tickets here	0 events 20 0 events, 20	0 events 21 0 events, 21	1 event 22 1 event, 22 6:00 pm - 7:00 pm 90s Trivia with Made New Dog Rescue May 22 @ 6:00 pm - 7:00 pm 90s Trivia with Made New Dog Rescue Join us as we dive into 90s Trivia Night! Grab your team and get ready to test your knowledge on all things 90s—from music and movies to pop culture throwbacks. 📼🎶 The best part? It’s all for a great cause! All donations to play will directly benefit Made New Dog Rescue. 🐾 We’ll also have raffles and a 50/50 drawing available to keep the fun going and help raise even more for the pups. Bring your friends, brush up on…	0 events 23 0 events, 23
1 event 24 1 event, 24 2:00 pm - 4:00 pm Live music with Brooke Nunn May 24 @ 2:00 pm - 4:00 pm Live music with Brooke Nunn Join us for live music with Brooke Nunn! 🎶 Grab your friends, find a cozy spot, and sip on your favorite wine while enjoying an afternoon of great music. Brooke will be bringing the perfect soundtrack for a relaxing day at the winery. Whether you're catching up with friends or just looking for a laid-back way to spend the day, this is the perfect excuse to sit back, unwind, and let the music set the vibe. Cheers to good wine,…	0 events 25 0 events, 25	1 event 26 1 event, 26 5:00 pm - 7:00 pm Paint and Sip May 26 @ 5:00 pm - 7:00 pm Paint and Sip 🎨🍷 Join us for a magical May Paint & Sip at Timber Hill Winery! Grab your friends, sip on your favorite wine, and get creative as Annie guides you step-by-step through painting this adorable gnome mushroom masterpiece. No experience needed — just come ready for a fun and relaxing evening filled with creativity, laughter, and wine! Seats are limited, so grab your tickets today and join us for a cozy springtime night at the winery! Disclaimer: If you are unable…	0 events 27 0 events, 27	1 event 28 1 event, 28 4:00 pm - 7:00 pm Aura Paintings May 28 @ 4:00 pm - 7:00 pm Aura Paintings 🔮✨ Aura Paintings with Psychic Readings by Brandi Join us for a unique and creative experience where energy becomes art. Brandi will connect with your aura and intuitively paint what she sees—translating your energy, colors, and emotional presence into a one-of-a-kind piece of artwork made just for you. No tickets are required. Aura Paintings will be available on a first come, first served basis. Each guest will receive their own small aura painting to take home as a personal keepsake.…	0 events 29 0 events, 29	0 events 30 0 events, 30
2 events 31 2 events, 31 10:30 am - 1:00 pm Bouquets & Brunch May 31 @ 10:30 am - 1:00 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. It’s the perfect way to sip, snack, and get creative together! Disclaimer: If you are unable to attend, your…, 2:00 pm - 4:00 pm Live Music with Two for the River May 31 @ 2:00 pm - 4:00 pm Live Music with Two for the River Join us for live music with Two for the River! 🎶 From 2:00–4:00 PM, they’ll be filling the afternoon with beautiful acoustic sounds and easygoing favorites that are perfect for a relaxing day at the winery. Grab a glass of your favorite wine, find a cozy spot with friends, and enjoy the laid-back atmosphere as the music sets the tone for a fun and memorable afternoon. Whether you’re stopping in for a tasting or staying a while, it’s the perfect…