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.

Hall Pass to Happy Hour

Name: Hall Pass to Happy Hour
Start: 2026-03-26T00:00:00-05:00
End: 2026-03-26T23:59:59-05:00
Location: Timber Hill Winery

Calling All Teachers! 🍷✨

It’s time to turn in your hall pass… for a better one!

Join us for Hall Pass to Happy Hour and enjoy spring break the right way — no lesson plans, no grading, just time to rewind, recharge, and relax.

Enjoy our Happy Hour specials while you’re here, and receive a free entry into our 🎟️ pizza party giveaway for your class with every purchase — up to six pizzas 🍕 and garlic bread 🥖, courtesy of Timber Hill Winery. Must show teacher ID at checkout to enter.

This special is available to teachers from Janesville, Milton, Whitewater, Jefferson, and Edgerton.

Because you deserve a break… and maybe a glass (or two). 💛

Calendar

S	M	T	W	T	F	S
1 event 1 1 event, 1 2:00 pm - 4:00 pm Live Music with Steve Weber March 1 @ 2:00 pm - 4:00 pm Live Music with Steve Weber Join us for live music with Steve Weber at Timber Hill! 🎶 Grab a glass of your favorite wine, bring your friends, and settle in for a laid-back day filled with great tunes, good company, and vineyard vibes as Steve sets the soundtrack for your visit!	1 event 2 1 event, 2 3:00 pm - 7:00 pm Chunky Knit Blanket Workshop March 2 @ 3:00 pm - 7:00 pm Chunky Knit Blanket Workshop Register using the links below. After clicking BOOK, select March 2nd and the 3:00 PM time slot. Join us for a cozy and creative evening of chunky knit blanket making—paired with great food and delicious drinks! 🧶🍷This hands-on workshop is perfect for beginners and experienced knitters alike. No needles required—we’ll knit using just our hands. Everyone goes home with a finished blanket in a blanket bag, plus emailed instructions and yarn-buying tips for future projects. We’ll be making lap blankets…	1 event 3 1 event, 3 5:00 pm Traditional Bingo with Project 16:49 Lip Sync March 3 @ 5:00 pm Traditional Bingo with Project 16:49 Lip Sync Join us for a Traditional Bingo Night benefiting Project 16:49 Lip Sync Fundraising! Bingo rounds are $5 each, starting at 5:00 PM. Cash is encouraged! Each round’s pot will be split between the winner and Project 16:49, so every game played supports a great cause. And that’s not all! We’ll also have a 50/50 raffle, giving you even more chances to win while supporting Project 16:49. Grab a drink, bring your lucky charm, and make your Tuesday night bingo night!	0 events 4 0 events, 4	0 events 5 0 events, 5	1 event 6 1 event, 6 6:00 pm - 7:00 pm Recurring Wineo Bingo with Rock County Cancer Coalition March 6 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Rock County Cancer Coalition Join us for an evening of Wineo Bingo benefiting Rock County Cancer Coalition! 🍷🎉 Get ready to sip, play, and shout WINEO! at the first sight of Bingo. The best part? All donations to play go directly to support the Rock County Cancer Coalition and the important work they do in our community. Bingo will start being called at 6:00 PM and wrap up at 7:00 PM, so come early, grab a glass, and get ready for a fun-filled evening…	0 events 7 0 events, 7
1 event 8 1 event, 8 2:00 pm - 4:00 pm Live Music with Tim O’Grady March 8 @ 2:00 pm - 4:00 pm Live Music with Tim O’Grady 🎶 Live Music with Tim O’Grady at Timber Hill! 🍷Grab a glass, gather your friends, and spend an afternoon enjoying Tim O’Grady’s tunes in the beautiful winery setting. Relax, sip, and soak in the music as we fill the vineyard with good vibes and great company—perfect for a casual outing or a fun hangout with friends!	0 events 9 0 events, 9	1 event 10 1 event, 10 5:30 pm - 6:30 pm Girl Scout Cookie and Wine Pairing March 10 @ 5:30 pm - 6:30 pm Girl Scout Cookie and Wine Pairing Join us for a Girl Scout Cookie & Wine Pairing! 🍷🍪 Sip, savor, and enjoy perfectly paired wines and cookies. The best part? A Girl Scout will be on-site selling cookies, so you can stock up on all your favorites to take home! Grab your tickets today! 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…	0 events 11 0 events, 11	1 event 12 1 event, 12 6:00 pm - 7:00 pm Book Club March 12 @ 6:00 pm - 7:00 pm Book Club March Book: The White Octopus Hotel by Alexandra Bell Join us for our March Murder Mystery as we dive into The White Octopus Hotel by Alexandra Bell. This thrilling read is full of suspense, secrets, and twists that are sure to keep you guessing. Whether you’re a seasoned reader or just getting back into reading, everyone is welcome to join the discussion and enjoy a great night of mystery and conversation.	1 event 13 1 event, 13 6:00 pm - 7:00 pm How I Met Your Mother Trivia March 13 @ 6:00 pm - 7:00 pm How I Met Your Mother Trivia 💛 How I Met Your Mother Trivia Night! 💛 Think you know the story of Ted, Robin, Barney, and the gang? Grab your teammates and join us for a night full of laughs, challenges, and nostalgia as we dive into the epic romance of Ted and Robin—and all the legendary moments that made How I Met Your Mother a fan favorite! From the slap bet to the pineapple incident, from rooftop proposals to barroom shenanigans, this trivia night will test…	2 events 14 2 events, 14 11:00 am - 12:00 pm Recurring Behind the Vines March 14 @ 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 March 14 @ 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 15 2 events, 15 10:30 am - 1:00 pm Bouquets and Brunch March 15 @ 10:30 am - 1:00 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 🥞 Brunch & Drinks: Sold separately — reserve your brunch spot here https://timberhillwinery.com/sunday-brunch-buffet/ It’s the perfect way to sip, snack, and get creative together! Disclaimer: If you are unable to attend, your ticket may…, 2:00 pm - 4:00 pm Live Music with Evan Pingel March 15 @ 2:00 pm - 4:00 pm Live Music with Evan Pingel Join us for an evening of live music with Evan Pingel! 🎶🍷 Sit back, sip your favorite wine, and enjoy a laid-back night filled with great music and welcoming vibes. It’s the perfect way to unwind and spend the evening with friends.	0 events 16 0 events, 16	1 event 17 1 event, 17 5:00 pm - 6:30 pm Staff Cocktail Pour-Off Herd Social March 17 @ 5:00 pm - 6:30 pm Staff Cocktail Pour-Off Herd Social 🍹 Join us for the 2026 Staff Cocktail Pour-Off! The herd is invited to sip, taste, and vote on your favorite staff-created cocktails! 🎉 Each ticket includes: ✨ Samples of our staff’s delicious creations 🗳️ A voting card to cast your vote 🏆 The winning cocktail will be crowned Cocktail of the Month for April! Come help us pick the champion cocktail and enjoy a fun, tasty afternoon with your herd! 🥂💃 Herd members are welcome to bring guests, but…	0 events 18 0 events, 18	1 event 19 1 event, 19 7:30 pm - 9:00 pm Comedy March 19 @ 7:30 pm - 9:00 pm Comedy 🎤 Comedy Night at Timber Hill! 🎤Get ready to laugh until your cheeks hurt! Join us for an evening of side-splitting stand-up, witty one-liners, and hilarious stories from some of the funniest comedians around. Whether you’re coming with friends, a date, or flying solo, this is the perfect night to unwind, sip your favorite wine, and let the laughs flow!Comedy Night seating is assigned! If you’re planning to sit with someone whose ticket you purchased separately, please email our Events…	0 events 20 0 events, 20	1 event 21 1 event, 21 6:00 pm - 9:00 pm The Office Murder Mystery March 21 @ 6:00 pm - 9:00 pm The Office Murder Mystery Join us for The Office Murder Mystery! Someone’s been murdered… and it’s definitely not a prank by Jim. 🖇️Channel your inner Dwight, question everyone, and find out who’s done it. Tickets are priced at $55 per person and include the murder mystery game, and dinner. Wine and beer will be available for purchase. This event is for adults only, 21 years and older. Dinner will be served buffet style with a Garden Salad, Garlic Chicken with Mashed Potatoes and Mixed…
2 events 22 2 events, 22 2:00 pm - 4:00 pm Live Music with Noah James Hittner March 22 @ 2:00 pm - 4:00 pm Live Music with Noah James Hittner 🎶 Live Music with Noah James Hittner! 🎶 Join us for an afternoon of great vibes, amazing music, and your favorite Timber Hill wines! Noah James Hittner will be bringing his soulful tunes and captivating performance to our cozy winery setting! Sip, snack, and sway along to the music as Noah fills the room with energy, emotion, and unforgettable melodies. 🍷🎸, 2:00 pm - 4:00 pm Project 16:49 Lip Sync Donor Appreciation March 22 @ 2:00 pm - 4:00 pm Project 16:49 Lip Sync Donor Appreciation Join us for our Donor Party! 🎉 We want to say a huge THANK YOU to everyone who has donated in support of Timber Hill Winery’s Project 16:49 Lip Sync. A donation of $50 or more per person earns you entry to our exclusive Donor Party, which includes delicious hors d’oeuvres and one specialty cocktail! 🍷✨ Come celebrate with us—we can’t wait to raise a glass to you! 💛 Make a Donation Here - https://project1649.org/lip-sync-battle/donate/timber-hill-dazzlers/	1 event 23 1 event, 23 5:00 pm - 7:00 pm Spring Doormat Workshop March 23 @ 5:00 pm - 7:00 pm Spring Doormat Workshop 🎨🚪Join us for a fun and creative Spring workshop where you’ll design and hand-paint your very own seasonal doormat! There’s no better way to welcome fresh air, blooming days, and guests who are finally emerging from winter hibernation than with a one-of-a-kind spring-themed mat made by you. Whether you’re a seasoned crafter or just looking for a relaxing and creative outing, this workshop is perfect for all skill levels. All supplies are provided, and spots are limited—so be sure to…	0 events 24 0 events, 24	1 event 25 1 event, 25 5:30 pm - 6:30 pm Dessert & Dirty Soda Pairing March 25 @ 5:30 pm - 6:30 pm Dessert & Dirty Soda Pairing 🍰🥤 Dessert & Dirty Soda Pairing at Timber Hill Winery!Treat yourself to a sweet and bubbly experience! Enjoy four decadent desserts, each thoughtfully paired with one of our signature dirty sodas for a fun twist on flavor. This event is all ages encouraged, so bring the whole family or a group of friends for a unique tasting adventure. Laugh, sip, and savor every bite as you indulge in this playful and delicious experience!Disclaimer: If you are unable to attend, your…	1 event 26 1 event, 26 2026-03-26 Hall Pass to Happy Hour Hall Pass to Happy Hour March 26 Hall Pass to Happy Hour Calling All Teachers! 🍷✨ It’s time to turn in your hall pass… for a better one! Join us for Hall Pass to Happy Hour and enjoy spring break the right way — no lesson plans, no grading, just time to rewind, recharge, and relax. Enjoy our Happy Hour specials while you’re here, and receive a free entry into our 🎟️ pizza party giveaway for your class with every purchase — up to six pizzas 🍕 and garlic bread 🥖, courtesy…	1 event 27 1 event, 27 6:00 pm - 7:00 pm Harry Potter Trivia March 27 @ 6:00 pm - 7:00 pm Harry Potter Trivia 🪄 Attention All Wizards, Witches, and Muggles! Think you know everything about the magical world of Harry Potter? It’s time to put your knowledge to the ultimate test! Join us for Harry Potter Trivia at Timber Hill Winery, where teams will compete in a fun, spellbinding battle of wits. From Hogwarts houses to magical creatures, spells, and the darkest corners of the wizarding world, no detail is too small — so study up! ✨	0 events 28 0 events, 28
1 event 29 1 event, 29 2:00 pm - 4:00 pm Live Music with Matt Jaye March 29 @ 2:00 pm - 4:00 pm Live Music with Matt Jaye 🎶✨ Join us for an unforgettable afternoon with live music by Matt Jaye! 🎸🍷 Let the smooth sounds and good vibes fill your weekend as you sip on your favorite wine and unwind with friends. You won’t want to miss this! 🥂🎵	0 events 30 0 events, 30	1 event 31 1 event, 31 5:00 pm - 7:00 pm Paint and Sip March 31 @ 5:00 pm - 7:00 pm Paint and Sip 🎨 March Paint & Sip 🍷 Join us for a fun, creative evening! Annie from Vannie Gogh will guide you step-by-step as you create your own masterpiece.✨ Spots are limited, so grab your tickets before they’re gone! 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…