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.

Fall Sip and Shop

Name: Fall Sip and Shop
Start: 2026-11-22T12:00:00-06:00
End: 2026-11-22T16:00:00-06:00
Location: Timber Hill Winery

🍂 Fall Sip & Shop Bus Trip 🛍️

Grab your friends and join us for a fun-filled afternoon of shopping, sipping, and supporting local businesses! 🍁 Join us on November 22nd for our Fall Sip & Shop Bus Trip, starting at Timber Hill Winery in Milton, WI.

Enjoy an afternoon exploring local shops, discovering unique finds, and taking advantage of exclusive deals along the way. With convenient bus transportation and a special shopping passport included with your ticket, you can sit back, relax, and enjoy a stress-free day out! 🛍️

🎟️ Tickets: $25 per person Your ticket includes bus transportation and a special passport filled with exclusive, one-day-only deals and discounts at participating shops!

🛍️ Participating Bus Stops & Shops

Junction Shops:

Sunny and Olive
The Painted Turtle

Parkview Shops:

Rubber Ducky Winery
Pene Jenta
Hattie and Elsie
2nd Time Around
Good Works Brewing Co.
Elmside Goods

🚌 Sip & Shop Shuttle Details

Shopping Hours: 12:00pm – 4:00pm
All shuttles begin and return to Timber Hill Winery.
Buses will run in a continuous loop throughout the event.

Junction Shops Bus Stop 📍 Merchant Row Parking Lot

Parkview Shops Bus Stop 📍 Parking lot across from College St.

✨ Space is limited, so grab your ticket and join us for a day of shopping, sipping, and fall fun!

#FallSipAndShop #TimberHillWinery #ShopMiltonWI #ShopLocal

Ticket Disclaimer: If you are unable to attend, your ticket may be transferred to a guest. To receive a full refund, please notify our Events Manager at least 14 days before the event by emailing events@timberhillwinery.com. Tickets canceled within 14 days of the event will not be refunded.

Calendar

S	M	T	W	T	F	S
				1 event 1 1 event, 1 5:30 pm - 7:00 pm Purse Bingo October 1 @ 5:30 pm - 7:00 pm Purse Bingo 🎉 Purse Bingo Night! 🎉 Join us for a fun-filled evening of Purse Bingo, where all prizes are stylish purses! 👜✨ For just $25, you can play as many rounds as we can fit from 5:30 PM – 7:00 PM. ⏰ Can’t make it at 5:30? No worries! Jump in at the next starting round—don’t miss the fun. 🎟️ Tickets are required, so grab yours today and get ready for a night of prizes, laughs, and good times! Disclaimer: If…	1 event 2 1 event, 2 6:00 pm - 7:00 pm Recurring Wineo Bingo with Friends of Noah October 2 @ 6:00 pm - 7:00 pm Recurring Wineo Bingo with Friends of Noah 🍷🐾 Wineo Bingo with Friends of Noah! 🐾🍷 Join us for a fun night of Wineo Bingo while supporting an amazing local organization! Grab a glass of wine, bring your friends, and test your luck during bingo. 🎉 All donations to play directly benefit Friends of Noah and the incredible work they do to help animals in need. Every little bit makes a difference! Come sip, play, and support a great cause! ❤️ We’ll see you at Timber Hill Winery!	1 event 3 1 event, 3 11:00 am - 12:00 pm Behind the Vines October 3 @ 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…
1 event 4 1 event, 4 2:00 pm - 4:00 pm Live Music with Matt Andrus October 4 @ 2:00 pm - 4:00 pm Live Music with Matt Andrus 🎶 Live Music with Matt Andrus 🎶 Join us at Timber Hill Winery for an afternoon of live music with Matt Andrus! Grab a glass of your favorite Timber Hill wine, relax with friends, and enjoy live music in a beautiful winery setting. 🍷 Sip, relax, and enjoy the music! We can’t wait to see you at Timber Hill Winery!	0 events 5 0 events, 5	1 event 6 1 event, 6 11:00 am - 7:00 pm Stormy’s Takeover at Timber Hill Winery October 6 @ 11:00 am - 7:00 pm Stormy’s Takeover at Timber Hill Winery 🧀 Stormy’s Takeover at Timber Hill Winery! 🍷 Our kitchen will be closed all day on October 6th, but we’ve got you covered! In honor of our upcoming 10th Anniversary, we’re taking it back with a special Stormy’s Takeover at Timber Hill Winery! 🎉 Stormy’s will be joining us with their delicious grilled cheese creations, mac & cheese, and other comfort food favorites. It’s the perfect pairing for a glass of Timber Hill wine! 📅 Tuesday, October 6th 📍 Timber…	1 event 7 1 event, 7 5:00 pm - 7:00 pm Broom Bar October 7 @ 5:00 pm - 7:00 pm Broom Bar You’ll start with the base broom and then head to our Broom Bar to choose from an assortment of accents to make it completely your own. Mix, layer, wrap and embellish using a variety of seasonal materials such as: Fall & Halloween florals and greenery Dried and natural elements Moss, leaves and berries Ribbons, lace and fabric Feathers Spooky charms & mini accents Twine and other decorative goodies Go witchy and spooky, moody and mystical, or warm and fall-inspired—there’s no right or wrong…	0 events 8 0 events, 8	1 event 9 1 event, 9 6:00 pm - 7:00 pm Pub Trivia October 9 @ 6:00 pm - 7:00 pm Pub Trivia 🍻 Pub Trivia at Timber Hill Winery! 🧠 Put your knowledge to the test and join us for a fun night of Pub Trivia at Timber Hill Winery! Gather your team, enjoy your favorite wine, and see if you have what it takes to claim the top spot. From pop culture and music to history, sports, and everything in between, you never know what questions will come your way!	1 event 10 1 event, 10 2:00 pm - 7:00 pm Timber Hill’s 10-Year Anniversary Celebration October 10 @ 2:00 pm - 7:00 pm Timber Hill’s 10-Year Anniversary Celebration Join us as we celebrate 10 years of Timber Hill Winery! What began with Amanda’s vision and determination has grown into a place where people gather, celebrate, and feel at home. Now, we’re celebrating a decade of Timber Hill with wine, music, good food, and an unforgettable Catalina Wine Mixer experience. Live Music• Sweet n Sour Duo \| 2–4 PM• Nauti Nauti \| 4–7 PM VIP Anniversary Experience \| $25Upgrade your celebration! VIP ticket includes:• Exclusive 10th Anniversary Gift Bag• Taste of…
1 event 11 1 event, 11 10:30 am - 12:00 pm Live Music with Bree Morgan October 11 @ 10:30 am - 12:00 pm Live Music with Bree Morgan 🎶 Live Music with Bree Morgan 🍷 Join us at Timber Hill Winery for an afternoon of live music with Bree Morgan! Enjoy great wine, delicious food, and live music in a relaxed winery setting. Grab your friends, find a seat, and settle in for a fun time at Timber Hill! 🍇	0 events 12 0 events, 12	1 event 13 1 event, 13 5:30 pm - 7:00 pm Cookie Cake Decorating Workshop October 13 @ 5:30 pm - 7:00 pm Cookie Cake Decorating Workshop 🍂 October Cookie Cake Decorating Workshop 🍪 Join us at Timber Hill Winery for a fun and creative October Cookie Cake Decorating Workshop! 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 decorate your own 8" chocolate chip cookie cake with festive fall-inspired buttercream designs. Our instructor will guide you step-by-step, making it easy, creative, and enjoyable for everyone!…	0 events 14 0 events, 14	2 events 15 2 events, 15 6:00 pm - 7:00 pm Book Club October 15 @ 6:00 pm - 7:00 pm Book Club 📖 October Book: This Book Made Me Think of You by Libby Page 📚✨ Book Club at Timber Hill Winery – October Edition ✨📚 Join us this October for Book Club as we gather to discuss This Book Made Me Think of You by Libby Page! 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…, 6:00 pm - 7:00 pm Book Club October 15 @ 6:00 pm - 7:00 pm Book Club October Book: This Book Made Me Think of You by Libby Page Join us for our October Book Club as we dive into This Book Made Me Think of You by Libby Page! A heartfelt story about friendship, connection, and the unexpected ways books can bring people together, this charming read is sure to inspire plenty of conversation. Grab a glass of wine and settle in for an evening of good books, great company, and thoughtful discussion. Whether you’re a…	0 events 16 0 events, 16	0 events 17 0 events, 17
2 events 18 2 events, 18 12:00 pm - 4:00 pm Birds of a Feather Booktique October 18 @ 12:00 pm - 4:00 pm Birds of a Feather Booktique 📚 Join us this Sunday for a fun collaboration with Birds of a Feather Booktique! From 12pm to 4pm, their mobile bookstore will be parked at the winery, ready for you to browse, discover your next great read, and shop some new favorites. 📖🍷 Grab a glass of wine, explore the books, and enjoy a relaxing Sunday with us. We can’t wait to see you!, 2:00 pm - 4:00 pm Live Music with Tim O’Grady October 18 @ 2:00 pm - 4:00 pm Live Music with Tim O’Grady 🎶 Tim O'Grady is Live at Timber Hill! 🍷 Spend some time at the winery and enjoy an afternoon of live music from Tim O'Grady. Sip your favorite Timber Hill wine, grab a bite to eat, and enjoy the music while taking in the winery atmosphere. Make a day of it and join us for live music, wine, and good company! 🍇	0 events 19 0 events, 19	1 event 20 1 event, 20 5:00 pm - 7:00 pm Paint and Sip October 20 @ 5:00 pm - 7:00 pm Paint and Sip 🎨 October Paint & Sip is here! 🎃 Grab your tickets before it’s too late! Annie from Vannie Gogh will guide you step-by-step as you create your very own pumpkin masterpiece. Enjoy a fun afternoon of painting, wine, and good company at Timber Hill Winery! Ticket Policy: If you’re unable to attend, your ticket may be transferred to a guest of your choice. For a full refund, please notify our Events Manager at least 14 days in advance by emailing events@timberhillwinery.com. Tickets canceled less…	0 events 21 0 events, 21	0 events 22 0 events, 22	1 event 23 1 event, 23 6:00 pm - 7:00 pm Hocus Pocus Trivia October 23 @ 6:00 pm - 7:00 pm Hocus Pocus Trivia 🔮 Hocus Pocus Trivia 🧙‍♀️ It’s just a bunch of Hocus Pocus! Gather your favorite witches, brush up on your Sanderson Sisters knowledge, and join us for a night of spooky fun at Timber Hill Winery. From Salem to the spellbook, we’ll put your Hocus Pocus knowledge to the test with questions covering all your favorite characters, quotes, moments, and magical mischief from the movie. Grab your crew, pick a team name, and see if you have what it takes…	0 events 24 0 events, 24
1 event 25 1 event, 25 2:00 pm - 4:00 pm Live Music with Cyndi Meyer October 25 @ 2:00 pm - 4:00 pm Live Music with Cyndi Meyer 🎤 An Afternoon with Cyndi Meyer 🍷 There’s nothing better than a glass of wine, a beautiful winery setting, and live music to enjoy with friends. Join us at Timber Hill Winery as Cyndi Meyer takes the stage! Come hungry, come thirsty, and stay awhile. We’ll have the wine flowing and Cyndi providing the soundtrack. 🍇🎶	1 event 26 1 event, 26 3:00 pm - 7:00 pm Chunky Knit Blanket Workshop October 26 @ 3:00 pm - 7:00 pm Chunky Knit Blanket Workshop Register using the links below. After you click BOOK check the date (Oct 26) and the time (3pm) Join us for a fun evening making cozy blankets! 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…	0 events 27 0 events, 27	0 events 28 0 events, 28	1 event 29 1 event, 29 4:00 pm - 7:00 pm Tarot Readings with Brandi October 29 @ 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.…	0 events 30 0 events, 30	0 events 31 0 events, 31