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.

May 2022
Weekly Winery Update
We will have virtual happy hour on our Facebook and YouTube LIVE Wednesdays at 8pm! We are going to walk you through upcoming events and things happening 'at the winery', and check in with some of our staff that you may be missing! We hope you can join us! If you have questions please feel free to ask them live or comment on the Facebook live!
Find out more »May Wine and Yoga
May Wine and Yoga is May 19th at 6pm!Whether you are a seasoned yogi or if you haven’t tried Yoga before, this is your class! Come let go of stresses and unwind with Yoga and Wine! Elise makes each session unique, beginner-friendly, and enjoyable. This will be a special yoga that’s nice and relaxing with lots of ‘gratitude’! Get your tickets by clicking here before they are gone! Yoga Tickets
Find out more »Wineo Bingo Supporting Webs of Grief
Wineo Bingo Supporting Webs of Grief is May 6th and 20th at 6pm! "Webs of Grief, Inc. is a nonprofit organization dedicated to providing therapeutic resources and facilitating healing experiences for individuals who have experienced the tragic death of a loved one. Where did the name Webs of Grief come from? It was our intent to incorporate our last name into the name of the nonprofit somehow. That was done with the name Webs, but the word Webs serves a…
Find out more »Succulent Planting with Geske’s Gardens
Timber Hill is partnering with Geske's Gardens out of Milton, WI to bring you a Sunday of succulent planting and wine! Your ticket includes the following: 3 succulent plants, a decorative pot, and dirt. Please arrive at 11am for this event! Tickets
Find out more »Back2Back Live Music Acoustic Duo
Join us for Live Music with Back2Back Acoustics as Jim O’Connor & Christine Anderson will be at Timber Hill on May 22nd from 2-4pm! Back2Back covers a wide variety of artists and musical styles including rock, folk-rock, pop and a bit of country. You’ll hear songs by The Beatles, Michael Jackson, James Taylor, The Civil Wars, Fleetwood Mac, and more. They use a wide range of instruments including the following: Acoustic Guitar, Resonator Guitar, Square Neck Dobro, Ukulele, Keyboard, Hand…
Find out more »Comedy Show
Join us for a comedy show at Timber Hill Winery on May 26th at 7:30pm!This show will be hosted by Christiane West, our very own Tasting Room Manager! There will be 3 different comedians along with Christiane that night. Be sure to purchase your tickets now as there is limited availability for the show!Purchase your ticket now by clicking the button below! Tickets
Find out more »Sitcom Trivia
Sitcom Trivia is May 13th & 27th at 6pm! This is free to play and the winning team gets a prize! Categories include: Audio Round The Office Modern Family Fiends Parks & Rec Big Bang Theory Picture Round
Find out more »Thistle + Elm Pop-Up Shop
Thistle + Elm Pop-Up is May 29th from 1-4pm! We've got a dreamy day planned for you! grab all of your favorite gals + join us for a gorgeous afternoon at Timber Hill Winery! Stop in for a glass of your favorite Timber Hill wine, shop Thistle + Elm's collection of carefully curated, on-trend, neutral styles + enjoy the live music!
Find out more »Live Music with Jenna Lynne
Come enjoy Live Music with Jenna Lynne! She does everything from the Beatles to Taylor Swift. She also won Waukesha Idol, twice!! She is an up and coming artist who does everything from the Beatles to Taylor Swift. She also won Waukesha Idol, twice! You won't want to miss out! She will be on our patio from 2-4pm!
Find out more »Professional Women’s Networking Night
Join Katie Myers from State Farm and Timber Hill Winery for our monthly Professional Women's Networking Night. Hear from keynote speakers, build connections and mingle with like minded business owners. The Topic: "Who Am I? - Learning to Break the Labels and Process Personal and Professional Growth" with Keynote Speaker Amanada Torres Due to limited space, we are requiring a $5 admission fee. Everything raised from the May Networking will be donated to Web's Of Grief. Web's of Grief is…
Find out more »June 2022
Live Music with Cyndi Meyer
Local musician Cyndi Meyer will be singing all your favorites! Join us for live music from 3-5pm! Cyndi has an amazing voice and you may recognize her from her band The Rainbow Bridge. She puts on a great show and we love having her! You can't go wrong with music and wine! Stop by Saturday, June 4th to catch Live Music with Cyndi Meyer at the winery!
Find out more »Live Music with Gary the Band
They're back!! Live Music with Gary the Band will be at Timber Hill Winery from 2-4pm! Formed in 2012, Gary the band brings a unique sound to the Southern Wisconsin area, basing their approach on vocal harmonies and tasteful guitar work. With all members of the band sharing the duties of vocals, guitar, and percussion, Gary the Band is able to play a diverse selection of music including classic and modern Pop, Rock, Folk and more. Combining individual studio albums…
Find out more »Live Music With Bree Morgan!
Live Music with Bree Morgan is Sunday, June 12th from 2-4pm! Bree Morgan (link to website) has always known that she was meant to be a musician. You can tell by the passion in her voice that she loves what she does. Since she was just a child, music was in her blood. From listening and rapping to her mom’s hip hop CDs, singing along to Shania Twain or a rock/ pop song on the radio, or even playing around…
Find out more »Live Music with Dan Brusky
Live Music with Dan Brusky is back on June 18th from 3-5pm! Local guitarist and vocalist, Dan Brusky, has been entertaining audiences for over 20 years. His unique interpretations of songs by such artists as Foo Fighters, Eagles, Stone Temple Pilots, Darius Rucker (Hootie), Doobie Brothers, Maroon 5, Zac Brown Band, Johnny Cash, Michael Jackson, and many others, is sure to keep you entertained. Dan will be here from 3-5pm, so come hangout on the patio for an afternoon of…
Find out more »Live Music with Tim O’Grady
Join us on our patio for Live Music and enjoy a glass (or bottle) and snacks or dinner while you enjoy Live Music with Tim O'Grady! Tim is a local musician that covers country music. Check out more about Tim and where he will be by visiting his website or Facebook!
Find out more »July 2022
Live Music with Cyndi Meyer
Local musician Cyndi Meyer will be singing all your favorites! Join us for live music from 2-4pm! Cyndi has an amazing voice and you may recognize her from her band The Rainbow Bridge. She puts on a great show and we love having her! You can't go wrong with music and wine! Stop by Sunday, July 10th to catch Live Music with Cyndi Meyer at the winery!
Find out more »Live Music with Charlie Anne
Charlie Anne will be here with Live Music on the patio from 3-5pm! Charlie Anne is a duo who met through their love of music. They play a range of music that is perfect for sipping wine on the patio. Come out to listen to Charlie Anne on July 16th from 3-5pm.
Find out more »Live Music with Gary the Band
They're back!! Live Music with Gary the Band will be at Timber Hill Winery from 2-4pm! Formed in 2012, Gary the band brings a unique sound to the Southern Wisconsin area, basing their approach on vocal harmonies and tasteful guitar work. With all members of the band sharing the duties of vocals, guitar, and percussion, Gary the Band is able to play a diverse selection of music including classic and modern Pop, Rock, Folk and more. Combining individual studio albums…
Find out more »Live Music with Tim O’Grady
Join us on our patio for Live Music and enjoy a glass (or bottle) and snacks or dinner while you enjoy Live Music with Tim O'Grady! Tim is a local musician that covers country music. Check out more about Tim and where he will be by visiting his website or Facebook!
Find out more »Live Music with Andy Braun at Timber Hill Winery
Live Music with Andy Braun at Timber Hill Winery! Any Braun performs crowd favorites from the 50s on up! Artists such as Johnny Cash, The Beatles, CCR, Neil Young, Jimmy Buffett, and more! We are excited to have Andy back at the winery with Live Music from 2-4pm. For more info, visit andybraun.com
Find out more »Live Music with Jackie Ernst
Live Music with Jackie Ernst is at Timber Hill on July 31st from 2-4pm! Jackie Ernst is a Best of Madison singer/songwriter based in Southeastern Wisconsin. She is an emotive folk/rock artist with a bright powerful voice, and is sure to draw you in with her dynamic, edgy presence. Jackie’s sound has been compared to artists such as Stevie Nicks, Sheryl Crow, Alanis Morissette, Melissa Etheridge and P!nk. Bringing an eclectic mix of rock, pop, soul, country, folk & blues…
Find out more »August 2022
Live Music with Cyndi Meyer
Local musician Cyndi Meyer will be singing all your favorites! Join us for live music from 2-4pm! Cyndi has an amazing voice and you may recognize her from her band The Rainbow Bridge. She puts on a great show and we love having her! You can't go wrong with music and wine! Stop by Sunday, August 7th to catch Live Music with Cyndi Meyer at the winery!
Find out more »Live Music with Tim O’Grady
Join us on our patio for Live Music and enjoy a glass (or bottle) and snacks or dinner while you enjoy Live Music with Tim O'Grady! Tim is a local musician that covers country music. Check out more about Tim and where he will be by visiting his website or Facebook!
Find out more »Live Music with Jackie Ernst
Live Music with Jackie Ernst is at Timber Hill on August 21st from 2-4pm! Jackie Ernst is a Best of Madison singer/songwriter based in Southeastern Wisconsin. She is an emotive folk/rock artist with a bright powerful voice, and is sure to draw you in with her dynamic, edgy presence. Jackie’s sound has been compared to artists such as Stevie Nicks, Sheryl Crow, Alanis Morissette, Melissa Etheridge and P!nk. Bringing an eclectic mix of rock, pop, soul, country, folk & blues…
Find out more »Back2Back Live Music Acoustic Duo
Join us for Live Music with Back2Back Acoustics as Jim O’Connor & Christine Anderson will be at Timber Hill on Saturday, August 27 from 3-5pm! Back2Back covers a wide variety of artists and musical styles including rock, folk-rock, pop and a bit of country. You’ll hear songs by The Beatles, Michael Jackson, James Taylor, The Civil Wars, Fleetwood Mac, and more. They use a wide range of instruments including the following: Acoustic Guitar, Resonator Guitar, Square Neck Dobro, Ukulele, Keyboard,…
Find out more »Live Music with Jenna Lynne
Come enjoy Live Music with Jenna Lynne! She does everything from the Beatles to Taylor Swift. She also won Waukesha Idol, twice!! She is an up and coming artist who does everything from the Beatles to Taylor Swift. She also won Waukesha Idol, twice! You won't want to miss out! She will be on our patio from 2-4pm!
Find out more »September 2022
Live Music with Charlie Anne
Charlie Anne will be here with Live Music on the patio from 2-4pm! Charlie Anne is a duo who met through their love of music. They play a range of music that is perfect for sipping wine on the patio. Come out to listen to Charlie Anne on September 4th from 2-4pm.
Find out more »Live Music with Cyndi Meyer
Local musician Cyndi Meyer will be singing all your favorites! Join us for live music from 2-4pm! Cyndi has an amazing voice and you may recognize her from her band The Rainbow Bridge. She puts on a great show and we love having her! You can't go wrong with music and wine! Stop by Sunday, September 11th to catch Live Music with Cyndi Meyer at the winery!
Find out more »Live Music with Andy Braun at Timber Hill Winery
Live Music with Andy Braun at Timber Hill Winery! Any Braun performs crowd favorites from the 50s on up! Artists such as Johnny Cash, The Beatles, CCR, Neil Young, Jimmy Buffett, and more! We are excited to have Andy back at the winery with Live Music from 2-4pm. For more info, visit andybraun.com
Find out more »Live Music with Dan Brusky
Live Music with Dan Brusky is back on September 18th from 2-4pm! Local guitarist and vocalist, Dan Brusky, has been entertaining audiences for over 20 years. His unique interpretations of songs by such artists as Foo Fighters, Eagles, Stone Temple Pilots, Darius Rucker (Hootie), Doobie Brothers, Maroon 5, Zac Brown Band, Johnny Cash, Michael Jackson, and many others, is sure to keep you entertained. Dan will be here from 2-4pm, so come hangout on the patio for an afternoon of…
Find out more »Back2Back Live Music Acoustic Duo
Join us for Live Music with Back2Back Acoustics as Jim O’Connor & Christine Anderson will be at Timber Hill on Sunday, September 25th from 2-4pm! Back2Back covers a wide variety of artists and musical styles including rock, folk-rock, pop and a bit of country. You’ll hear songs by The Beatles, Michael Jackson, James Taylor, The Civil Wars, Fleetwood Mac, and more. They use a wide range of instruments including the following: Acoustic Guitar, Resonator Guitar, Square Neck Dobro, Ukulele, Keyboard,…
Find out more »If you are looking for an event that is not listed on our calendar or have questions please send us an email at events@timberhillwinery.com.