TL;DR: Things to Do at Timber Hill Winery (Milton, WI)
Looking for things to do in Milton, WI? Timber Hill Winery offers:
Wine tastings at the bar (no reservation needed)
Behind the Vines guided wine tastings (reservation required)
Wineo Bingo every other Friday supporting local nonprofits
Friday Night Trivia every other Friday with rotating themes
Live music every Sunday
Whether you’re planning a date night, casual outing, or girls day, there’s always something happening at Timber Hill Winery.
The Complete Guide: Things to Do at Timber Hill Winery (Milton, WI)
Looking for things to do in Milton, WI? Planning a date night near Janesville? Visiting southern Wisconsin and want a winery experience that offers more than just a tasting?
Welcome to your complete guide to weekly events, wine tastings, and experiences at Timber Hill Winery.
Whether you’re stopping in for a casual glass, booking a guided tasting, or joining us for Friday night fun, there’s always something happening here.
🍷 Wine Tasting at the Bar
If you’re new to Timber Hill or simply looking for a relaxed outing, start with a wine tasting at the bar.
Guests can build their own tasting flight and explore a range of wines—from dry reds and crisp whites to fruit-forward favorites and seasonal specialties. Our team is always available to help guide you toward something you’ll love.
Best for:
First-time visitors
Casual afternoons
Easy, spontaneous date nights
Out-of-town guests exploring Wisconsin wineries
No reservation required—just stop in and sip.
🍇 Behind the Vines Guided Wine Tasting (Reservation Required)
For a more immersive experience, book Behind the Vines, our 45-minute guided wine tasting.
This elevated tasting includes:
Four curated wine samples
A charcuterie cone pairing
Guided education from a wine expert
An inside look at the Timber Hill story
This experience takes place in The Den and is reservation-only. It’s ideal for guests who want to go beyond the pour and understand what makes each wine unique.
Perfect for:
Date nights
Small group outings
Celebrations
Guests searching for guided wine tastings in Wisconsin
Available on the first Saturday of each month (excluding March and May. Behind the Vines will be available March 14th and May 16th during these months). Book now!
🎟️ Wineo Bingo (Every Other Friday)
Every other Friday night, Timber Hill hosts Wineo Bingo, one of our most-loved community events.
Wineo Bingo proudly supports local nonprofits and community causes throughout Milton, Janesville, and surrounding southern Wisconsin communities.
Each event helps spotlight and give back to organizations making a difference locally. When you attend, you’re not just enjoying a night out—you’re helping support meaningful causes in our area.
Expect:
A lively tasting room
Fun prizes
A welcoming, high-energy atmosphere
A feel-good Friday night experience
If you’re searching for Friday night events in Milton, WI that give back to the community, Wineo Bingo is a must.
🧠 Friday Night Trivia (Every Other Friday – Alternates with Bingo)
On the Fridays we’re not hosting Wineo Bingo, we host Friday Night Trivia.
Trivia takes place every other Friday and features a new theme each week—from blockbuster hits like Mean Girls and Harry Potter, to beloved TV shows like Gilmore Girls and The Office. Check our events calendar for the next themes!
It’s free to play, casual, and always competitive (in the best way). Grab your team, order a bottle or tasting flight, and settle in for a night of laughs and friendly rivalry.
Because Trivia and Wineo Bingo alternate Fridays, there’s always something happening to kick off your weekend at Timber Hill.
🎶 Sunday Live Music
Wrap up your weekend with live music every Sunday at Timber Hill Winery.
Local musicians bring the patio to life while guests enjoy wine, food, and a relaxed, welcoming atmosphere. It’s one of our favorite ways to support local talent while bringing the community together.
Pair your glass with lunch, split a pizza, or simply unwind with friends and family.
Perfect for:
Sunday Funday plans
Visitors exploring Wisconsin wineries
Laid-back afternoons with great wine and music
More Than a Winery — A Community Gathering Place
At Timber Hill Winery, wine is just the beginning.
Our weekly events and private experiences are designed to create connection—between friends, families, neighbors, and local organizations. Whether you’re attending Wineo Bingo to support a nonprofit, competing in trivia, booking a guided tasting, or relaxing to live music, you’re part of something bigger.
If you’re looking for:
Things to do in Milton, WI
Winery events near Janesville
Guided wine tastings in southern Wisconsin
Live music at a winery
Friday night events that support local nonprofits
You’ll find it here.
Plan Your Visit to Timber Hill Winery
Located in Milton, Wisconsin, Timber Hill Winery is a destination for wine lovers, weekend explorers, and anyone looking for a welcoming place to gather.
Stop in for a tasting at the bar, reserve a Behind the Vines experience, join us for Trivia or Wineo Bingo, host a private event, or relax on Sunday with live music.
There’s always something happening—and there’s always a seat waiting for you. 🍷
Key Takeaways: Why Visit Timber Hill Winery?
It’s More Than a Winery
Timber Hill offers wine tastings, guided experiences, weekly events, live music, and private event space—all in one location in Milton, Wisconsin.
There’s Always Something Happening
With Wineo Bingo and Trivia alternating every Friday and live music every Sunday, your weekend plans are covered year-round.
Wineo Bingo Gives Back
Every other Friday, Wineo Bingo supports local nonprofits and community causes throughout Milton, Janesville, and southern Wisconsin.
You Can Elevate Your Experience
Book Behind the Vines for a guided, educational tasting that includes curated wines and charcuterie pairings.