Name: Downtown Middleton Sip & Stroll
Start: 2026-04-30T17:00:00-05:00
End: 2026-04-30T20:30:00-05:00
Location: Downtown Middleton

Downtown Middleton Sip & Stroll

WHEN:
April 30, 2026 @ 5:00 pm - 8:30 pm

ADMISSION: $12 – $40

WHERE:

Downtown Middleton

Middleton,WI 53562

Website

This event has passed.

This contains details from 2026 Sip & Stroll. Stay tuned for information on 2027 Sip & Stroll.

Raise your glasses and grab your passports! The Downtown Middleton Business Association is excited to host our annual Sip & Stroll: Wine Walk. This year the theme is Around the World!

This event is organized by the Downtown Middleton Business Association and will take place from 5 – 8:30 p.m., Thursday, April 30. Each of the 17+ stops along the way will feature a wine from a different region of the world, giving you the chance to explore international flavors as you stroll through the historic Downtown Middleton. Whether you’re a seasoned connoisseur or simply enjoy a cold drink, this event promises something for everyone.

This Sip & Stroll isn’t just about drinking — it’s also a celebration of community and culture. As you stroll from one tasting station to the next, you’ll have the opportunity to discover the unique flavors and personalities of Downtown Middleton’s vibrant local businesses.

How it Works

Participants must be 21 or older and present an ID to receive a wristband. Once they've picked up a wristband, glass and ticket, attendees can choose their own path along the walk, selecting which stops to visit from 5 - 8:30 p.m. Each stop will offer delicious food and a selection of wines to sample. It’s a personalized experience to enjoy to the fullest!

Tickets

Includes:

17+ sip stops
Keepsake sampling wine glass
Delicious apps and snacks at each stop
Photo op stops along the way
Exclusive specials from participating businesses

Pricing

Sip & Stroll tickets cost $40 per person, or participants can enjoy all the food and entertainment with a $12 designated driver ticket.

Purchase Tickets Here

Photos

In a charming mustard shop, during the Downtown Middleton Wine Walk, two women enjoy the moment: one pours a drink while the other holds a cup. Behind them, shelves filled with mustard jars surround a large pretzel decoration, adding to the cozy ambiance of the Sip & Stroll event.

A woman in a black apron holds a wooden tray of pastries inside a Downtown Middleton shop. Various items are displayed on shelves behind her, ready for you to explore during the lively Sip & Stroll event.

A woman behind a retail counter hands a drink to a customer during Downtown Middleton’s Sip & Stroll, while another customer waits in line at the boutique-style store.

Four women stand indoors, holding drinks and smiling, embodying the spirit of a Sip & Stroll. They wear casual attire and lanyards with name tags. Behind them are shelves of products and a sign for BBQ sauces, capturing the vibrant essence of Downtown Middleton.

Five people smiling and holding humorous signs about wine inside a building with a dark wall, part of the lively Sip & Stroll event in Downtown Middleton.

Two people are smiling, wearing matching "Wine a little, Laugh a lot" shirts. They hold wine glasses during the Wine Walk event in Downtown Middleton. The scene is set in a store with colorful baskets and cards adding to the festive atmosphere.

Lodging

Experience the fun of Sip & Stroll while staying conveniently nearby. Kick off the weekend early and book a stay at one of Middleton's nine hotels, all just five minutes or less from Downtown Middleton. For a prime location, consider Staybridge Suites, situated right in the heart of downtown.