Fall Wine Walk

Get ready to sip, stroll, shop, and savor at Sheboygan’s Fall Wine Walk on Saturday, October 24, 2026!

Explore the Downtown, Riverfront, and South Pier districts as local businesses transform into cozy tasting rooms, serving a selection of sweet and dry wines, along with refreshing mocktails. Hop aboard the trolley for a relaxing ride throughout the event area, making it easy to explore all the stops along the way.

Your General Admission ticket includes a souvenir wine glass and lanyard, giving you everything you need for an afternoon of tasting, shopping, and discovering local businesses.

Sponsored by: Downtown 925, Relish Kitchen Store & The GameBoard

✨ NEW! VIP Wine Walk Package | $75/person

Looking to make your Wine Walk experience even more memorable? The new 2026 Harbor Centre Business District Fall Wine Walk VIP Package offers an elevated experience with exclusive perks, tastings, gifts, and more—all while including your General Admission ticket.

VIP Package Highlights:

• Dining & Drinks: $15 lunch voucher to Blue Harbor Resort plus a $10 Salon Sase’ gift card
• Premium Pour: Enjoy one full 6 oz. glass of wine of your choice at one participating location
• VIP Swag Bag: Take home a specially curated bag featuring a full bottle of wine and additional merchandise and surprises valued at $30–$60
• Wine & Cheese Pairing Experience: Enjoy a guided 30-minute wine and cheese pairing at Downtown 925, featuring at least three locally produced Wisconsin wines, each thoughtfully paired with complementary cheeses or chocolates. Learn about the wines and the art of pairing while enjoying a relaxed tasting experience in the heart of Downtown Sheboygan.
• General Admission Included: Your VIP Package includes your Fall Wine Walk admission.

Whether you choose General Admission or go VIP, this is the perfect way to gather your friends, discover local businesses, and enjoy an afternoon filled with great wine, delicious pairings, shopping, and fun throughout Harbor Centre.

Tickets go on sale September 24, 2026!

Sip. Stroll. Savor. We’ll see you at the Fall Wine Walk!