- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
Fall in Western Wisconsin is pure magic—and local wineries are the perfect place to slow down and take it all in. Whether you’re sipping mulled wine on a patio, sampling apple-forward blends, or just watching the leaves fall across the vines, these five wineries offer seasonal specials that make autumn even sweeter.
Fall Highlight: Mulled Wine by the Glass + Pumpkin Cheesecake Pairings
Styled like an Italian villa, this winery goes all-out in the fall. Sip warm mulled wine on the piazza while enjoying vineyard views wrapped in gold and orange. Their seasonal dessert pairings are a favorite, especially the pumpkin cheesecake with a late harvest white.
Bonus: Located in charming Pepin—pair your visit with a stroll by Lake Pepin.
Fall Highlight: Hot Spiced Wine + Harvest Dinner Events
This open-air winery tucked in the Rush River Valley is a fall bucket-list stop. Their famous hot spiced wine is served piping hot under string lights with fire pits nearby. Weekends often feature live music and multi-course harvest dinners with wine pairings.
Bonus: Surrounded by wooded bluffs, it’s one of the most scenic places to drink wine in fall.
Fall Highlight: Sogn Blush Fall Sangria + Autumn Vineyard Tours
Okay, it’s technically across the river in Minnesota—but Cannon River Winery’s seasonal sangria, made with local apples and cinnamon spice, is a must-try. Their guided vineyard tours continue through early October, and the foliage is absolutely worth the detour.
Bonus: The tasting room is located in a restored 1908 building filled with charm.
Fall Highlight: Free Fall Tastings + Orchard Views
This blufftop winery offers free tastings year-round, but the fall experience is extra special. Their Frontenac blends and apple-kissed whites are ideal for cool-weather sipping. Bring a blanket and enjoy a picnic on the hillside with views of both vineyard and orchard.
Bonus: Grab a bottle and hike the nearby Eagle Bluff trail after your tasting.
Fall Highlight: Wood-Fired Pizza + Autumn Wine Flight
A laid-back, family-owned winery just across the border with cozy fall touches—think wine flights featuring dry reds, apple blends, and their fall-favorite Marquette. Pair it with their seasonal pizza specials on the deck overlooking the vines.
Bonus: Their on-site bistro stays open through October weekends.
There’s no better way to celebrate the season than with good wine, warm company, and autumn views. Make it a getaway with local hiking, antique shopping, and a stay at one of our boutique hotels nearby.
🍷 Plan your wine weekend now → Browse our fall-ready stays in Prescott
Make downtown Prescott your home base and book direct with us: The Port of Prescott for boutique king suites steps from the river, Port After Dark for romantic suites made for couples, The Harbor Hotel for themed rooms and extended stays, and The Cove Guest House for downtown condos and group getaways.
