Posted on October 7, 2026
Across Southern Wisconsin, the exploration of authentic wines opens the region's visitors to an understanding of the state through its finer moments. Each year of wine carries distinct regional characteristics that are more than just flavor or aroma, each holding a note of Wisconsin in each sip. In their variety, there is much to discover about this region's wines in one weekend, so, with this quick jaunt across Southern Wisconsin, come and join us for this Wine Weekend with its unforgettable stops!
Stop 1 - Wine - Staller Estate Winery & Distillery
For our first stop, we have Staller Estate Winery & Distillery, a family-run winery situated just north of Delavan, WI with internationally recognized vineyard and winemaking curation! Their stock of dry red and dessert wines make for a sharp variety especially when paired with their tasting hors d'oeuvres menu. This establishment is dedicated to great amateur wine but, more than that, they know the importance of leisure in tasting that vineyard estates can sometimes feel they lack which they make up for in their quiet country atmosphere. With options of educational connoisseur tours and private tasting experiences available, be sure to reserve a spot ahead of time and make the most of your time at Staller Estate Winery & Distillery.
Stop 2 - Dinner - 1878 on the Lake
With a full day out and about Delavan behind you, you are sure to be wanting for a nice sit-down dinner. What better way is there to dine than with a signature lakefront experience at 1878 on the Lake? The fine dining setting with its selection of local and cuisine dishes, whether you are craving some lakefront catches or something casual but fancy, makes for the perfect close to a perfect day. Late night dining experiences are best served with a nice glass of your preferred vintage, making their bar services with local options invaluable. Take in the sunset in style and at 1878 on the Lake at Lake Lawn Resort.
Stop 3 - Unique Stay - Lake Lawn Resort
And when you're considering where to settle for the night, the exceptional convenience and comfort of Lake Lawn Resort is the best option around! Its homely campus is host to plenty of lakeside accommodations, weekly family-friendly activities, and opportunities to enjoy the season throughout the resort's forested space. As one of Wisconsin's historical resorts, there is an undeniable appeal to a space that has proven its abilities to satisfy its patrons over nearly 150 years of operations. Whether for a pair or for a larger ground, Lake Lawn Resort has much to offer and much more to discover regardless of preference for accommodations or recreation.
Stop 4 - Food, Music, & Wine - Bailey's Run Vineyard & Winery
As we head west towards New Glarus and Madison on our second day, we find ourselves at Bailey's Run Vineyard & Winery, and it does not disappoint! Situated west of New Glarus, this winery offers daily a vast range of wines and serves with a deep understanding of what different palettes may desire out of a tasting. Regular live music and holiday events and reserved wine tasting flights alongside an impressive small plates and pizzeria menu make even the non-winery offerings quite appealing to any sort of visitor! Both as a place to spend the day and enjoy company, taking your time with this stop at Bailey's Run Vineyard & Winery is worthwhile, especially for groups.
Stop 5 - Unique Stay - The Edgewater
After a long day of travel within the region, finding yourself in the state capital of Madison, WI feels inevitable with the draw towards its beautiful architecture and impressive culture. When you're in town, booking an evening at The Edgewater in the heart of Downtown Madison is a great choice! With its central location and variety of suites on the waterfront, there is an appeal to be found for the traveling tourist who enjoys exploring their surroundings! Luxury and in-house services make this hotel one of the best in the region by far! The Edgewater is certainly hard to beat!
Stop 6 - Lunch & Wine - Wollersheim Winery & Distillery
For our final stop, we head northwest to the Wisconsin River and the village of Prairie de Sac, WI for a perfect lunch and wine at the Wollersheim Winery & Distillery! With nearly 200 years of experience, this property features among the highest awarded wineries in the state with generations of wisdom from its winemakers and disillers. On its hillside, you can enjoy a guided walking tour through its vineyards and cellars or take up one of its regular Wine by Design Tasting with unbeatable offerings across its wine options. For aromas and tastes unlike any others, check out Wollersheim Winery & Distillery as a close to this Southern Wisconsin Wine Weekend.