
Sometimes, all we need is a weekend getaway—a few days to leisurely wander through a vineyard while enjoying a cool glass of wine, preferably a country club pour.
If you live in Chicago like we do, finding vineyards can be quite a challenge, mostly because they are so sparse. When we think of wine country, most of us envision regions in California, specifically the northern San Francisco Bay Area.

But who was the money to buy a plane ticket to Napa in this economy? We see you, Napa, and we say no thank you—especially when there’s a charming wine town everyone is raving about within driving distance of Chicago. In fact, Travel + Leisure recently named Hermann, Missouri, as one of the best small towns for summer vacation in the U.S.
Hermann is often referred to as the crown jewel of the Missouri River Valley. The scenic town is known for its picturesque German architecture and vineyards, making it a quintessential summer vacation stop. Founded in 1837 by German immigrants, Hermann is located in the heart of Missouri’s wine country and is home to approximately 2,400 residents.
Getting to Hermann takes roughly 5 – 5.5 hours by car, depending on traffic. Alternatively, you can also take trains and buses that provide transportation from Chicago. Below, you’ll find some features of the town recommended by Secret Chicago and the Travel + Leisure team.

What To do in Hermann, Missouri
- Deutschheim State Historic Site: Offers a guided tour of two beautifully preserved homes. View here
- Hermann Farm: Features a grand tram tour that includes a guided experience to the 1847 Teubner-Husmann home. View here
Local wineries in Hermann, Missouri
- Stone Hill Winery: Missouri’s largest grape grower has 192 acres of vineyards that span seven sites surrounding the Hermann area. View here
- Adam Puchta Winery: They offer the Heritage Tasting, which is a guided wine journey with a trained wine steward, featuring Puchta family wines from their 7th-generation, family-owned winery. View here

Where To Stay in Hermann, Missouri
- The Cottage: Stay in one of the property’s three tree houses, nestled among the region’s rolling hills and offering stunning views of the lush landscape. View here
- The Inn at Hermannhof: A romantic inn that Jane Austen would have loved. Each room at the Inn is quipped with luxurious bathrooms featuring whirlpool tubs for two and oversized showers, along with fireplaces in the bedroom and bathroom. View here