Hermann was incorporated in the 1830s after its 11,000 acres of land were divided and purchased virtually sight unseen by a German settlement society in Pennsylvania. Their goal: to build a new town in the American West that would replicate a traditional German riverside village, similar to those in the Rhine Valley. The area’s steep, rocky terrain proved challenging, but Hermann’s pioneering settlers made an agricultural investment that would seal the town’s fate: vineyards. Within just a few decades, Hermann boasted the second-largest winery in the nation. With Prohibition, Hermann became all but a ghost town. But with the revival of its vineyards in the 1960s, this town of 2,500 people is once again known for its wine, as well as the gorgeous landscape that bears the fruits of its labor. Coupled with stunning valley views, lively festivals, and 19th-century architecture, Hermann is an old-world destination revived for modern getaways.

Hermann has something to offer you in all four seasons, though its warm-weather festivals are added incentives to book a visit. With deeply rooted German heritage, it’s no surprise that the town’s biggest festivals follow German traditions. Maifest takes place the third weekend in May, when greenery and flowers bring the town to life; and Oktoberfest is spread over four weekends in October, when the valley bursts with autumn color. Other ideal times to book one of the area’s cabins are during Wurstfest in mid-March, helping to seal Hermann as the sausage-making capital of Missouri; and the Rhythm and Brews festival, held annually in June. While Hermann’s half-dozen wineries are open year-round, fall is perhaps the most beautiful time to explore the wine valley.

Wine Trail

You’d be remiss to visit Hermann without taking a drive along its beautiful wine trail. Spanning 20 miles, the trail connects seven family-owned wineries between Hermann and New Haven. Wineries are open year-round for tastings and tours, and several events throughout the year offer opportunities to explore them in detail.

Katy Trail State Park

Stretching 240 miles across the state of Missouri, the Katy Trail is the longest recreational rails-to-trails project in the United States. Hermann marks a significant spot: the 100-mile marker on the trail (with a presumed start in the east). With picturesque bridges, scenic outlooks, and even a few major cities in its path, it’s a lovely way to explore beyond Hermann’s town limits.

Hermann Farm Museum

Perched on the northeast edge of town, the Hermann Farm dates from the 1840s, and has preserved many of its iterations along the way. Its current owners, whose family has managed the farm for more than a century, maintain the buildings as a replica of a typical 1850s Missouri farm.