The Missouri Rhineland winds through the Missouri River Valley from the suburbs of St. Louis to Jefferson City. This region is called “wine country” due to the soils that line the southern bank of the river. The soils are excellent for growing wine, grapes, and (of course) corn. The Rhineland was named for its similarities to the Rhineland region in Europe. Some of the oldest wineries in America were founded here, especially near Augusta and in Hermann at Stone Hill. During Oktoberfest, you’ll find towns that still celebrate their German heritage in style.
This tour will take you through Missouri wine country to see the industry that has won multiple national awards. Even if you are not a fan of wine, it’s still a beautiful area with rolling hills, vineyards, and rich earth. The German heritage is also seen in its architecture that that still stand over 150 years later.
How long? About 123 miles or a minimum of three hours. The hills are steep, and the roads are usually two-lanes with speed limits of 35 m.p.h. at times. Best advice? Slow down. You’ll also find tiny little “German villages” on the route to explore. The bridge on Highway 94 in Hermann is under construction so you must take local road P as an alternate and it also goes through some great places, but the road is not one to be speeding on.
Add 30 minutes if you are leaving St. Louis to drive to St. Charles, Missouri.
If you are starting from the Kansas City metroplex, add an additional two hours and a half hour to drive to Jefferson City and reverse the directions. (Or, you can simply drive four hours to St. Charles and then start the tour.] Plan for a full day of driving.
Time of Year? The best times to visit are from April to November as the roads can get dangerous in the winter months. Check for any flash flood watches or warnings as some of the roads can be closed by heavy flooding. You will see signs everywhere warning about low water crossings.
Map not working on your phone? Try this one.
Missouri Rhineland / Wine Country Itinerary
Start from St. Louis, Missouri
Side-trip. If you are driving from St. Louis, Missouri, why not stop off in Florissant, Missouri, to view the oldest church in Missouri. Old St Ferdinand Shrine at 1 Rue St Francois, Florissant, MO 63031. The parish was established in 1789 and the original part of the church was built in 1821.
230 S. Main Street, St. Charles, MO 63301
Mother-in-Law House, built in 1866 in St. Charles, Missouri.
First Missouri State Capitol Building in St. Charles.
Flower outside of the Mother-in-Law House in St. Charles
St. Charles, Missouri, was once the last outpost for westward-bound pioneers and where Lewis and Clark launched their expedition to the Pacific. French-Canadian settlers called the spot Les Petites Cotes after “the little hills” in the 1700s. Settlement of the city dates to 1769. The city also served as the nation’s first state capitol. Little Hills Winery in historic St. Charles used to operate in a building erected in 1805. It is the first recorded deed on file and was one year after Lewis and Clark arrived in the area. Unfortunately, the shop closed in early 2018, but it is still interesting to see one of the oldest structures in the region. The historic downtown district also has shopping, restored historic structures, and other sites to help you get into the mindset to go back in time through the Rhineland of Missouri.
Since no wineries are left in downtown St. Charles, drive up and down Main Street to view some of the oldest parts of the city.
- First Missouri State Capitol State Historic Site, 200 S Main St, St Charles, MO 63301
- Mother In Law House, 500 S Main, St. Charles, Mo 63301
[Old Little Hills Winery Building, 501 S Main St, is across the street]
- Lewis & Clark Boat House and Museum, 1050 S. Riverside Dr., Saint Charles, MO 63301
- Frenchtown Heritage Museum, 1121 N 2nd St, St Charles, MO 63301
- Charles Borromeo Catholic Parish, 601 N 4th St, St Charles, MO 63301
- Nathan Boone Homestead State Historic Site, 7850 N, 8159, State Hwy V, Ash Grove, MO 65604
Chandler Hill Vineyards, 596 Defiance Rd, Defiance, MO 63341
The history of Defiance, Missouri, goes back to 1804 with explorer Meriwether Lewis and William Clark and Daniel Boone. The Daniel Boone Home, a four-story, Georgian-style home, can still be explored today. In addition to a long history, four wineries also operate within a two-mile radius and nearly a dozen more wineries operate over the next 15-miles on the way to Dutzow. This area, that goes to Augusta, Missouri, is the oldest wine district in the United States. Chandler Hill Vineyards is a young winery, operating since 2008, but it has some of the most picturesque views of the region.
Additional wineries in this area include:
- Sugar Creek Winery, 125 Boone Country Ln, Defiance, MO 63341
- Defiance Ridge Vineyards, 2711 S Missouri 94, Defiance, MO 63341
- Holy Grail Winery (wine and chocolate), 17814 State Hwy N, Marthasville, MO 63357
- Historic Daniel Boone Home (not a winery, but still cool), 1868 Hwy F, Defiance, MO 63341

5634 High St, Augusta, MO 63332
When Germany immigrants flooded the area back in the 1800s, they brought with them their love of flowers, Teutonic architecture, and their wine-making skills. Eleven wineries operated near Augusta until the Prohibition era when they were closed. Time moved on and many of the wineries reopened. The area outside of Augusta was designated as the first American Viticultural Area (wine growing) in 1980. Brothers George and Frederick Muench founded the winery in 1859 and built the cellars in 1881. The winery still uses the cellars today to age the wines and Augusta Ports.
Additional wineries include:
- Montelle Winery, 201 Montelle Dr, Augusta, MO 63332
- Noboleis Vineyards, 100 Hemsath Rd, Augusta, MO 63332
- Augusta Winery, 5601 High St, Augusta, MO 63332
- Cedar Lake Cellars, 11008 Schreckengast Rd, Wright City, MO 63390
13699 South Highway 94, Dutzow, MO 6334
Dutzow is Missouri’s oldest Germany settlement, founded in 1832. The vineyards at Bluemnhof were established in 1979 with the first vintage in 1986. Blumenhof, which means “Court of Flowers” in German,” has won a wide variety of awards at prominent wine competitions. Near the old town of Pinckney on MO-94 is St. John’s United Church of Christ that was built in 1870 and is one of the few remaining structures in the area that survived the floodwaters of 1993.

123 Lafayette St, Washington, MO 63090
In the middle of Missouri wine country sits Washington, Missouri, a charming small town on the Missouri River. The town was the site of the San Juan del Misuri, established in 1796. The renamed town was plotted out in 1829. Thanks to the influx of anti-slavery Germany settlers, Washington, Missouri was a union holdout in a state that supported the Confederacy during the Civil War. There are over 40 wineries within an hour of the town, but since we’ve already explored so many, I figured it was time for a history break. Here are a few of the historical sites to see in this old German settlement.
- The Farmhouse at the Kohmueller Farmstead, Kohmueller Farmstead, Washington, MO 63090
- Historical Society Museum, 113 E 4th St, Washington, MO 63090
- Fort Charrette Historic Village and Museum (the 1790s), 966 Charrette Lane, Washington, MO 63090
- John’s African Methodist Episcopal Church (AME), Walnut St & E 4th St, Washington, MO 63090
- Bacon Log Cabin, 687 Henry Ave, Ballwin, MO 63011
1110 Stone Hill Hwy, Hermann, MO 65041

Hermann, Missouri, is one of the state’s hidden gems. Founded in 1837 by German immigrants, Hermann, Missouri, is considered the heart of the Missouri Rhineland region. The town’s German-American heritage can be viewed at the Deutschheim State Historic Site and in its downtown. The Pommer-Gentner house was built in 1840 and the Carl Strehly house, built in 1842, are two of the oldest surviving buildings in town. Stop at the Hermann Riverfront (free parking!) for a great view of the Missouri River. Hermann is a great weekend get-away in and of itself.
The oldest winery in Hermann is Stone Hill Winery, established in 1847. Norton, Missouri’s official state grape, is grown here. The winery has won more than 4,000 awards since 1988. Stone Hill Winery offers guided tours and tasking, along with a vintage restaurant that specializes in German and American cuisine.
Black Shire Distillery in Hermann, Missouri.
Courthouse in Hermann, Missouri
Shops in downtown Hermann offer a variety of American and German offerings.
Another view of Downtown Hermann, Missouri
Founded in 1886, the Inn at Hermannhof is in downtown Hermann.
Hermann 1837 Bar at Hermann Crown Suites is a historical building in town
View the Missouri River down by the Hermann Riverfront. Free parking!
In addition to wine, Hermann also has a variety of distilleries and brewing companies.
Additional wineries include:
- Adam Puchta Winery, 1947 Frene Creek Rd, Hermann, MO 65041
- Hermannhof Vineyards, 330 E 1st St, Hermann, MO 65041
- Oak Glenn Vineyard and Winery, 1104 Oak Glenn Pl, Hermann, MO 65041
- Martin Brothers Winery, 1623 Old Iron Rd, Hermann, MO 65041
- Endless Summer Winery, 5 Grosse Ln, Hermann, MO 65041
1707 S Summit Dr, Holts Summit, MO 65043 (winery)
201 W Capitol Ave, Jefferson City, MO 65101 (capitol building)
View of the Missouri State Capitol walking up from the public parking lot.
View of some of the frescoes inside of the dome of the Missouri State Capitol Building.
View of some of the frescoes inside of the dome of the Missouri State Capitol Building.
The Missouri State Museum has exhibits inside of the Missouri State Capitol building that you can tour for free.
The French influence on the state of Missouri can be felt in many of the touches on the capitol building.
The first recorded mass in Jefferson City was in 1831. The current church was built in 1881.
St. Peter Catholic Church in Jefferson City, Missouri.
Lewis and Clark play a heavy role in traveling Missouri’s wine country.
As you near the capital of Missouri, you’ll see the northern edge of the Ozark Plateau and the southern part of the Missouri River. The capitol dome rises from a bluff overlooking the river in historic Jefferson City. Sitting on the western edge of Missouri wine country, the city has several wineries within a short drive.
Additional wineries and nearby places include:
- Serenity Valley Winery, 1888 County Rd 342, Fulton, MO
- Wenwood Farm Winery, 1132 Brick Church Rd, Bland, MO
- Hummingbird Vineyard & Winery, 16586 Audrain Road 953, Mexico, MO
- Les Bourgeois Vineyards, 14020 West Hwy Bb, Rocheport, MO
- Jefferson Landing Historic State Site, 100 Jefferson St, Jefferson City, MO 65101
- Missouri Supreme Court Building, 207 W High St, Jefferson City, MO 65101
- St Peter Church, 216 Broadway, Jefferson City, MO 65101
Have some spare time after visiting Jefferson City? Go south and explore the Missouri Ozark Country.

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