7 Fall Drives in and Around St. Louis

Go for the color, stay for the wine.

Kids in school, nip in the air, trees start to turn, and autumn is here. Seven drives in and around St. Louis offer plenty of fall color, plus wine, history, biking and more. 

Alton to Grafton

The gold standard for scenic drives in the St. Louis area takes you from Alton to Grafton, Illinois, along Highway 100 past spectacular limestone bluffs and the wide Mississippi River. Along the way you'll find the uber-charming village of Elsah, fishing and boating opportunities, antiques, wineries and dining. If you brought your bike, you can pedal along the river on the Sam Vadalabene Bike Trail.

Limestone bluffs between Alton and Grafton, Illinois

Highway 100 to Hermann

This is also known as the Hermann Wine Trail, since Highway 100 west of St. Louis passes by some seven wineries, including Röbller, Bias, OakGlenn and Stone Hill, on the way to and in the picturesque town of Hermann, Missouri. Recommended for lunch: Harvest Table, where you'll find lots of local food and beverage products. Check out the Deutscheim State Historic Site and the Historic Hermann Museum, then shop the day away in the walkable business district.

Hermann, Missouri

Highway 94 Wine Country

Highway 94 from Highway 40 to Dutzow owns the lion's share of wineries in the St. Louis region, and the serpentine road absolutely demands a designated driver. Some of our favorites: Montelle Winery (best view), Augusta Winery and Mount Pleasant Estates (both in Augusta), Noboleis Vineyard (relatively new turning out award-winning wines) and Blumenhoff Vineyards (music on weekends). The wine ranges from good to great...really great. You can also stop in at the Daniel Boone Home & Heritage Center in Defiance and try to solve the mystery of where Daniel is buried. The Katy Trail follows Highway 94 along the Missouri River, and there are bike rentals in St. Charles and Defiance.

Montelle Winery

Ste. Genevieve

Take I-55 (not that scenic) down to Ste. Genevieve. Once you're off the interstate, the scenery gets better, the history gets interesting, and the wine gets superb. Downtown Ste. Genevieve still maintains a clutch of historic buildings that date back to French colonial days and serve as a springboard for history lessons about Missouri's earliest European community. Wineries dot the hills west of the town, including the extraordinary Chaumette Winery, complete with tasting room, restaurant, spa, villas and the best norton we've ever tasted.

Chaumette Winery

St. Louis to Prairie du Rocher

A trip from St. Louis to Prairie du Rocher takes you through very picturesque Illinois countryside down Highway 3 to Waterloo, Highway 7 to the historically German village of Maeystown, and down Bluff Rd. to Prairie du Rocher, founded in 1722 as the fourth European settlement in Illinois. Nearby Fort de Chartres (c. 1754) is operated as a State Historic Site.


The quaint little river town of Kimmswick rewards visitors with fun shopping (antiques, crafts, decorative accessories, gifts, Christmas, pottery and more) and the famous Blue Owl Restaurant & Bakery, renowned for its extravagant desserts.

David Lancaster
About the author

David Lancaster has been editor of Where St. Louis...