Gear Up for Grapes
Start your drive in Augusta (50 miles west of St. Louis), where you'll find nine wineries within a 15-mile radius. The oldest, Montelle (montelle.com), is famous for its views, while the newest, Noboleis Vineyards (noboleisvineyards.com), is revered for its laid-back vibe (lawn games!).
Say Gute Nacht!
Check in at New Haven's Cedar Creek (visitcedarcreek.com; rooms from $152). The former corporate retreat center opened to the public last year with a 37-room lodge and three cozy homes set on 200 acres. Book two nights for time to revel in Hermann's Oktoberfest.
Brake for Bratwurst
Founded by German immigrants, the town of Hermann still hosts Oktoberfest—a citywide devotion to the area's roots complete with polka bands, beer, wine, and brats—every weekend in October. Track down reputed sausage-maker Michael Sloan at the Hermann Wurst Haus (hermannwursthaus.com).
Veer Toward Vintage
Hit the road for Rocheport, skipping the highway and driving about 90 miles alongside the Katy Trail for views of riverbank towns. In Rocheport, order a brick-oven pizza ($5 and up) at Mulberry Grill & Bakery (660/728-3667). Then troll antiques shops along Central Street.
Pick a Pumpkin
Head toward Glasgow, but squeeze in a detour to Boonville, roughly 12 miles up the road, for a hayride ($5) at Arnett's Peach Tree Farm (thepeachfarm.com). Don't let the name fool you: This stop has the area's most bountiful pumpkin patch.
Raise a Glass
In historic Glasgow, indulge in a slice of pie at the Rolling Pin (660/338-0800). Walk around the quaint downtown before settling in at Bushwhacker Bend Winery (bushwhackerbend.com). Order a glass of the Chambourcin ($5) and snag a table on the deck to watch the sunlight dim across the river—a perfect amber ale-like glow. Prost!