Day One: Wined and Dined in Augusta

The ambling pace of wine country is far from the bustling spirit of St. Louis, but your first stop, Augusta, is just an hour's drive along State 94. Filled with quaint B&Bs, this town also boasts several wineries and a beer garden.

The aptly named Mount Pleasant Winery sits on a rise overlooking vibrant fields. Choose your vintage, buy cheese and crackers from the deli, and have a picnic in a little gazebo with a big view. Enjoy equally stunning vistas at Montelle Winery, where deli sandwiches and Missouri-made salami taste even better on a shady deck on a 400-foot ridge above the valley. On some Friday evenings, Sugar Creek Winery in nearby Defiance has live music.

Hop on the Katy Trail near the Augusta Brewing Co. The outdoor beer garden promises beer brats, beer, and Missouri wine at the end of your jaunt. Spend the night at the H.S. Clay House, a rare B&B with a pool and a hot tub. We loved the gourmet breakfast and the treetop suite, which feels like a secret hideaway.