Meramec Caverns, Ha Ha Tonka Castle & Lake of the Ozarks

Missouri's longest commercial cave at 4.6 miles explored — open since 1935 after owner Lester Dill transformed it from a Civil War gunpowder depot into a tourist attraction. The 1-mile guided tour passes through seven chambers including the Wine Table (a flowstone formation 60 feet wide and 20 feet tall that looks like a tablecloth draped over a table), the Stage Curtain (the largest cave onyx formation in the world at 70 feet tall), and the Throne Room. Jesse James is said to have used the cave as a hideout after the 1876 Northfield, Minnesota bank robbery; the claim is disputed but adds to the cave's appeal. Constant 60°F temperature year-round.

Missouri's oldest winery and the second largest American winery before Prohibition closed it in 1920 — revived in 1965 in the original stone cellars. The seven arched vaulted rooms carved into the hillside are still used for aging; the winery produces Norton (Missouri's state grape) and Vignoles wines that regularly win national awards. Hermann was chosen by the German Settlement Society of Philadelphia in 1836 specifically for its Rhine-like topography — rolling hills, a river bend, and limestone soils favorable to viticulture.

Hermann's downtown historic district preserves 19th-century commercial blocks along Market and First streets — virtually unchanged because the town never grew large enough to justify demolition and replacement. The Deutschheim State Historic Site preserves two original German immigrant homesteads from the 1840s. The Missouri River bend below Hermann is visible from the bluffs above the winery district; the riverfront park provides a walking path with views of the limestone bluffs on the opposite bank.

A restored 1886 brick hotel on Market Street in downtown Hermann — walking distance from both Stone Hill and Hermannhof wineries. Tomorrow's drive to Ha Ha Tonka State Park is 90 minutes southwest through the Osage River Valley.

A European-style stone castle stands in atmospheric ruin on a 250-foot bluff overlooking the Lake of the Ozarks — built beginning in 1905 by Kansas City businessman Robert Snyder McClure as a private country estate, destroyed by fire in 1942 before it was ever completed. The roofless stone walls, tower, stables, and greenhouse ruins sit within a karst landscape of sinkholes, caves, and Ha Ha Tonka Spring — one of Missouri's largest springs, discharging 48 million gallons daily into a turquoise pool that flows directly into the lake. The castle ruins trail (0.5 miles) combined with the Spring Trail (2 miles round trip) gives the full Ha Ha Tonka experience.

The park's karst features beyond the castle ruins — a natural bridge (a collapsed cave ceiling that left a 70-foot rock arch spanning a sinkhole) and Colosseum Cave (a large cavern entrance visible from the trail, home to cave swallows in summer). The Devil's Kitchen (a deep sinkhole with collapsed walls creating a natural amphitheater) is accessible on a short side trail. Ha Ha Tonka in the Osage language is believed to mean 'laughing waters' for the spring's sound.

The 1931 Bagnell Dam on the Osage River — when built, one of the world's largest hydroelectric dams, creating Lake of the Ozarks (1,375 miles of shoreline, more coastline than California). The dam transformed the Missouri Ozarks from a remote agricultural region into a major recreation economy. The dam face is viewable from the visitors overlook; the Lake of the Ozarks State Park shoreline below is accessible for swimming and paddling.

The Lake of the Ozarks' premier full-service resort — four restaurants, a marina, and private beach access on the main channel of the lake. Tomorrow's drive north to Onondaga Cave and then to St. Louis passes through the Ozark plateau; plan for a 3-hour drive home.

A National Natural Landmark cave with among the most distinctive formations in Missouri — the 'Lily Pad Pond' is a shallow underground pool where calcite formations have grown across the water surface like flat lily pads, unique in morphology. The Cathedral Room has a 60-foot-high ceiling with massive stalactites; the Bottomless Pit is a deep sump visible from the walkway. More geologically refined than Meramec Caverns — the formations are more delicate and the cave environment less commercialized. 1.5-mile guided tour.

A German-founded river town on the Missouri River — established in the 1830s and still home to the Missouri Meerschaum Company, the world's oldest corncob pipe manufacturer (founded 1869, still producing pipes by hand). The Front Street historic district along the Missouri River has a linear park with river views, original 19th-century commercial buildings, and a strong lunch restaurant scene. Washington is less known than Hermann but equally historic; the Missouri River overlook at the end of Front Street gives a good view of the river bend.

The world's oldest and largest corncob pipe manufacturer — the Missouri Meerschaum Company has operated continuously since 1869, producing the pipes made famous by General Douglas MacArthur and Mark Twain. Visitors can watch the carving and finishing process; the factory store sells the full range of corncob pipes including the 'MacArthur' model. The Washington Historic Preservation Commission has identified 65 historic properties in the downtown grid; the old Opera House on Main Street (1889) and the Stone Church (1851) are the most architecturally significant.