The Great River Road, the Katy Trail and Route 66 in 6 Days

Start on Hill Street in Hannibal at the Mark Twain Boyhood Home, the house Samuel Clemens grew up in between 1844 and 1853. Its nine buildings line Hill and Main, with the Rockwell paintings in the gallery on Main; check its site for hours and give it two hours or more. A few blocks north, Jim's Journey tells the life of Daniel Quarles, held in slavery on the Quarles farm, whom Clemens credited as the original of Jim, and of Black Hannibal after him. It opens by appointment, so call ahead. Then take Route 79, the Great River Road, south past Louisiana, Clarksville and Elsberry, about an hour and a half with the Mississippi close by, and cross into St. Louis County on I-70 and I-270. Leave the interstate at Riverview Drive for the Old Chain of Rocks Bridge, a mile of 1929 truss with a bend halfway over, now open only to walkers and cyclists; the walk to the bend and back takes an hour. Head south toward downtown on Riverview Drive and Hall Street. Beside the riverside trail, north of the Merchants Bridge, is the Mary Meachum Freedom Crossing, where on May 21, 1855, Mary Meachum set out by boat with nine freedom seekers. Stay downtown for the night.

Be at the Gateway Arch when the visitor center opens at 9. The museum under its legs is free, and the tram to the top, a ride that takes most of an hour with the wait, runs on timed tickets, so buy them ahead. The Arch stands where the French town was, on forty blocks cleared after a 1935 bond vote that turned out to be rigged. Walk west across the grounds to the Old Courthouse, which reopened in May 2025 with new galleries on Black St. Louis and the Scotts. Enslaved people were sold at its east door until 1861, and in its courtrooms Dred and Harriet Scott brought their freedom suit, one of more than three hundred freedom suits heard there; ranger tours run most days at 2:15. Leave downtown by mid-afternoon for the two-mile drive west to Delmar Boulevard and the Scott Joplin House, the flat where Joplin wrote The Entertainer. In 1983 it became Missouri's first state historic site for African American heritage, and its tours start on the hour. Then take I-70 west, about half an hour, to St. Charles, and walk the brick Main Street in the evening.

Give the morning to the St. Charles riverfront. The First Missouri State Capitol is the pair of brick buildings on Main Street where the legislature met from 1821 until the Jefferson City capitol was ready in 1826; its interpretive center is free, and guided tours cost a nominal fee. Down on the river, a boat house and museum keeps working replicas of the boats the Corps of Discovery took up the Missouri from here on May 21, 1804. Leave by 11:30 on Route 94, the road up the Missouri, west by way of Defiance, Augusta and Marthasville, with the Katy Trail beside it much of the way. Route 19 crosses the river to Hermann, a little over two hours from St. Charles, for the 2:30 tour of Deutschheim, two houses of the 1840s that the state keeps as the home the German settlers made here, with a printing press in one and a brick winery beside it. Cross back on Route 19 and follow Route 94 west along the north bank, about an hour and a half, to the US-54 bridge into Jefferson City.

Take the 11 o'clock tour of the Missouri State Capitol, reserved at least a day ahead. The 1917 building holds the State Museum on its first floor and, in the House Lounge, the Benton mural of the state's social history, which takes in slavery, Jesse James and Tom Pendergast. About a mile south, walk the hill campus of Lincoln University, founded in 1866 with $6,400 raised from the army pay of the Black enlisted men of two Missouri regiments, the 62nd and the 65th U.S. Colored Infantry; their memorial plaza is on the quadrangle. Then take US-63 north and I-70 west, about an hour, to Rocheport, where the first section of the Katy Trail opened in 1990. An hour on foot takes you through the railroad's stone tunnel and back. Route 240 runs on to New Franklin, and Routes 5, 87 and 187 lead to Boone's Lick, the salt spring Nathan and Daniel Morgan Boone began working in 1805, where a short trail goes down to the springs. Its name spread to the road west from St. Charles and to the whole country around it. Route 87 runs back south and over the river to Boonville for the night.

Drive Route 41 to Arrow Rock, about half an hour, and be at the visitor center when it opens at 10. The whole village is a National Historic Landmark: a busy landing of more than 1,000 people once, about fifty today. Enslaved people raised the hemp and tobacco the Boonslick lived on and built much of the town, and in 1880 more than half the town was Black. Walk past Joseph Huston's tavern of 1834, which still serves meals, to the painter George Caleb Bingham's house and the stone calaboose. Leave by 11:30. The drive to Springfield, by I-70 east and US-65 south through Sedalia, is about three and a half hours. On Sundays the History Museum on the Square is open from 1 to 5, on Park Central Square, where old Route 66 comes in on St. Louis Street. One gallery tells how the highway was given its number from Springfield's Colonial Hotel in 1926. Another covers the Osage, Kickapoo and Lenape who lived here, their removal west, and the Trail of Tears through the town.

Start at Wilson's Creek National Battlefield, twenty minutes southwest of Springfield. On August 10, 1861, Union and Southern armies fought here in the first big Civil War battle beyond the Mississippi, and Nathaniel Lyon was killed on Bloody Hill, the first Union general to die in the war. See the museum in the visitor center, then drive the five-mile tour road past Bloody Hill and the 1852 Ray House. Take I-44 west to Halltown, where Routes 266 and 96 carry old Route 66 by Paris Springs and Avilla into Carthage. The Boots Court, a motor court of 1939 at the corner where 66 met the Jefferson Highway, rents all 13 rooms again, still without televisions; come back at dusk for the neon. South of Carthage, I-49 and Route 59 lead to Diamond and George Washington Carver National Monument, free and open daily from 9 to 5, on the farm where Carver was born into slavery as the war ended. Congress made it in 1943, the first national monument honoring an African American. Give the visitor center's film its 28 minutes and walk the trail through woods and prairie to the 1881 Moses Carver house. Joplin is about half an hour west, where Madison and 7th streets carry old 66 on to the Kansas line.