1 hour
The 13-acre historic district downtown is one of the newest entrants to the National Park Service system, and enhanced signage and interpretive programming illuminate the area’s French colonial roots and its intact architectural heritage. That introduction is a great gateway to the larger region, which boasts many excellent wineries, including Chaumette Vineyards & Winery (a destination staycation with exquisite villas and a top-notch restaurant) and Crown Valley (also home to a brewery, a distillery...and a tiger sanctuary).
1 hour, 45 minutes
Perhaps most notable for America's National Churchill Museum, Fulton was the site of the British prime minister’s famous “Iron Curtain” speech. In honor of his efforts towards peace, a large section of the Berlin Wall forms a sculpture near the museum, on the campus of Westminster College. For transportation and history buffs, the Auto World Museum showcases everything from a doctor’s horse-drawn buggy from the 1880s to that ‘80s marvel, the DeLorean Coupe; they even have the Mizzou Sun Tiger II, a solar-powered vehicle developed by students for a 1997 race. Downtown, the Brick District features blocks of independent stores, restaurants, historical sites, and a theater.
Arrow Rock Lodge No. 55
2 hours, 30 minutes
Listed in its entirety as a National Historic Landmark, the village's famous residents have included the artist George Caleb Bingham and Dr. John Sappington, who developed and mass-marketed quinine as an anti-fever and anti-malarial remedy. Though relatively small, the town offers plenty to do: Catch a live show at the Lyceum Theater, enjoy a meal at J. Huston Tavern (which claims to be the oldest continuously operating restaurant west of the Mississippi) or Catalpa (which recently transitioned from fine dining to burger joint), and stay at one of the cozy lodging options in the area.
3 hours, 45 minutes
If you’re biking the Katy Trail, the westernmost trailhead is here, 225 miles from St. Charles. Stop at the restored Katy Trail Depot, situated on the largest town square in Missouri, which offers a plethora of retail and dining/drinking establishments. A complex of historic buildings also makes up the Henry County Museum and Cultural Arts Center, a village set up with exhibits, costumed docents, and period representations of homes, offices, shops, and a school.

Via Flickr/ Pom Angers
4 hours
Rebuilt during the Victorian era (after being burned to the ground during Civil War skirmishes), Carthage now comprises more than 600 buildings on the National Register of Historic Places, including one of the largest such residential districts in the state. In the center of town, the impressive Romanesque Revival Jasper County Courthouse makes an excellent photo op, and all along Route 66, sites like the Civil War Museum and the Precious Moments Chapel & Gardens (it’s more than just wide-eyed figurines) will keep you busy. One don’t-miss is Red Oak II, an artist-recreated “ghost town” made up of vintage buildings (think gas station, general store, church, and cafe) carefully relocated and restored here from their original site, the village of Red Oak, that once thrived about 18 miles away. Stroll the town and get a glimpse of a bygone slice of rural American life.