Right on the banks of the Missouri River, in the heart of wine country, sits Hermann. With its roots tracing back to German settlers, today, the town still boasts an old-world charm with historic, German-style homes lining the streets. To soak in the beauty of the town, stop by Hermann Farm, where you can tour the grounds and learn about the early days of wine-making in the area. You will also get a firsthand look at what farm life was like in Hermann in the 1840s by visiting the onsite Teubner-Husmann Greek Revival home. After learning about Hermann’s wine-making history, enjoy a glass for yourself while visiting Stone Hill Winery. There, you can take a guided tour of the largest series of arched underground cellars in the country and browse the winery’s museum room before sitting back and relaxing with a tasting. Hermann is proud of its German history, and the best place to learn about the immigrants that made the town what it is is to visit the Deutschheim State Historic Site. As you tour the historic houses, you will learn more about Hermann’s early settlers and see where the first German newspaper was published west of the Mississippi.

Just across from the Kansas border, you will find the charming small town of Weston. Affectionately known as the best small town in Missouri, taking a trip to Weston feels like stepping back in time, particularly as you stroll through its historic downtown. There is no better place to see what makes the town special than Weston Bend State Park, where trails offer unmatched views of the Missouri River. Whether hiking or biking through the park, it is equally beautiful on sunny summer days and crisp autumn afternoons, where there is no shortage of eye-catching foliage. During the winter, head over to Snow Creek, Weston’s top spot for skiing, snowboarding, and snow tubing. With activities fit for beginners and advanced adventurers, there is something for the whole family to enjoy at the resort. Another popular Weston spot is the Holladay Distillery, which dates back to 1856. While the company now uses modern distilling techniques, its Mississippi bourbon recipe is 160 years old. You can taste it for yourself after touring the stillhouse.

Situated near the Mississippi River, between St. Louis and Cape Girardeau, you will immediately notice Ste. Geneviève’s French colonial roots. Settled by French Canadians in the 1730s, Ste. Geneviève is the state’s oldest permanent European settlement, which you can see in its eighteenth-century architecture that still lines the streets. You can learn more about the town’s history by visiting The Bolduc and LeMeilleur Houses at the Centre for French Colonial Life Museum. There, you can experience the town’s history in a hands-on way, taking a guided tour of the houses that were built in 1794 and 1820, respectively. What makes Ste. Geneviève stand out as a stunning Missouri town? It has numerous beautiful outdoor areas. Head to Hawn State Park to walk through towering pine and oak trees, see impressive exposed rocks and watch native birds fly overhead. The nearly 5,000-acre park also has campsites, so you can spend a weekend out in nature. Another popular outdoor spot is Pickle Springs Natural Area. The eye-catching waterfalls and cool canyons are home to Missouri wildlife like the four-toed salamander and over 250 different plant species.

Augusta is less than 50 miles west of St. Louis and another popular spot in Missouri’s wine country. One of the easiest ways to explore the different vineyards around Augusta is to hop on one of the wine trolleys, which run on Saturdays from May to October. Running in a continuous loop, the hop-on/hop-off trolleys allow you to explore downtown Augusta and popular area vineyards like Montelle Winery, which overlooks the Missouri River Basin. If you prefer apples to grapes, make your way to Centennial Farms and Orchard, an Augusta family farm that has been in operation since 1854. The farm’s timber-framed barn is on the National Register of Historic Places and contains a market where you can shop for seasonal goods like blackberries, apple butter, and raw honey. If you would like to explore the Missouri River Valley, take a trip to Augusta’s Klondike Park, which is known for its picturesque views. With a mix of natural and paved trails and a fully stocked fishing lake, it is easy to spend a whole day exploring the park.

Just over 10 miles outside of Kansas City, Missouri, Parkville is a charming, historic town that perfectly embodies “small-town America.” As you stroll down Main Street, you will find local restaurants, boutiques, and festivals throughout the year that will make you feel right at home. Outside of its historic downtown, you will find the breathtaking Parkville Nature Sanctuary, which spans 115 acres and has nearly three miles of hiking trails to explore. While you are there, keep a lookout! You just might spot local wildlife roaming around, like deer, frogs, turtles, and colorful butterflies. Another popular outdoor spot in Parkville is English Landing Park. There is plenty to do in the park, with a sand volleyball court and disc golf course onsite, a large playground for the kids to enjoy, and a boat ramp for easy access to the water. If you cannot get enough of the great outdoors, you will love visiting the Heartland Retreat Center, which hosts a variety of activities like a high ropes course, archery, horseback riding, and more for family members of all ages.

Another picturesque town on the Missouri River, Boonville offers the perfect blend of charm, history, and beauty. Katy Trail State Park, which is the longest developed rail trail in the country, goes right through Boonville, making it a popular spot for local nature lovers. You can hit the trails on foot, on a bicycle, or even on a horse as you enjoy views of the Missouri River and geologic sites. From the trails to the road, Boonville has it all! Gear heads will love exploring Lewis Miller’s Mitchell Collection, which is the most extensive collection of vehicles from the Mitchell Motor Car Company. Visits are by appointment only, so plan ahead to view this extensive collection that includes wagons, cars, motorcycles, and bicycles from the nineteenth and twentieth centuries. Boonville’s most famous residents are not people but horses. Head to Warm Springs Ranch, which is the official breeding facility of the iconic Budweiser Clydesdale horses. As you tour the ranch, you will learn more about how the Clydesdales are raised and what it takes to be a hitchhorse.

Tucked in southwest Missouri, you will find Carthage. Also known as America’s Maple Leaf City, it is home to the annual Maple Leaf Festival, which celebrates the town’s beautiful foliage. Sitting on the historic Route 66, Carthage has over 550 buildings listed on the National Registry of Historic Places and plenty of beautiful spots to explore. One of the most unique places in the town is Red Oak II, which was created by an artist named Lowell Davis. Originally from Red Oak, a small town 20 miles north of Carthage, which became a ghost town, Davis bought the old buildings from his hometown to give them new life. He moved them to Carthage, where today, a general store, an old school house, a cemetery, and more sit in a perfectly preserved piece of yesteryear. While the buildings are privately owned, visitors can explore the area as long as they stay on the gravel road. History buffs visiting Carthage will want to stop by the Battle of Carthage State Historic Site. Once the spot of the earliest full-scale battle in the Civil War, today it features a spring and a quiet meadow, with historical markers where you can learn more about the history that took place on the land. Step back in time with a stop by the 66 Drive-In, one of the only remaining drive-in theaters in the country. Sitting right on Route 66, the theater showcases double features on weekends from April to October.

Right on the Mississippi River, Hannibal is best known for being Mark Twain’s hometown. Whether you are a long-time fan of the author or just want to visit a beautiful Missouri town, Hannibal will not disappoint. One of the area’s most impressive sites is the Mark Twain Cave Complex. Cameron Cave, in particular, is a breathtaking natural wonder that you can explore on either a guided walking tour or an adventure tour complete with climbing and crawling. Another popular spot for visitors is the Mark Twain Memorial Lighthouse, on top of Cardiff Hill, which was featured in some of Twain’s works. While there, you will enjoy impressive views of the Mississippi River, perfect for professional or hobby photographers. To see more of Hannibal’s beauty, head to Lover’s Leap, which is a five-acre park that sits on a bluff in town. From the park, you can see across the Mississippi River into Illinois and use the public shelters and grills to set up a picnic with a view.