Washington, Missouri | 50 minutes from St. Louis
Known as the “Corncob Pipe Capital of the World,” nearby Washington was founded in the early 1800s by German settlers. Today, many its historic downtown brick buildings and storefronts remain, and visitors can learn more about the town’s history at the Washington Historical Society Museum. There are also more than 40 wineries within an hour’s drive, or you can sample wines in town at Oak & Front Wine Bar or Olivino Tasting Bar. Washington hosts many festivals throughout the year, including Fall Festival, during the last weekend of September. The town’s farmers’ market also hosts live music and runs through October.
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Lincoln, Illinois | 2 hours from St. Louis
Named after President Abraham Lincoln, this small town is known for its historical significance and charming downtown. Lincoln never lived in the town, though it played an important role in his political rise. Discover more about this connection at the Logan County Courthouse and the Lincoln Heritage Museum. Lincoln (the town) is located along Route 66 and has the world’s largest covered wagon, with Honest Abe appropriately riding on it.
Lexington, Missouri | 3.25 hours from St. Louis
Lexington is a small town that’s rich in history. In 1864, the town was the site of the Battle of Lexington. Today, visitors can tour Lexington State Historic Site to learn about this significant battle between Union and Confederate soldiers. Lexington has four National Historic Districts with antebellum and Victorian homes that visitors can tour. From Riverfront Park, you can also see the Missouri River or take a kayak on the water. There are also several wineries and orchards just outside Lexington.
Madison, Indiana | 4.5 hours from St. Louis
Madison dates back to 1809 and has one of the best-preserved historic districts in Indiana. Lanier Mansion is a celebrated example of Greek Revival architecture in the United States, and guests can learn more about the house’s namesake, who lived there in the mid-1800s. The preserved building became a National Historic Landmark in 1994. The History and Art Center provides a look at the county’s history, including its role in the Civil War. Located in the original train station, the museum features a renovated caboose. And after seeing Madison’s historical sites, explore Clifty Falls State Park, with four waterfalls, a canyon, and hiking trails.
Galena, Illinois | 5 hours from St. Louis
Galena is best known for its historic downtown, with 85 percent of the old buildings still preserved. Most notably is Ulysses S. Grant’s former home, where you can get a glimpse of the former president’s life. With architecture dating back to the early 1800s, the town is filled with restaurants, art galleries, and antique stores. Local artisans offer classes on jewelry-making, pottery, and wood-carving. The Galena River and rolling hills add to the town’s beauty and provide plenty of options for outdoor activities, including golf, hiking, farm tours via ATV, and skiing. There are also numerous wineries in the surrounding area, including Fergedaboudit Vineyard, where patrons are invited to sit back and relax, as the name suggests.
Grafton, Illinois | 1 hour from St. Louis
Located along the Great River Road, near the confluence of the Mississippi and Illinois rivers, Grafton makes for a great day trip from St. Louis. With its limestone bluffs and proximity to Pere Marquette State Park, Illinois’ largest state park, the small town offers scenic drives, river views, plenty of opportunity for outdoor recreation. Visitors can take the Grafton SkyTour up the bluff to Aerie’s Resort for panoramic views of the river valley or stop by Grafton Oyster Bar, a floating restaurant at Grafton Harbor, for oysters and Cajun-Creole fare. The Loading Dock, a riverfront bar and grill, and Grafton Winery, which offers wine tastings and dining at its downtown location and vineyard estate, are also worth a stop.
Ste. Geneviève, Missouri | 1 hour from St. Louis
Founded around 1750, as the first permanent European settlement in MIssouri, Ste. Geneviève remains one of the best places in the country to explore French colonial history. Much of the town’s historic district has been preserved, including rare homes built using vertical-log construction. Visitors can tour Ste. Geneviève National Historical Park and the Louis Bolduc House, one of the country’s best-preserved examples of French Creole architecture, and visit the Felix Vallé House State Historic Site. Beyond its history, browse antiques at the St. Geneviève Antique Mall, see local art at Silver Sycamore Gallery, or sample Missouri wines at Weingarten Vineyard and Charleville Brewery & Winery.
Hannibal, Missouri | 2 hours from St. Louis
Hannibal is best known as the boyhood home of Mark Twain, famous for The Adventures of Tom Sawyer and other books that were inspired by his experiences growing up along the Mississippi. Visitors can tour the Mark Twain Boyhood Home and Museum and explore Mark Twain Cave, the labyrinthine cave that inspired scenes in Tom Sawyer. The historic downtown is also filled with shops, restaurants, and museums. Riverboat rides offer another way to experience the small town along the Mississippi. For a different vantage point, visitors can climb Cardiff Hill for views of the river and downtown.
New Harmony, Indiana | 2.5 hours from St. Louis
Located along the Wabash River, New Harmony was the site of two ambitious utopian communities during the 19th century, first established by the German religious Harmony Society and later by social reformer Robert Owen. Visitors can explore the town’s unusual past through Historic New Harmony and the Atheneum Visitor Center. The town is also known for its distinctive architecture and contemplative spaces, including the open-air Roofless Church and Harmonist Labyrinth, originally designed as a place for meditation and reflection. Art galleries, local shops, and nearby Harmonie State Park provide plenty of reasons to linger.
Nauvoo, Illinois | 3.5 hours from St. Louis
Along a bend in the Mississippi River, sits Nauvoo, a town shaped by Native Americans, members of the Church of Jesus Christ of Latter-day Saints, Icarians, and German immigrants. The town is best known for its role in the early history of the Church of Jesus Christ of Latter-day Saints. Visitors can tour dozens of restored homes, shops, and other sites through Historic Nauvoo. The Nauvoo Historical Society operates the Weld House and Rheinberger Museum, while the Nauvoo State Park includes the town’s first vineyard. For a break from the history, stop at Baxter’s Vineyard’s & Winery, Illinois’ oldest operating winery, or walk the Trail of Hope down to the Mississippi River.
