Drive right into history, gaze at stunning river views, see an eagle or two, and stop to sip some wine on this 55 mile driving tour. Take a moment on the tour to check out the antebellum homes. See if you can find the cannonball stuck in a column.

THIS UNIQUE DRIVE mixes history with five Missouri wineries. You’ll follow the historic Santa Fe Trail on several sections of this route along Highway 24 and the older Route 224 spur in Lafayette County. Central to the route is the town of Lexington, site of four historic districts.

Highland Drive offers magnificent views of the Missouri River Valley from atop the WWI Memorial right off Highland at Wall Street. You’ll see stunning antebellum homes along this road, along with the iconic Madonna of the Trail monument at Highland and Main (Route 224).

Photos Courtesy of Lexington Tourism

Downtown Lexington showcases the Lafayette County Courthouse, the oldest west of the Mississippi. Immediately to the west of the courthouse is the Lafayette County Veterans Memorial. All within a few blocks, this quaint district offers shopping, restaurants, two museums, historic monuments, and an interpretive walking and driving trail. 

Go north on 10th Street to Riverfront Park. Thriving river commerce helped establish Lexington in the 1800s. From this point, you might be lucky enough to spot bald eagles that nest along the riverbanks.

East on Main and north at the stoplight, you’ll find the Battle of Lexington State Historic Site with a visitors center and a historic battle site with an interpretive trail. At the site, you can tour the Anderson House, a battle-scarred home caught in the crossfire during the Battle of Lexington. Take a jog off Route 224 to visit the Forest Grove Cemetery containing several generations of African American slaves and their descendants. Continuing east you can hook up with Highway 24 and head on to two different wineries on the way to Waverly where you will be able to head south on Route 23 to I-70.

If you head east on Route 224 or Highway 24, you can access three more wineries on this tour and then be on your way toward Kansas City to access I-70, I-35, or I-29.


1. Highland District, Lexington
2. Missouri River Valley Lookout, Lafayette County WWI Monument, Lexington
3. Madonna of the Trail, Lexington
4. Downtown District, Lexington
5. Riverfront Park, Lexington
6. Lafayette County Veterans Memorial, Lexington
7. Battle of Lexington SHS, Lexington
8. Anderson House, Lexington
9. Forest Grove Cemetery, Lexington
10. Terre Beau Winery, Dover
11. Baltimore Bend Vineyard, Waverly
12. Fahrmeier’s Family Vineyards, Lexington
13. La Bella Vineyards & Winery, Wellington
14. Odessa Country Winery, Odessa
15. Arcadian Moon Winery, Higginsville

Learn more about Lexington’s Civil War history here.

Article originally published in Missouri Life’s Scenic Rides and Drive Guide 2023.