What lies at the end of the path? A trail in Route 66 State Park
What lies at the end of the path? A trail in Route 66 State Park

Your Three-Point Itinerary

You may have heard that there are kicks to be had driving the fabled road known as Route 66. We recommend the stretch from Madison, Illinois to Eureka, Missouri, but you’ll have more fun if you get out of your car and take in the local color as you wind your way roughly 40 minutes south of St. Louis. (If you base your excursion in St. Louis, you can fill your evenings with live blues, jazz, and regional cuisine.) Here, three sights worth stopping for along the highway known as America’s Main Street, which traverses the Mississippi River in northeastern Missouri:

  1. Stop #1: The Chain of Rocks Bridge
    This 5,353-foot-long pedestrians/cyclists-only pathway between Madison, Illinois and St. Louis offers panoramic views of the Mississippi River and the Gateway Arch. The 83-year-old span—too narrow for today’s cars—connects to the St. Louis Riverfront Trail on the Missouri side. To get there from the Illinois side, take I-270 west and exit at State Route 3 south. Go west on Old Chain of Rocks Road and look for parking just before the bridge. For more info, click here.
  2. Stop #2: Route 66 State Park
    Packed with Route 66 memorabilia, the park’s visitors’ center was a roadhouse in the 1930s, when the site was a planned resort community called Times Beach. Since 1999, the 420-acre parcel on the Meramec River has been a state park, with seven miles of trails for hikers, cyclists, and horseback riders. Watch out for bluebirds, wild turkeys, and the occasional bobcat. 97 N. Outer Rd. E., Suite 1, Eureka, 636-938-7198, mostateparks.com.
  3. Stop #3: Meramec Caverns
    Time was when people stayed away from the seven-story cave in Stanton, Missouri, because it was a favored hideout of Jesse James. Since the mid-1930s, it has been open to visitors who want to get a view of the majestic limestone caverns far beneath the surface. Meramec Caverns also offers treetop views, via swinging bridges and ziplines. Canoes are available for rent if you want to take in the scenery from a floating perspective. 1135 Route W., Stanton, 573-468-6072, visitmo.com.

Where to stay: The Fleur-de-Lys Mansion (3500 Russell Blvd., St. Louis, 314-773-3500, thefleurdelys.com offers four luxurious, antique-filled rooms in St. Louis’s historic Compton Heights neighborhood; rates range from $205 to $305 a night. Elves Manor (4149 W. Pine Blvd., St. Louis, 314-568-0236, elvesmanor.com has spacious quarters suitable for up to six in a carriage house in the West Pine-Laclede National Register Historic District; rates range from $160 to $345 a night.

Where to Dine: The 1860 Saloon and Hard Shell Café (1860 S. 9th St., St. Louis, 314-231-1860, soularddining.com offers live blues nightly alongside fresh oysters, shrimp, and seafood gumbo. BB’s Jazz, Blues, and Soups (700 S. Broadway, St. Louis, 314-436-5222, bbsjazzbluessoups.com also features live music; its menu includes signature St. Louis dishes such as toasted ravioli, red beans and rice with andouille sausage, and po’ boy sandwiches.


Photography: Courtesy of the Missouri Department of Natural Resources