Cape Girardeau, MissouriSteven Liveoak/Shutterstock
Halfway between St. Louis and Memphis, Cape Girardeau gives tired visitors a great place to stay the night—or two. A winner of the Great American Main Street Award, the river town blends historic charm with modern technology, and some of the shops on the main street have been in business for more than 75 years. The city has 57 registered structures on the National Register of Historic Places, along with a creative corridor that boasts public art and a children’s museum. This is how every state in America got its name.
Covington, KentuckyFernando Garcia Esteban/Shutterstock
Located just across the Ohio River from Cincinnati, Covington offers a revitalized Main Street to visitors and locals. Anchored by the Carroll Chimes Bell Tower, Main Street offers a mix of Midwestern and Southern charm in an area that is seeing an influx of independent businesses. Brimming with beautiful Italianate brick buildings and public art, Covington’s Main Street is a great day trip.
Howell, MichiganRungtiwa P/Shutterstock
For a historic weekend, look no further than Howell, Michigan. Many of the buildings have not been changed since the city was incorporated in 1863, and the Italianate buildings dot the street. Two high Victorian façades, a Victorian Gothic church, a modified English Gothic Church, a Tudor Revival office building, and the original Opera House are some architectural standouts. The main street has more than 40 specialty retailers and restaurants, and it is also the location for many events and festivals throughout the year. With initiatives to encourage residents to buy local, this main street offers both charm and neighborly values.