Top Hidden Gems to Explore on Interstate 55: A Ultimate Road Trip Guide

What to know before you hit the road.

Cross-country road trips typically bring to mind coast-to-coast travels, beginning your journey in California or Washington and ending somewhere in New Hampshire, or even Maine. However, there’s more than just one way to traverse the country. If you’re not going east to west, you can just as easily go north to south and have an equally enjoyable experience, while touching upon major cities like Chicago, St. Louis, and Memphis, ultimately arriving in Chicago via Interstate 55.

Where to Find Interstate 55

Commonly mistaken for Highway 55, Interstate 55 is a major cross-country highway that spans 964 miles from LaPlace, Louisiana to Chicago, Illinois. Moreover, while the aforementioned cities are all necessary pit stops along this road, there are some incredible lesser-known attractions that one could explore along this route.

One Day in Chicago

Where to Stop

Beginning your trip at LaPlace, you’ll drive north through Louisiana for about 66 miles, with approximately 20 miles spent crossing the Manchac Swamp Bridge, one of the longest water bridges globally. If you’re willing to take a detour, the vibrant city of New Orleans is just 30 miles east via I-10 E.

If you prefer to stay in your car, consider cruising down Esplanade Avenue, which spans from the stunning French Quarter to City Park and showcases charming townhouses and oak-lined streets. If you’re willing to park and stretch your legs, hopping on a historic streetcar or strolling down the iconic Bourbon Street is your best bet for a quick-yet-fulfilling pitstop.

Once you’ve finished your detour and are back on Interstate 55, you’ll be set to enter Mississippi. About 100 miles into your journey through the Magnolia State, you’ll arrive in Jackson, Mississippi’s capital. Make a stop at the Old Capitol Museum, Jackson’s oldest building, constructed in 1839, which served as the state’s government seat until 1903. This distinguished building, topped with a copper dome, exemplifies Greek Revival architecture—making it perfect for a photogenic moment for history buffs on your trip.

If you’re in the mood for a stroll around the city, consider exploring Fondren District, a bustling hub filled with small businesses, art boutiques, and cafes. For an educational experience about Jackson’s history, visit the Agriculture Museum, which delves into Mississippi’s agricultural lifestyles, both past and present.

After leaving Mississippi and entering Tennessee, you’ll find yourself in the heart of blues and rock ‘n’ roll—the city of Memphis. Memphis is renowned for the legends who got their musical start there, such as Elvis Presley and Johnny Cash, who both recorded albums at the famed Sun Studio, making it essential to tour Graceland Mansion, which provides an intimate look at Elvis Presley’s home.

Continue the musical journey with a trip down Beale Street, where you can visit the Memphis Music Hall Of Fame, B.B. King’s Blues Club, or stroll down Main Street to the Orpheum Theater, a revitalized venue originally known as the Grand Opera House. Now famous for offering Broadway shows, comedy acts, and other special events, the Orpheum has a rich history.

After stopping in Memphis, you’ll drive nearly 300 miles to reach St. Louis, Missouri, one of the largest cities in the Great Plains, brimming with history and culture. You’ll undoubtedly want to visit the iconic Gateway Arch. While you may have seen countless photos of the structure established by the National Park Service in 1935, experiencing a tram ride to the top—over 600 feet in the air—offers breathtaking views from the tallest man-made monument in the U.S.

A notable attraction worth exploring is Forest Park, a sprawling 1,371-acre area that hosted the 1904 World’s Fair. While it may not be Central Park, you might be surprised to realize it’s a colossal 528 acres larger than the famed New York City landmark.

After traversing through many states, you’ll finally reach the final—yet certainly not least interesting—state of Illinois. A trip to the Prairie State isn’t complete without visiting Springfield. Known as the “Land of Lincoln,” you can pay your respects at the Lincoln Tomb. This 117-foot-high granite obelisk offers a distinctive tribute to President Lincoln, his wife Mary Todd Lincoln, and three of their four sons buried there. The memorial’s interior includes excerpts from Lincoln’s Gettysburg Address and the Second Inaugural Address, along with 16 pilasters honoring Lincoln and the 15 presidents who came before him. This historical site provides an educational and informative experience for history enthusiasts.

You’ll likely spend time in Chicago as well, since Interstate 55 follows the Stevenson Expressway to U.S. 41 (the lovely Lake Shore Drive), situated right off Lake Michigan. Roll down your car windows—or park and walk the Lakefront Trail, which embraces the gorgeous shoreline. If you’re traveling with adventurers, head to Navy Pier for a ride on the famous Ferris wheel offering unbeatable views of the city from the top.

If you’d like to experience somenatural beauty before entering a bustling metropolis, consider stopping in Lisle and spending time at the Morton Arboretum. Covering nearly 2,000 acres of rolling hills and lush foliage, it offers whimsical and breathtaking scenery. Joy Morton, founder of the Morton Salt Company, envisioned this botanical garden alongside the Sterling Morton Library, which houses nearly 30,000 volumes focused primarily on botany and horticulture.

This journey brings your voyage up north—along this highway, bustling cities meld with rural communities, and nature’s serene rivers meander toward iconic architecture for almost 1,000 miles. Consequently, take the time to appreciate and enjoy the unique destinations scattered along this not-quite-cross-country trip.

Good to Know

Along this 964-mile-long journey, which loosely traces the Mississippi River, expect a fluctuating road that alternates between a busy thoroughfare and a peaceful, rural freeway. Traffic is likely to swell and dissipate throughout your drive.