17 Best Road Trips From St. Louis, Missouri - Updated 2024

road trips from st louis
Ryan Joshua
Ryan Joshua 
| 8 min read

All of us deserve a break from all of the stresses that we encounter in our daily lives. Despite St. Louis, Missouri has some of the best hotels with or near casinos and amazing vacation home rentals, some people would rather not have a staycation and would prefer to vacation and travel elsewhere. While the best way to travel is by air, as it is the fastest mode of travel, more and more people, especially millennials, try to take the high road and go on a road trip. In such cases, the travel itself becomes a major part of the vacation. Whether it is traveling by road or to another town or city, or traveling interstate, road trips are really fun, especially when you get to do it with the people you love. Are you visiting the bustling city of St. Louis in Missouri or are you a resident looking forward to a great vacation or a romantic getaway here? Continue reading to explore the best road trips from St. Louis, Missouri.

1. Chicago, IL

Navy Pier NW
Source: Photo by Wikimedia Commons user Sea Cow used under CC BY-SA 4.0

Chicago, often dubbed the “Windy City,” is a metropolis teeming with architectural marvels of the Loop and the iconic Cloud Gate sculpture in Millennium Park. The dynamic culinary scene offers a taste of world-famous deep-dish pizza and gourmet hot dogs.

Visit the Art Institute of Chicago to marvel at renowned artworks or take a scenic stroll along the Navy Pier, offering spectacular views of Lake Michigan. Explore the city’s rich history at the Chicago History Museum or immerse yourself in the sports culture by attending games at historic venues such as Wrigley Field or United Center. There’s also no shortage of beautiful parks, including Grant Park and Lincoln Park.

The distance from St. Louis, Missouri, to Chicago spans approximately 297.2 miles (478.30 kilometers), and the drive typically takes around 4-5 hours via I-55 N. Enjoy the glitz of Chicago before you head back to your Airbnb vacation rental.

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2. Cincinnati, OH

Downtown Cincinnati viewed from Mt. Adams (cropped)
Source: Photo by Wikimedia Commons user EEJCC used under CC BY-SA 4.0

At Cincinnati, you can start your journey in the historic Over-the-Rhine district, known for its beautifully preserved 19th-century architecture and lively arts scene. Don’t miss a ride on the iconic Cincinnati Bell Connector streetcar, which offers a convenient way to explore the city. Be sure to explore the Cincinnati Art Museum, showcasing an impressive collection of art spanning centuries, or visit the Cincinnati Zoo & Botanical Garden for a family-friendly adventure. For sports enthusiasts, catching a Cincinnati Reds baseball game at Great American Ball Park is a must.

The city also boasts a thriving culinary scene, with renowned chili parlors and craft breweries amid sweeping vistas of the skyline. A trip wouldn’t be complete without a view from the top of Carew Tower.

Cincinnati is about 350 miles (563.27 kilometers) from St. Louis, and driving via I-70 E and I-74 will take over 5 hours from your 5-star hotel.

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3. New Orleans, LA

New Orleans, Louisiana
Source: Photo by Flickr user Pedro Szekely used under CC BY-SA 2.0

Known for their very colorful and historic downtown area, the city of New Orleans in Louisiana is a must-visit for travelers of all ages. Experience the fun and enjoyable festivals, dine in their restaurants, and spend your trip traversing the whole Bourbon Street for top-shelf and even rare whiskeys. New Orleans is also home to the country’s oldest historic areas because of its rich French past. You can find a lot of museums, galleries, restaurants, bars, and performers on the streets. New Orleans, LA, is a vacation spot within 10 hours of St. Louis. Just drive via I-55 S to reach New Orleans.

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4. Columbus, OH

Source: Photo by Flickr user GPA Photo Archive used under PUBLIC DOMAIN

Named after the famous explorer Christopher Columbus, the city of Columbus is the capital of the state of Ohio and has a lot of interesting places for you to explore and visit. In fact, Columbus is known for being home to one of the biggest universities and also to one of the most popular football schools in the whole of North America. The city also values its nature and environment. Therefore, you will find the best municipal parks in the whole United States at Columbus. It is also where you can find one of the best zoos in the whole country. It should take you about 6.5 hours to reach Columbus via I-70 E.

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St. Louis Tour Guide

Melissa Smith

Melissa Smith

I began my guiding career as a teenager in St. Louis, where I was born and raised. I first volunteered as a guide for the Chatillon-Demenil Mansion in South St. Louis. There is where I fell in love with history and its effect on present day. From my teenage years as a volunteer, I progressed to a job at the Missouri Botanical Garden where I trained and supervised the School Program Volunteer Docents and Instructors. My love for the outdoors comes from this experience of guiding school groups and chaperones through the spectacular 79 acres of the world’s 3rd most renowned botanical garden. Right here in my home town! From there I’ve gone on to work for the National Park Service as a Seasonal Park Ranger. This has been a most rewarding and delightful experience! I have guided travelers at such wonders as Arches National Park in Moab, Utah, and lesser known parks like Voyageurs National Park in International Falls, Minnesota. I have served two seasons at the Gateway National Park in St. Louis and have been to the top of the Gateway Arch over 200 times! Each time was a unique experience. I witnessed 3 marriage proposals, 1 military reenlistment ceremony, and 1 choir singing their award-winning songs. Most recently I have been guiding tours of Forest Park, the Central West End, and downtown St. Louis. I hope you’ll join me on one of my walking tours. I can’t wait to share with you St. Louis, and our rich cultural history!

Tours by Melissa

5. Grand Rapids, MI

Flat Iron Building
Source: Photo by Flickr user Scottb211 used under CC BY 2.0

There are a number of great driving trips from St. Louis, but Grand Rapids, MI is definitely a must-go. Located right next to the breathtaking Grand River is the city of Grand Rapids in Michigan. You can find almost everything in the city, but they are mainly known for their rich arts and culture. There are a lot of art museums and galleries which you can visit, aside from the annual art competitions and outdoor exhibits that the city hosts. For history enthusiasts, there are also a lot of museums, monuments, and zoos that you can find around the city. You can take the I-55 N route. It takes about 7 hours via this route to Grand Rapids.

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6. Pittsburgh, PA

Source: Photo by Flickr user GPA Photo Archive used under PUBLIC DOMAIN

Pittsburgh in Pennsylvania, also known as the City of Bridges, is another historic place that may interest you. The remnants of its very rich past in the steel industry are still evident in the city’s major thoroughfares. From those red-brick buildings, numerous warehouses and arched bridges, you will surely fall in love with its very industrialized feel. Today, the city is turning into a gastronomical city that houses a lot of amazing restaurants and shops. It takes about 10 hours to reach this destination via I-70 E.

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7. Washington D.C.

White House
Source: Photo by Wikimedia Commons user [Unknown] used under PUBLIC DOMAIN

We all know that Washington D.C. is where the seat of the government of the United States is. But aside from the usual historic monuments and places such as the official residence of the president of the United States of America, the White House, and other government buildings, you can also try doing some other touristy stuff like shopping and eating at Georgetown. While you check out the United States Capitol, Library of Congress, Lincoln Memorial, Washington Monument, National Mall, and Smithsonian Institution Offices,you can also engage in a photo shoot at National Arboretum. It takes almost 13 hours to reach this destination via I-70 E.

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8. New York

New York City
Source: Photo by Flickr user Yoann JEZEQUEL used under CC BY 2.0

The Big Apple is surely everyone’s dream destination. Being one of the world’s major cities, New York City has a lot to offer. Take a selfie in front of the Statue of Liberty, get to know what happened during the 9/11 attacks at the World Trade Center Memorial, climb to the top of the Empire State Building, ride a ferry to Staten Island, or join the crowd at Times Square. You can also cross the Brooklyn Bridge, stroll around Central Park, and accomplish so much more. New York is home to the world’s most affluent shops, boutiques, and restaurants, although there are also a lot of choices for the budget traveler. However, New York isn’t going to be a quick road trip from St. Louis. If you take the I-70 E, you can expect to drive for about 15 to 16 hours depending on the traffic.

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9. Chattanooga, TN

Source: Photo by Flickr user London looks used under CC BY 2.0

Chattanooga in Tennessee offers a one-of-a-kind adventure and experience, especially to people who live on adrenaline rush. The city also has a very laid-back feel that makes it a very relaxing place for you to visit. There are a lot of small yet very informative museums, shopping opportunities at local and international shops, and dining at some of the best restaurants in town. Wake up to the beauty of the Appalachian Mountains and walk along the side of the Tennessee River.

If you’re looking for places to visit that are within 8 hours of St. Louis, Chattanooga is an idyllic choice. Taking the I-24 E can help you reach it in 7 hours or less.

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10. Orlando, FL

Universal Orlando
Source: Photo by Flickr user LunchboxLarry used under CC BY 2.0

Orlando in Florida is indeed a destination for the kids and adults alike. It is home to some of the world’s most popular theme parks which include Universal Studios Orlando, Legoland, Seaworld, Epcot, and of course, the Walt Disney World Resort. But aside from the numerous theme parks in the city, Orlando also boasts of its great parks, beaches, dining destinations, museums, clubs and a whole lot more that your group will surely enjoy. Drive through I-24 E and I-75 S to Orlando. It usually takes 15 hours excluding the pit stops.

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11. Virginia Beach, VA

Virginia Beach
Source: Photo by user Nicolas Henderson used under CC BY 2.0

There is just one thing that comes into our minds when we speak about Virginia Beach; miles of amazing sand of the Atlantic beaches, serene oceanfront, and a myriad of outdoor activities that the city offers. This makes Virginia Beach one of the best destinations. Aside from the beaches, there are also a number of nice parks and other tourist spots that everyone can enjoy. Take the I-64 E, which is about a 15-hour drive to Virginia Beach.

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12. Baltimore, MD

Harlem Park, Baltimore, MD
Source: Photo by Flickr user Baltimore Heritage used under CC0

Baltimore in Maryland, known as the Charm City, is known for its amazing Inner Harbor that has been duplicated all around the world. It is also known for its rich history, mainly the historic buildings in the city. Today, Maryland has become a very modern city with the rise of new specialty hotels, delectable restaurants, and festive events that made it the \“coolest city on the East Coast.\” Baltimore indeed offers a very modern experience without losing its rich history. Its a 13-hour drive via I-70 E.

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13. Milwaukee, WI

Milwaukee, Wisconsin
Source: Photo by Flickr user Josué Goge used under CC BY 2.0

Get behind the steering wheel and head on to Cream City, also known as Beer Capital, Milwaukee, Wisconsin. Located 373.6 mi (601 km) north of Saint Louis, it will take about 5 hours of nonstop driving for you to reach your destination. However, you might want to consider a two-day drive because there is plenty to see and experience between the two cities.

There is Delavan Lake, Ellwood House Museum, and the Starved Rock State Park where you can spend the night. On the next day, detour to Springfield, Illinois, and visit Abraham Lincoln Presidential Museum and Library. Have a glimpse of Cadillac Ranch in Old 66 before arriving at your destination, where you can have a hearty dinner at Swingin’ Door Exchange or at Sanford. All these attractions make Milwaukee among the better options for weekend trips from St. Louis.

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14. Highway 36

House of Mark Twain
Source: Photo by Wikimedia Commons user Makemake used under CC BY-SA 3.0

Highway 36 is an east to west US highway with four lanes. It stretches from Saint Louis for about 2,042.4 mi (3286.92 km). It is nicknamed “The Way of American Genius” because it passes through the hometowns and museums of Mark Twain, Walt Disney, General John J. Pershing, and J.C. Penney and leads to Pony Express Museum in St. Joseph. Its road is in good shape and there is less traffic. There are gas stations in adequate intervals along the way. If you need a place to eat, Third Street Bakery offers delicious croissants. There is also a Mexican restaurant in St. Francis called Park Place. The Missouri Department of Transportation and Missouri Highway 36 Heritage Alliance produced a CD that you can play in your car. It gives a narrative of all the places you visit along the way. Get yourself one before you start this journey.

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15. New Harmony, IN

Downtown New Harmony Indiana
Source: Photo by Wikimedia Commons user Timothy K Hamilto... used under CC BY 3.0

If you drive the 144-mile (232-km) stretch of the road east of Saint Louis, you will reach New Harmony, a historic town often described as being established ahead of its time. Founded in 1814 by a group of 800 Pietists from Württemburg, Germany, New Harmony is said to be a spiritual sanctuary before turning into a haven for international scientists, scholars, and educators who sought equality in communal living. While you can finish the drive in a little over two hours, you wouldn’t want to miss the interesting places along the way, which include Nashville, Mount Vernon, and Grayville. When you reach your destination, don’t forget to visit the historic New Harmony Atheneum, Harmonie State Park, and Roofless Church, to name a few.

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16. Springfield, MO

FoundersPark 082.jpg
Source: Photo by Flickr user 20after4 used under CC BY 2.0

Springfield is a city in Southwestern Missouri known as the Birthplace of Route 66. Also, it is known as the “Queen City of the Ozarks” in reference to its location within the Ozark Plateau. Some of the attractions that make Springfield a great place to go in Missouri for weekend getaways are Wonders of Wildlife National Museum, Fantastic Caverns, and Ozark Park Trail.

If you drive 216 mi (347 km) northeast of Saint Louis, you’ll reach Springfield in 3.5 hours.

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17. Hannibal, MO

Hannibal, MO
Source: Photo by Flickr user Carl Wycoff used under CC BY 2.0

Spend an afternoon on a road trip from St Louis to Hannibal and relish the sceneries that inspired Mark Twain’s Tom Sawyer and Huckleberry Finn. The 116-mile (187-km) trip will only take about 2 hours without stops. However, you may want to drive a little slower to find some interesting stops. Take Rt. 79, also called “The Great River Road” and have a short detour at Clarksville, where you can visit distilleries, vineyards, wineries, and more. Once you reach Hannibal, be sure to visit Mark Twain Cave and Mark Twain Riverboat, and try the Haunted Hannibal Tour.

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Have a road trip of your life

All kinds of trips, whether they’re day trips, weekends trips, or even just road trips, are a great way to escape from the mundane life of the city. Spend some quality time with your family and friends. Consider these drivable vacation destinations from St. Louis on your upcoming adventure with your loved ones.

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Frequently asked questions about road trips from St. Louis

  • What major cities are six hours away or less from St. Louis?

    If you’re the type who enjoys long drives, you surely wouldn’t mind taking your loved ones on a road trip to these locations less than 6 hours away from St. Louis: i) Chicago, IL (4-5 hours), ii) Cincinnati, OH (5 hours), iii) Milwaukee, WI (5 hours), and iv) Springfield, MO (3.5 hours).

  • Which cities near St. Louis are ideal destinations for family getaways?

    Those who are planning to tag the kids along for the trip can consider pinning their maps to Cincinnati, Ohio, and Milwaukee, Wisconsin. These cities are about 5 hours away from St. Louis and feature several state parks and unique museums. If driving for extra long hours isn’t an issue, both Orlando, Florida, and Virginia Beach, Virginia, are suitable destinations.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Ryan is a Computer Engineer with a heart for traveling and writing. Born in Pasay City, Philippines, and raised in Melbourne, Australia, he is now based in the Philippines' City of Smiles, Bacolod...Read more

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