The Ultimate I-65 Road Trip
Route 66 is great and all, but Interstate 65 is not to be overlooked. Stretching from Indiana to Alabama, it's studded with destinations and detours that make for an unforgettable road trip. Image: iStock
Few things are as quintessentially American as a good, old-fashioned road trip. Route 66 often steals the spotlight, but we think I-65 deserves equal billing. Stretching from Mobile, AL, to the shores of Lake Michigan in Gary, IN, the route is packed with detour-worthy stops and destinations worth discovering. With the help of travel expert and author Connie Pearson, we’ve mapped out the ultimate I-65 road trip, highlighting the best places to eat and explore along the way.
Every Exit Tells a Story
Connie’s latest travel guide, Take the Drive on I-65: Where Every Exit Tells a Story, covers all 887.3 miles of the interstate, spotlighting the must-see stops along the route. Made in collaboration with the Alabama Mountain Lakes Tourist Association, it’s got everything you need to know to make the most of this adventure as you cross the U.S. from tip to tail.
“I-65 is so much more than getting from Chicago to the Alabama Gulf Coast,” author Connie Pearson tells us. “Along this highway, there are sites, tastes, activities, and opportunities for practically every type of traveler.”
The book highlights destinations for eight types of travelers, from outdoor lovers to families with kids to shopaholics. It was released just ahead of America’s 250th Anniversary, something that was on Connie’s mind as she put the guide together.
“Not only can you travel ‘from sea to shining sea’ — Lake Michigan to Mobile Bay — you have easy access to significant sites related to five U.S. Presidents, Civil War battlefields, and three state capitals,” she shares.
ALABAMA
Coastal Kickoff: Mobile
We begin our road trip in Mobile, the heart of Alabama’s Gulf Coast, where you can soak up the sun, surf, and history in one of the oldest cities in the country. Enjoy the waterfront views, a walkable downtown (especially the Lower Dauphin Street Historic District), and some of the freshest seafood straight from the Gulf.
Although it’s a popular summer vacation spot, Mobile isn’t just a seasonal destination. “Mobile and the Gulf Coast are heavily populated in the summer but are great for relaxing without the crowds in fall and winter,” Connie says. Plus, it’s worth the trip to experience the birthplace of America’s Mardi Gras!
Must-See Detour: Connie suggests visiting the Bellingrath Gardens & Home and Oakleigh House Museum for a bit of local history. She also recommends dining at some of the many great seafood restaurants on Mobile Causeway (also known as Battleship Parkway). “My favorites are Bluegill Restaurant and Original Oyster House,” she shares.
History Hub: Montgomery
The first state capital on our journey, Montgomery, Alabama, is a must-visit for history buffs. The city is home to several cultural sites, including the Rosa Parks Museum and the Alabama Shakespeare Festival.
Visit Old Alabama Town for a step back in time, or enjoy a river cruise aboard the Harriott II paddle-wheel boat. For more adventurous travelers, Montgomery Whitewater is a unique outdoor destination offering whitewater rafting and tubing, along with ziplines, mountain biking, bouldering, and more.
Must-See Detour: On the way to Montgomery, Connie suggests going a few miles west (Exit 93) to Monroeville, home of To Kill a Mockingbird author, Harper Lee. Even non-literary buffs will appreciate the homage paid to this timeless classic.
Once there, check out the Hank Williams Museum for your country music fix, or The National Memorial for Peace and Justice, which Connie describes as a “shocking and sobering” experience.
Culture and Foodie Stop: Birmingham
Birmingham’s storied history is reason enough for a visit, but the city’s wealth of offerings has a way of surprising first-timers and even repeat visitors. From world-class dining and shopping to vibrant arts and entertainment districts and abundant outdoor recreation offerings, there is no shortage of things to do in the Magic City.
In Birmingham, you’ll find history and culture around every turn. You can learn about the city’s defining role during the Civil Rights Movement at the Civil Rights District, explore the steel boom at the iconic Vulcan Park and Museum (featuring the city’s famous Vulcan statue), or take in the latest exhibits at the Birmingham Museum of Art. And don’t leave without dining at one of the many MICHELIN-recommended restaurants in town.
While the Magic City is certainly worth a stop, beware of Birmingham’s infamous “Malfunction Junction,” where I-65 intersects with I-20 and I-59. This area is home to frequent accidents and can be a major headache for drivers.
Must-See Detour: “Just south of Birmingham near Exit 234, check out Orr Park in Montevallo. Children will love finding the whimsical figures carved into at least 50 cedar trees,” Connie says. “For outstanding pizza, head to Davenport’s Pizza Palace on Cahaba Road in Mountain Brook.”
Arts and Innovation Hub: Huntsville
Connie is an expert on travel in North Alabama, and the second edition of her book, 100 Things to Do in Huntsville and North Alabama Before You Die, is set to be released on August 1. Until then, check out our recommendations for Huntsville, one of the fastest-growing destinations in the state. Not only will you find the U.S. Space and Rocket Center, but you’ll also discover great places to eat and fun things to do in the Rocket City’s vibrant downtown.
There’s always something for art and music fans at Lowe Mill Arts and Entertainment, the largest privately owned arts facility in the country, and the Orion Amphitheater offers a robust schedule of shows and events. The region’s live music scene, network of state parks, and exceptional shopping across small towns and bigger cities make it an I-65 destination to savor and explore.
Must-See Detour: Connie says the Thomas Dambo creation called “Mama Zelda” at the Huntsville Botanical Garden is a must! Another gem is Harrison Brothers Hardware — the perfect place to find a one-of-a-kind souvenir crafted by a local artisan.
TENNESSEE
Southern Charm Excursion: Franklin
The drive from North Alabama into Southern Tennessee is one of the most stunning along all of I-65, thanks to the endless rolling hills set against the distant horizon. And Franklin, Tennessee, just happens to be one of Connie’s favorite destinations along this lovely stretch. “Franklin is a great place for history buffs, shopaholics, music fans, nature lovers, and foodies,” she says. “Plus, you are very likely to spot someone famous when you least expect it.”
Just 20 miles south of Nashville, this small town is one of Tennessee’s most picturesque, thanks to its beautifully preserved, walkable downtown lined with historic buildings and locally owned shops. Community life is just as much a part of Franklin as its history and aesthetic, with seasonal festivals, markets, and events drawing visitors throughout the year.
Must-See Detour: Connie suggests visiting the Factory at Franklin for one of Five Daughters Bakery‘s famous 100-layer donuts before taking a short drive to Leiper’s Fork for shopping.
Music Mecca: Nashville
Tennessee’s capitol city is an obvious destination along I-65. First-timers will want to hit all the high points like the Gaylord Opryland Resort, the Country Music Hall of Fame and Museum, and Honky Tonk Highway, but there’s something new to experience each time you return.
Explore fun Nashville neighborhoods like The Gulch, Wedgewood-Houston, or Sylvan Park, and see how the city reinvents itself on every block.
Of course, live music tops the list of things to do, but Nashville’s thriving arts scene, exciting shopping, and renowned culinary offerings make it one of the most popular spots on our road trip. There’s also plenty for nature lovers to enjoy, whether in one of the city’s iconic parks, greenways, or on the river.
Must-See Detour: Visit The Parthenon and the surrounding Centennial Park, and Connie recommends The Row Kitchen & Pub for live music and great food.
KENTUCKY
Adventure Hub: Bowling Green
Bowling Green is a unique destination with several one-of-a-kind attractions. The beautiful Fountain Square Park, located in the heart of downtown, is the perfect place to start your exploration of the city. Car enthusiasts will love the National Corvette Museum, while locomotive lovers will enjoy the Historic RailPark and Train Museum.
No trip to Bowling Green is complete without paying a visit to Mammoth Cave National Park. On the way, stop by Smiths Grove to soak up its quaint, small-town charm. Shop the day away along the Main Street Historic District and sample craft beverages at Balance Distilling Co. and Bluegrass Vineyard.
Must-See Detour: For a family-fun adventure, Lost River Cave includes an underground boat ride.
Derby Stop: Louisville
Whether you’re excited to visit Louisville for the Derby vibes or bourbon crawls, expect to be surprised by this bustling, ever-evolving city. Sports fans will want to head to the Louisville Slugger Museum and Factory, then to the Muhammad Ali Center.
Bourbon connoisseurs have their pick of big-name and small-batch distilleries to explore. The Evan Williams Bourbon Experience is in the heart of downtown, while the James B. Beam Distillery (home of Jim Beam Bourbon) is a short detour from I-65 just south of the city. Everyone will love spending the afternoon at Waterfront Park and exploring NuLu, the city’s hip and artsy East Market District.
Must-See Detour: Stop by The Derby Cafe & Bourbon Bar at the Kentucky Derby Museum. “In the café, you can sample three iconic Kentucky favorites — a Hot Brown, Derby pie, and a Mint Julep,” Connie says. “At the museum shop, you can buy a hat for your next Derby party.”
INDIANA
Racing Fans and Urbanites Stop: Indianapolis
Connie shares that Indiana came as a surprise on her I-65 road trip. “As someone who has lived all but four years of her life in Alabama, I’m ashamed to admit I had little knowledge of what was only a few hundred miles north,” she says.
While she advises against Southerners going in winter if they aren’t used to the cold, fall in Indiana is beautiful. “I declare that the leaf colors were every bit as stunning as those we had seen in past years in Maine and Vermont,” she shares.
The biggest city along I-65, Indianapolis has no shortage of destination-worthy things to do, from experiencing the Indy 500 in May (or visiting the Indianapolis Motor Speedway Museum any time of year), to serious shopping and perhaps the best steak you’ll ever have at the St. Elmo Steak House.
Drivers, prepare yourselves for “The Spaghetti Bowl” in Indianapolis, a confusing cluster of interstate interchanges and overpasses where I-65 connects to I-70 (also known as the North Split).
Must-See Detour: Don’t skip White River State Park. “It’s comprised of seven major attractions right in the center of the city, including museums, gardens, and a zoo all within walking distance of each other,” Connie explains.
College Town Excursion: Lafayette
Home to Purdue University and nestled on the banks of the Wabash River, Lafayette offers a unique vibe. Dig into the local culture through Purdue’s theater performances and sporting events, take in the exhibits at the Haan Museum of Indiana Art, and shop local at the Lafayette Farmers’ Market.
While the attractions are great, Connie says the food alone is worth the trip. “Hoosiers are kindred spirits of mine in terms of loving sweet treats — candy stores and ice cream parlors in business for generations, the best donut I’ve ever eaten, and signature root beer are just a few of the treasures we found,” she says.
Must-See Detour: Connie recommends visiting Triple XXX Family Restaurant for its famous root beer, made with the same recipe since 1895.
Lakeshore Destination: Gary
The final stop on our road trip, Gary, Indiana, rests on the southern shores of Lake Michigan. Take in the miles of cornfields that line your way along the interstate, which Connie describes as having “their own sort of beauty.”
Once there, the Great Lake is the main attraction, drawing nature lovers, birders, and outdoor enthusiasts of all kinds to its shores.
Marquette Park is a great starting point for exploring the shoreline, with its sprawling dunes, beaches, and lagoons. And no trip to Gary is complete without paying a visit to Michael Jackson’s childhood home. No, you can’t go inside, but it’s worth a stop, nonetheless.
What many people don’t realize is that Chicago is less than an hour around the lake from Gary, so hop on the I-90 if you want to extend your road trip a little further.
“Traveling north from mile marker 184 to 207, you will see a vast number of wind turbines. I was puzzled about that until I realized we were getting closer and closer to the Windy City, and then it made perfect sense,” Connie tells us.
Must-See Detour: Travel east up the shoreline to Indiana Dunes National Park. “You can stand on the shore of Lake Michigan and see the Chicago skyline in the distance,” Connie says.
Ready to plan your own ultimate road trip? Grab a copy of Take the Drive on I-65: Where Every Exit Tells a Story, and get ready to hit the road!
A very special thanks to Connie Pearson for her expertise and photos. Check out her blog, There Goes Connie, for more of her travel insights!
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Katie Leigh Matthews
A Birmingham native, Katie is a lifelong waterfall chaser and is passionate about the outdoors. She also loves connecting with remarkable women in the Birmingham community and bringing their stories to life. Katie has been writing professionally for over six years; you can find more of her work at Moms.com and Islands.com.