September To-Do List Along the Backroads
Hometown Headliners
Hernando Town Square, Every Thursday, September 4–25
Spend your Thursday evenings on the square in Hernando, where music fills the air and neighbors gather like family. The Hometown Headliners concert series is the perfect way to ease into fall—bring a lawn chair, grab a bite downtown, and enjoy live performances under the stars.
First Friday Back Porch Party
DeSoto Arts Council – Hernando, MS, September 5
Kick off your weekend with art, music, and community spirit at the DeSoto Arts Council. TheirFirst Friday Back Porch Party is a local tradition that brings creativity and connection together on a laid-back evening in Hernando.
International Goat Days Festival
Ed Haley Sports Complex – Millington, TN, September 6
Quirky, fun, and uniquely Millington—Goat Days is a must-experience event! From goat paradesto family games, music, and food, it’s the kind of festival you’ll talk about long after it’s over.
Go Cat Go Rock ‘n’ Roll Charity Car Show
Living Hope Church – Piperton, TN, September 6
Classic cars meet rock ’n’ roll for a day of fun and fundraising in Piperton. Stroll through rows of vintage rides, enjoy live music, and soak in the nostalgia.
Harleys with Heart Poker Run
Southern Thunder Harley Davidson – Southaven, MS, September 6
Rev your engines for a good cause. The Harleys with Heart Poker Run combines the thrill of the ride with the joy of giving back—an event that brings bikers together for community impact.
Germantown Festival
C.O. Franklin Park – Germantown, TN, September 6–7
One of the region’s most beloved festivals, the Germantown Festival is packed with arts, crafts, rides, food, and family fun. A classic celebration of community that’s worth the drive.
Lauderdale County 4-H Chicken Show & Auction
Lauderdale County Fair Grounds – Halls, TN, September 9
Yes, it’s exactly what it sounds like—and it’s delightful. Celebrate the hard work of local 4-H kids as they showcase and auction their feathered friends. A true small-town gem.
Lauderdale County Fair
Lauderdale County Fair Grounds – Halls, TN, September 9–14
A week of rides, exhibits, contests, and good old-fashioned fair fun. If you’re craving funnel cakes, neon lights, and that unmistakable fairground energy, this is your stop.
Crittenden County Master Gardener Fall Gardening Class
Crittenden County Extension Office – Courthouse Square, Marion, AR, September 11
Gardeners of all levels are invited to learn tips and tricks from the Master Gardeners of Crittenden County. Perfect for anyone ready to get their hands dirty and grow something beautiful this fall.
North Mississippi Hummingbird Festival
Snowden Grove Park – Southaven, MS, September 13
Celebrate the beauty and magic of nature at the Hummingbird Festival, where family-friendly activities, live music, and environmental education come together. A sweet stop for bird lovers and outdoor enthusiasts alike.
Fayette County Cotton Festival
Somerville Square – Somerville, TN, September 13
A beloved annual tradition, the Cotton Festival brings Somerville’s square to life with vendors, food, music, and plenty of small-town charm.
Mid-South Balloon Festival
Corner of TN-57 & Frazier – Rossville, TN, September 20–21
Hot air balloons fill the sky for one of the most colorful weekends of the year. Whether you come for the rides, the views, or just the atmosphere, it’s a backroads highlight you won’t want to miss.
Harvest of Hope
Joyners Camp Ground – Somerville, TN, September 21
This family-friendly festival blends community fellowship, food, and fun in a peaceful outdoor setting.
MidSouth Fair
Landers Center – Southaven, MS, September 25–October 5
A regional tradition for generations, the MidSouth Fair brings big-time rides, midway games, live music, and exhibits to Southaven. This year marks another chance to make memories that last a lifetime.
Covington Heritage Festival
106 West Liberty Avenue – Covington, TN, September 26–29
Step into history and heritage at this Covington favorite. With live music, food, crafts, and community celebration, the Heritage Festival is a true showcase of small-town pride.
Thunder Over Fayette County Air Show
Fayette County Airport – Somerville, TN, September 27
Watch the skies come alive with planes and aerial performances at this exciting air show. It’s an adrenaline-pumping day of thrills and family fun.
Rosemark Country Fair
Rosemark Historic District – Rosemark, TN, September 27
A fair with heart and history, the Rosemark Country Fair is all about celebrating community roots with food, crafts, music, and fun.
Take the Backroads This September
The beauty of the backroads is in the stories—of music echoing through a town square, families gathering at a county fair, or neighbors coming together to celebrate goats, gardens, and everything in between. This September, let curiosity be your guide. Pack up the car, roll down the windows, and see where the road takes you.