7 Perfect Fall Weekend Activities in Franklin

The dogwoods are tinged with crimson, which means it’s October in Franklin – arguably the best month of the entire year… crisp blue skies, low humidity, pumpkin spice, everything, and all the fall fun you can handle!

Gentry Farm

Autumn weekends in Williamson County abound with opportunities to get outside and soak up the harvest season’s best local traditions. There’s no better place to start than on a Century Farm. The seventh-generation Gentry Farm is only open to the public a few days a year. Still, it’s worth the wait – pick-your-own pumpkins, a four-acre corn maze, tire swings, hayrides, a petting zoo, and engaging, hands-on displays and games featuring farm history make for a delightful day for kids and adults alike.

Arrington Vineyards

Fair warning: driving through the hills of Williamson County, the beauty of the season is going to beg you to keep exploring. Fortunately, the communities dotting our landscape are eager to welcome you. At Arrington Vineyards, weekends start with Food Truck Fridays and progress into Jazz on the Hillside and Bluegrass in the Barn. Bring your picnic or purchase on-site, alongside a broad selection of award-winning wines.

Leiper’s Fork

In Leiper’s Fork, located just off the scenic Natchez Trace Parkway, slow down and spend a few hours among the antique shops and art galleries, guitar picking, and fire pits. This little village is jammed with local flavor, and restaurants serve everything from made-to-order breakfast at the Country Boy to Puckett’s Grocery’s pit barbecue, burgers, and deli sandwiches. The upscale menu at 1892 is equally impressive.

Franklin Walking Tours

Back in Franklin, Main Street is the place to start. It’s never too early to be thinking about the holidays as you browse the dozens of boutiques, shops, and showcases that comprise our historic core. Take in the architecture, or better yet, take a tour! Check out Franklin on Foot and Franklin Walking Tours for a diverse set of options ranging from neighborhoods and Insta-worthy photo sites to historic cemeteries, ghost tours, and Murder and Mayhem. This town hasn’t always been so squeaky clean, and our resident experts are eager to share the stories.

The Franklin Theatre

Don’t miss the Franklin Theatre; a 300-seat fully restored 1937-era theater that brings in world-class recording artists and offers classic movies and other incredible programming. On October 29 and 30, Spooktacular will take the stage, a New York City-based troupe of renowned acrobats that promises to put on a spine-tingling circus performance.

Franklin Pumpkin Fest

That weekend will be a big one in downtown Franklin – the 36th Annual PumpkinFest returns on Saturday, October 30, with all of its autumn-inspired food, vendors, and entertainment. Hosted by the Downtown Franklin Association, the festival stretches along Main Street and its side avenues. On Sunday, as the sun sets, Halloween in Hincheyville takes over two of Franklin’s historic residential blocks on West Main and Fair Streets. Streets are closed, and homeowners go all-out with decorations and trick-or-treating.

And while you’re exploring our National Register districts and landmarks, the perfect way to begin is with a Visit Franklin Digital Passport. Whether your interest is food and drink or architecture and history – or you’re looking for great photos or a fun scavenger hunt – the eight passports offer self-guided walking and driving tours guaranteed to entertain. Complete the journey and return to the Visitors Center on Fourth Avenue North for a free prize! 

With all that Franklin and Williamson County have to discover, each season provides its stunning backdrop. But there’s just something about October, a special kind of magic that will leave you smiling like a Jack-O’-Lantern.