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The Ultimate Franklin Fall Bucket List

The Ultimate Franklin Fall Bucket List

Although Franklin is special at any time of year, I think the town is at its best in the fall. The crisp weather, vibrant blue skies, autumn leaves, and harvest decorations make walking through the town feel as if you’ve stepped into the pages of Southern Living.

Driving down the country roads outside Franklin, the red, orange, and gold-hued hills of Williamson County will leave you absolutely speechless. 

It’s no wonder, then, that there are plenty of fall-themed activities for couples and families in Franklin over the next few months. Here are some of our favorites. 

Pumpkinfest

Did you know Middle Tennessee’s largest family fall festival takes place in downtown Franklin? The 36th annual Pumpkinfest will take place on Saturday, October 30th this year.

On that day, tens of thousands of people will flock to Main Street to enjoy seasonally inspired food and drinks, arts and crafts, and entertainment. This is one bustling festival you don’t want to miss!

Gentry’s Farm

For many Franklin families, visiting Gentry’s Farm in the fall is a rite of passage. The seventh-generation farm just a few minutes from downtown opens to the public every weekend in October. It offers hayrides, pumpkin picking, a cornfield maze, and lots of outdoor activities for kids.

The Natchez Trace Parkway

When Middle Tennesseans want to see fall color, they head straight for the Natchez Trace Parkway. This 444-mile, federally protected road runs from Nashville to Natchez, Mississippi, and one of its most beautiful stretches cuts right through Williamson County.

Hop on in Franklin at the award-winning Double Arch Bridge at milepost 438 for breathtaking views of Tennessee hardwoods, and continue down the roadway for a few minutes or a few hours — There’s plenty to see and do along the way.

Leiper’s Fork


Just a few minutes’ drive from Franklin, you’ll find Leiper’s Fork, a pint-sized historic village brimming with Southern charm — and fall is my favorite time for a visit.

This is one town where you literally can’t go wrong, no matter which of its businesses you decide to check out. Every one of its handful of restaurants is delicious, and every shop is exquisitely curated. Leiper’s Fork is an unforgettable way to spend an autumn afternoon.

Apple and All Things Fall Festival at Morning Glory Orchard

Looking for something new? This year, Nolensville’s popular Morning Glory Orchard is partnering with Nashville Craft BevCo to launch its first annual apple festival on Saturday, October 9th.

Choose from an assortment of orchard-fresh apples, sip on a cider slushie, pick out pumpkins and mums for your front porch, and browse fresh baked goods, local honey and jams, and other seasonal products in the farm store.

Wine Down Main Street

Adults will want to mark their calendars for the 20th annual Wine Down Main Street Saturday, November 6th, from 7-10 p.m., one of Franklin’s most popular yearly events.

Head to Main Street to taste wines, shop, sample food from local restaurants, and enjoy live music. And if you truly want a big night out, opt for the VIP experience — You’ll be treated to a private food and wine-tasting event in the Franklin Theatre. Proceeds from all tickets benefit the Boys & Girls Clubs of Middle Tennessee. 

Scenic Drives

I’ve traveled far and wide and can tell you with confidence that Williamson County has some of the most beautiful scenic backroads in America — and the best time to enjoy them is in the fall.

From century-old barns to covered bridges to stone walls built during the Civil War era, there’s so much to see on Franklin’s country roads. Check out a list of all my favorite scenic drives here — Several of these are local favorites, and you won’t find them listed anywhere else!

Bootlegger’s Bash

Once upon a time, Tennessee was known for its bootleggers — Leave it to Franklin to celebrate them! The annual Bootlegger’s Bash will happen Friday, September 24th, and include a traditional Southern dinner, live entertainment featuring a dueling piano team, and spirit tastings from several local distilleries, vineyards, and breweries.

All proceeds benefit the Battle of Franklin Trust and the preservation of Carnton and the Carter House. You can buy your tickets in advance at the BOFT website.

Pilgrimage Music Festival

Yes, Bonnaroo was canceled due to flooding, but the good news is Pilgrimage is still coming to Franklin’s Park at Harlinsdale Farm on September 25-26.

Featuring the Dave Matthews Band, The Black Keys, Maren Morris, and Cage the Elephant, among many others, this music festival promises to be amazing. It comes at the perfect time of year weather-wise.

Steaming Fall Beverages

Nothing says autumn like a seasonal coffee drink, and Franklin has some of the best cafes in the state where you can enjoy them.

Sit back and savor a Sweater Weather Latte on the front porch swing at the Coffee House at Second and Bridge in downtown Franklin, or boost your work productivity with a cinnamon-spiced Roosevelt Latte at The Factory’s Honest Coffee Roasters. No matter where you go in Franklin, you’ll find a coffeehouse nearby ready to serve up your favorite hot fall beverage.

Oktoberfest at Mill Creek Brewing Company

Head to Nolensville’s Mill Creek Brewing Company on Saturday, October second, for its annual Oktoberfest celebration, featuring live music from LynnMarie and The Nashville Polka Guys.

This is a family-friendly event, so feel free to bring the whole crew out for some German-inspired October food, drinks, music, and fun.

Franklin Farmers’ Market

For all your harvest-inspired recipes, head to Franklin Farmers’ Market on any autumn Saturday for local produce, baked goods, food trucks, and arts and crafts.

This year-round market always has lots of fabulous Tennessee products to choose from, and we visit often. You’ll find it outside The Factory on Saturdays, rain or shine.

Franklin Digital Passports

One cool new way to see Franklin this fall is with a free digital passport. Choose from one of eight self-guided passport tours (Haunts & Headstones is a good one for October!), sign up to access it on your phone, and enjoy exploring.

Once you’ve finished the tour, you can pick up a prize for completion at the visitor center in downtown Franklin.

Timberland Park

Enjoy the changing leaves on a walk-in rustic Timberland Park, located on the Natchez Trace Parkway in Franklin. All the hikes here are lovely, but I especially recommend the 2.5 mile Big East Fork Reserve loop trail, which includes a hilly forest, a beautiful meadow, a large pond, and other surprises.

Be sure to pick up a map at the Visitor Center before you set off on the trails to avoid getting turned around.

Owl’s Hill Nature Sanctuary

This gorgeous 300-acre nature sanctuary offers lots of family-friendly events in the fall. From Owl Prowls and guided fall color hikes to family campouts and special presentations on everything from bats to mushrooms, there are plenty of fun things to choose from over the next few months at Owl’s Hill Nature Sanctuary.

Once you visit, you will definitely be planning a return trip!

Lucky Ladd Farms

Families won’t want to miss a visit to Lucky Ladd Farms this fall — Billed as an ‘Ag-venture Farm Fun Park,’ fall is the most festive time to experience it.

Lucky Ladd includes a pumpkin patch, a corn maze, sunflower fields in late September, a petting zoo, pony rides, and much more. It’s open Thursdays through Sundays this fall from September 18 through October 30.

Looking for more? Check out the Fall 2021 Guide here for trip itinerary ideas, more fall activities, and more!

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