With the first day of fall just around the corner (Sept. 22), events season in Williamson County is already off to a rousing start.

From annual traditions like Pumpkinfest to newer ones like Oktoberfest in Thompson’s Station, here are some old and new events you won’t want to miss this autumn.

Pilgrimage Festival

Last year, Justin Timberlake was joined by Chris and Morgane Stapleton on stage./Brooke Wanser

Fall kicks off this weekend for those making the pilgrimage to Harlinsdale Farm to see Lionel Richie, Jack White, Dave Matthews, Chris Stapleton and more at the fourth Pilgrimage Festival. Tickets are still available, but if you aren’t willing to drop that much change, local artists will perform at various venues in downtown Franklin beginning Friday afternoon.

When: Sept. 22-23
Where: Harlinsdale Farm, Franklin

Oktoberfest at Homestead Manor

For the first year, historic Homestead Manor will get in on the fall fun with an Oktoberfest celebration. Forty local breweries will provide libations for tasting, and Bavarian food and beer-inspired ice cream from Hattie Jane’s will also be available during the traditional German event. Prost!

When: Saturday, Oct. 6, 5 to 9 p.m.
Where: Homestead Manor, Thompson’s Station

Rippavilla Blues & Jazz Festival

Another new event is coming to Spring Hill’s Rippavilla Plantation this fall; a free jazz and blues festival! Beer on tap and bites from food trucks will be available for purchase.

When: Saturday, Oct. 27, 4 to 9 p.m.
Where: Rippavilla Plantation, Spring Hill

Gentry’s Farm

A family tradition for many, beloved Coach Jimmy Gentry opens his farm to the public each fall for pumpkin picking. A cornfield maze will delight children, as will a tour of the historic working farm by wagon ride to see the cows.

When: Saturday, Sunday, Monday (limited hours)
Where: Gentry Farms, 1974 New Highway 96 West, Franklin


Hosted each year by the Heritage Foundation, the 35th annual Pumpkinfest comes at peak fall foliage time in Middle Tennessee. Local vendors will line the streets of downtown Franklin for this free event. Costume contests, arts and crafts and a kids zone will keep children occupied, while pumpkin carving and food and beer might satisfy older attendees.

When: Saturday, Oct. 27, 10 a.m. to 6 p.m.
Where: Downtown Franklin

Grave Matters Tour
Wanting to get in the Halloween mood? Check out this nighttime cemetery tour, where reenactors will bring the dead to life with stories from the Civil War.

When: Various dates, 7 – 9 p.m.
Where:  4th Avenue North and North Margin Street


Bootlegger’s Bash

Patrons mingled in the garden outside Carnton at the 2017 Bootlegger’s Bash./Brooke Wanser

For the eighth year, this whiskey tasting event will take place in the garden at Carnton. Hosted by the Battle of Franklin Trust, patrons can interact with local distillers and makers, before enjoying a catered dinner and live music and dancing in the historic setting. The perfect au revoir to summer!

When: Friday, Sept. 28, 6:30 p.m.
Where: Carnton Plantation, Franklin

Take in a high school football game

From top-ranked Brentwood and Ravenwood High Schools to Brentwood Academy, there’s no shortage of talented football teams in Williamson County. Home Page Sports Editor recommends Nolensville as an up-and-coming team, and calls Independence High’s the most enjoyable offense to check out. Bask under your favorite school’s Friday night lights, or join a friend for a tailgate at least once this season.

When: Friday nights at 7 p.m.

Veteran’s Day parade

A flag suspended above Main Street greeted parade watchers in 2017./Brooke Wanser

This annual event honors veterans and active duty military with a patriotic parade through the heart of historic downtown Franklin. Bring your fold up chair and come early to people watch; this is a big one!

When: Saturday, Nov. 10, 11 a.m.
Where: Main Street, downtown Franklin