PumpkinFest crowd


Oct. 9

Apple and All Things Fall Festival

10 a.m.-4 p.m.

Morning Glory Orchard in Nolensville

If you’re into all things autumn, Oct. 9 isn’t early at all to get going with your fall celebrations. This year, Morning Glory Orchard will host its first Apple and All Things Fall festival on the grounds with help from Nashville Craft BevCo. This family-friendly day will include orchard fresh apples, cider slushies, pumpkins, mums and all sorts of fall goodies including amazing local finds in the orchard store.

Oct. 23

Music Country Grand Prix

12:30 p.m.-6 p.m.

Brownland Farm in Franklin

This event benefits Saddle Up!, which serves Middle Tennessee children and youth with disabilities. The Music Country Grand Prix is an equestrian jumping competition featuring top riders and horses from across the nation that has been going since 1988. The fundraiser has collected more than $2 million since its inception. The day includes tailgating to the side of the show arena and attendees can sponsor VIP cabanas for up to eight guests on the other side.

Oct. 30

36th Annual Pumpkinfest

10 a.m.-7 p.m.

Main Street in Franklin

In 2021, the Heritage Foundation of Williamson County will host the 36th Annual Pumpkinfest, a family fall festival returning this year after a hiatus in 2020. In 2019, more than 65,000 people attended the festival, which stretches along Main Street and its side avenues in downtown Franklin. All of the day’s events are autumn-inspired, including food and drink, children’s activities, live music, costume contests for pets and families, arts and crafts and seasonal gift items. Each year, the Pumpkinfest is hosted by the Downtown Franklin Association, which is a division of the Heritage Foundation. 


Nov. 6

Franklin Parks’ Family Day 

10 a.m.-2 p.m.

Harlinsdale Park in Franklin

Family Day at Harlinsdale Park’s historical farm is free fun for folks of all ages. The festival offers activities like miniature train rides, hay rides, pony rides, a petting zoo and cane pole fishing in the pond. A big hit each year with kids is the touch-a-tractor area, where kids can sit on tractors and operate small excavators. The event will also feature horse-related events this year as well as live music and food for purchase from local vendors. 

20th Anniversary Wine Down Main Street

7 p.m.-10 p.m.

Main Street in Franklin

After taking the kids to Family Day, you can head over to the 20th Anniversary Wine Down Main Street. Attendees will taste wines, shop, listen to live music and sample food from area restaurants from 7-10 p.m. This year Lipman Brothers, Nashville’s oldest and largest distributor of wine and spirits is the official wine sponsor. Proceeds from sponsorships and ticket sales for this event will benefit Boys & Girls Clubs of Middle Tennessee.

Nov. 12-14

Pickin’ Leiper’s Fork

Various hours

Props Antiques in Leiper’s Fork

This free outdoor event is in the village of Leiper’s Fork. At and around Props Antiques, folks can find a selection of vintage items, artisan crafts and antiques as well as live music, food for purchase and more. The event takes place Nov. 12 from noon to 6 p.m.,  Nov. 13 from 9 a.m. to 5 p.m., and Nov. 14 from 9 a.m. to 5 p.m. (Don’t miss the small batch candies and chocolates at Props Antiques.)

Nov. 20

Franklin Makers Market: Holiday Market

11 a.m.-4 p.m.

Westhaven Lakefront in Franklin

Just ahead of the Thanksgiving holiday, check out this free, family-friendly holiday market at Westhaven Lakefront. This winter market includes more than 50 craft and artisans vendors, tasty treats, kids activities, a photo booth, a cocktail bar and more. Franklin Makers Market  bills itself as the best place to find unique holiday treasures for your family and friends while supporting local makers and small businesses from all of the Middle Tennessee area. 


Dec. 4

Morning with Santa

9 a.m.-noon

John P. Holt Brentwood Library in Brentwood

Gather the kids, make sure their wish lists are updated and head over to the Brentwood Library to meet with the big man himself. For this 30th edition of Morning with Santa, he’ll be at the library from 9 a.m. to noon. The library will also have a few games and more. It’s the perfect thing to do before hitting up the Christmas parade in Franklin. Ask him for the gifts and then go see if he makes it to the parade with his reindeer on time. 

Franklin Kiwanis Christmas Parade

2 p.m.

Historic Downtown Franklin

The Kiwanis Club of Historic Downtown Franklin is making its return following its cancellation in 2020 due to COVID-19 concerns. Registration to participate in the parade is open on Eventbrite: Search for 2021 Franklin Kiwanis Christmas Parade. The theme of this year’s parade is Songs of the Season. The Franklin Kiwanis Christmas Parade is the primary fundraiser for the Kiwanis Club of Historic Downtown Franklin. Through sponsorships by businesses and individuals, dollars are raised which are then used to grant $1,000 scholarships to local graduating seniors. A number of social service agencies that serve children have also received monetary donations from the club, which supports the mission of Kiwanis — “to serve the needs of children.” Those who would like to become a sponsor of the parade can contact the club at [email protected] or call (309)261-3500.  

Dec. 10

Flashlight Candy Cane Hunt


Eastern Flank Battlefield Park in Franklin

The grounds of Eastern Flank Battlefield Park will be sprinkled with candy canes ready to be eaten and then attendees will grab their flashlight to help hunt for the holiday treats. Kids will decorate treat bags for candy canes before the hunt. Hot chocolate and cookies will be served. Participants must bring a flashlight, and all other supplies will be provided. Festive outfits are encouraged. This event is limited to 100 participants and pre-registration is required. The event fee is $5 per person, including adults, and begins Nov. 8.

Dec. 11-12

36th Annual Dickens of a Christmas

10 a.m.-6 p.m.

Historic Downtown Franklin

The Heritage Foundation of Williamson County’s 36th Annual Dickens of a Christmas is Middle Tennessee’s largest outdoor Christmas festival, returning this year after a pause in 2020. The festival recreates the time of Charles Dickens using historic downtown Franklin’s charming architecture as the backdrop. A variety of musicians, dancers and Dickens characters will fill the streets. Expect to see and interact with the nefarious Fagin from Oliver Twist; Jacob Marley, Ebenezer Scrooge, Tiny Tim and the rest of the Cratchit family from A Christmas Carol; and of course, a Victorian Father and Mother Christmas with treats for children.

Date To Be Announced

Spring Hill Santa Ride

The Well in Spring Hill

Nonprofit The Well’s executive director, Shelly Sassen, and her husband, Tim, started a new annual tradition in 2019 in Spring Hill: Participants decorate their bicycles with antlers, wreaths, and any other holiday-themed decorations they could get their hands on for a Spring Hill Santa Ride. Last year, more than a dozen riders took to the streets heading west on Duplex Road before heading north on Miles Johnson Parkway, making a quick stop at the Morning Pointe assisted living home to sing a few Christmas carols, singing such classics as “Jingle Bells,” “We Wish You a Merry Christmas” and “Santa Claus Is Comin’ to Town.” Then they departed northbound and riders then linked up with Main Street where the occasional supportive car honk could be heard. Riders made their final stop at Grecian Family Restaurant off of Main Street for a mid-ride lunch before ultimately heading back to their point of origin. What fun it is to ride.