Your 2023 Guide to Fall in the Upper Cumberland

From pumpkin patches to Cooking on the Square, there is so much to do in the Upper Cumberland this fall. Fortunately, we have created a list of them all so that you can do your best to take advantage of the changing seasons.

September 30: 5th Annual Upper Cumberland Baby Expo

Looking for resources as a new or expecting parent? Visit Dogwood Park Saturday, September 30, from 9 a.m. to 1 p.m. for the 5th Annual Upper Cumberland Baby expo for the opportunity to meet with a variety of prenatal and postpartum professionals as well as shop from participating vendors. This event will be free for all families to attend.

For more information, visit


September 30 – October 29: Cantrell Farms – Granville, Tennessee

Take advantage of the cooling weather with a trip to Cantrell Farms. This charming plot of land surrounded by the hills of Granville boasts a colorful pumpkin patch, large corn maze, a tire-playground, and so much more. The family farm will be open on the weekends beginning Saturday, September 30 and going until Sunday, October 29.

To learn more, visit

September 30: Bacon Festival – Cookeville, Tennessee 

Bring your appetite to the Hyder Burkes Pavilion on Saturday, September 30 from 10 a.m. to 4 p.m. for Center Hill Event’s Bacon Festival. Savor the last Saturday of September with lots of bacon treats, over a hundred arts and crafts vendors, boutiques, food trucks and a kid’s zone. The event will be free for all to attend.

For more information, visit

September 30: Oktoberfest – Cookeville, Tennessee

Oktoberfest returns to Cookeville! Go to Heavenly Host Lutheran Church for a day of fun complete with homemade German food, Calk Killer Beer, a silent auction, bake sale, and activities for the kids. The funds raised from this event on Saturday, September 30 from 1 to 5 p.m. will benefit Doctors without Borders, Cookeville Pregnancy Clinic, and Operation United Hope.

For more information, visit

777 S Willow Ave., Cookeville, TN 38501

September-October: Muddy Pond Sorghum Mill– Monterey, Tennessee

This Fall, plan a visit to Muddy Pond Sorghum Mill for a truly unique experience. Spend the day in the breathtaking hills of Monterey observing how the Guenther family makes sorghum syrup. The mill will be open to the public every Tuesday, Thursday, and Saturday in September and October. 

To learn more, visit 

October 1 – 31: Scarecrow Festival – Granville Tennessee 

Take a stroll through the town of Granville to experience Tennessee’s largest display of scarecrows, who will be decorated and staged to bring this year’s theme, “Colorful Stories All Around,” to life. The festival will be open from Sunday, October 1 through Tuesday, October 31. Tickets are $7 for adults, $5 for kids ages 6-12, and those 6 and under will be admitted for free.

For more information, visit

October 6: 2023 Fall Marketplace – Red Boiling Springs, Tennessee 

Start the first weekend of October with a trip to A Southern Marketplace’s 2023 Fall Market. Shop over 80 vendors and sample the local goodies spread out throughout the gorgeous, multi-generational Acre of Grace Farms from 10 a.m. to 4 p.m. on Friday, October 6 and Saturday, October 7.

For more information, visit[]%7D.

October 6: Chuckwagon Festival – Cookeville, Tennessee

Step back in time to experience the Wild West at the first annual Chuckwagon Festival. Expect chuckwagon demonstrations, wild west reenactments, cattle roping, hayrides, food trucks, artisan vendors, and more for some old-fashioned family fun at Lazy G Ranch from 10 a.m. to 4 p.m. on Friday, October 6 and Saturday, October 7.

To learn more, visit

October 7: 32nd Annual Great Pumpkin Festival – Allardt, Tennessee 

Celebrate the changing seasons with a fun day in Allardt, Tennessee. Attendees can look forward to the Pumpkin Run, Pumpkin Pie & Roll Contest, Pumpkin Festival Parade, and so much more throughout the entire day.

To check event times and locations, visit

October 6: Classic Cinema at the Depot – Cookeville, Tennessee

This beloved Cookeville tradition will return every Friday night in October, starting at 7 p.m. at the Cookeville Depot Museum. This year’s selection of featured movies will ensure that there is something for every age to enjoy. Admission will be free, and concessions will be $1 each.

For more information, visit

116 West Broad Street

Cookeville, Tennessee 38501

October 7: Oktoberfest at the Silo – Cookeville, TN

Join our friends at Red Silo for Oktoberfest! They will have Oktoberfest beer on tap, music, food, games and fun!

For more information visit

October 13: Rocktober – Monterey, Tennessee

Get ready to rock out with the bands Warrant, Winger, and Firehouse on Friday, October 13 from 6 to 11 p.m. at The Old Gray.

For more information, visit


October 14: Food Truck Festival & Fall Market – Cookeville, Tennessee 

After its great success last year, the 2nd Annual Cookeville Food Truck Festival & Fall Market will return on Saturday, October 14, from 10 a.m. to 5 p.m. at the Putnam County Fairgrounds. Anticipate a fun Fall day with too many food trucks to count, numerous local craft vendors, a kids’ zone, car show, and more. Parking and admission will be free.

For more information, visit


October 14: North Springs Music Festival – Whitleyville, Tennessee 

Spend Saturday, October 14, at an outdoor music festival meant for the whole family. The lineup will feature headliners from various genres, so there will be something for everyone this year at the beautiful Kennedy Farms. The North Springs Music Festival will start at 2 p.m. and go until at least 10 p.m. Prices vary by the type of ticket.

For more information, visit

5779 Jennings Creek Highway

Whitleyville, Tennessee


October 19: Trunk or Treat – Cookeville, Tennessee

Begin the Halloween season with this free event at Cumberland Auto Center from 5:30 to 8:30 p.m. on Thursday, October 19. Grab some family or friends to help you collect tons of candy or goodies provided by over 50 participating local businesses. This and more await!

To learn more, visit

1540 Interstate Drive

Cookeville, Tennessee 38501


October 21: WCTE PBS Haunted Half Marathon – Cookeville, Tennessee

What better way to pass a crisp autumn day than with blues and beer? Come out to Dogwood Park on Saturday, October 21, from 12 to 4 p.m. to sample over a hundred different local, regional, or national craft beers while listening to never ending live blues music and eating from a variety of food truck selections. The money raised from this event will be used to support WCTE PBS which has been serving the Upper Cumberland community for more than 44 years.

For more information, visit


October 27: Upper Cumberland Habitat for Humanity Cooking on the Square – Cookeville, Tennessee

Savor the flavors of the season with the 26th annual Cooking on the Square. Those in attendance on Friday, October 27 from 11 a.m. to 1 p.m. at the courthouse square will be gifted a keepsake bowl to try an assortment of gumbos, jambalaya, and other Cajun themed soups or stews. The money raised through ticket sales will be used to support Upper Cumberland’s Habitat for Humanity. 

For more information, visit


October 28: Halloween Bash – Cookeville, Tennessee

Prepare yourself for a terrifying time at the 1st Annual Upper Cumberland Halloween Bash on Saturday, October 28, from 6 p.m. to midnight at the Cookeville Holiday Inn. This adult-only event will feature a costume and karaoke contest, a cash bar, live DJ, thrilling games, and more. Get full access and a discount on a hotel room with the purchase of a $25 ticket. 

For more information, visit


October 31: Cookeville Treat Trail – Cookeville, Tennessee 

Have some spooky fun on Halloween at Cookeville’s Treat Trail. Don a costume and take a stroll through Dogwood Park to stock up on all sorts of sweet treats. This free event offers the whole family a safe and controlled environment for trick or treating from 4 to 6 p.m.

For more information, visit

30 East Broad Street

Cookeville, Tennessee 38501


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