Your 2022 Guide to Fall in the Upper Cumberland

From pumpkin patches, to music, fun and apple festivals, to trunk and trick or treats, we are providing you with a guide to all things FALL in the Upper Cumberland.

September 9- 10: Cityscape’s 26th Annual Fall FunFest – Cookeville, TN

Welcome to Fall FunFest, Cookeville’s Main Street festival. Join us as we celebrate our 26th year of live music, a variety of arts and craft vendors, delicious food, and family fun. The fun awaits at CityScape’s Fall FunFest, September 9 and 10, 2022. We’ll see you on the Square! 

For more information, visit http://fallfunfest.com/.


September 10th – October 29th: Muddy Pond Sorghum, Monterey, TN

Deep in the hills of Tennessee, midway between Nashville and Knoxville lies a little community called Muddy Pond. During September and October, you can smell the aroma of freshly made sorghum syrup being made by the Guenther family. Stop by the Muddy Pond Sorghum Mill and watch step by step as sorghum syrup is being made.

Muddy Pond Sorghum Mill is in Operation and Open, Saturday before Labor Day, Labor Day (Monday). Closed Tuesday (the next day after Labor Day). After that we are in Operation and Open every Tuesday, Thursday, and Saturday in September and October.

For more information, visit https://www.muddypondsorghum.com/.


September 17th: Cookeville Cemetery Walk – Cookeville, TN

Join us at Cookeville City Cemetery as “residents” tell their stories. Meet with your group and walking guide behind the cemetery office at 241 S. Walnut Ave. to begin. Visit with some of Cookeville’s dearly departed and hear the stories of their lives while seated next to their graves.

The audience can expect to enjoy an evening filled with wonderful historical storytelling!

Tickets are on sale for $15 each at the Cookeville Performing Arts box office or at cpactn.com. Call the Cookeville History Museum at 931-520-5455 for more info.


September 17th: UC Hispanic Heritage Festival – Cookeville, TN

Join us in celebration and appreciation of the diverse Arts, Music, Food, Dance & Cultures of the many Spanish speaking Latino & Hispanic populations.

There will be cultural booths, musical performances, interactive dance demonstrations, ethnic cuisine samples, cultural arts & artists and lots of activities for your family and friends.

The festival will be from 11am until 4pm. Admission is free.


September 17-18: 2nd Annual Great Pumpkin Festival – Cookeville, TN

It’s the season of the PUMPKIN! Join us as we celebrate FALL with CHARLIE BROWN & SNOOPY from Peanuts! The Great Pumpkin Festival will be held on Saturday September 17th 10am – 7pm and 18th (Sunday) 10-4pm in Cookeville, TN at the Putnam county fairgrounds.

Bring the kids to see Charlie Brown and Snoopy as they pick a pumpkin in the great pumpkin patch! We also have free pumpkin painting if the kids want to paint their pumpkins! Then enjoy some shopping with over 100 amazing vendors. Find some beautiful handcrafted or handpicked items! You’ll find pumpkin spice everything! Plus, let the kids get their face painted and play some games! Ready for some true tastes of the South? The hickory smoked aroma of BBQ, hamburgers, hotdogs, quesadillas, nachos, fried oreos, funnel cakes, kettle corn, fried apple pies, apple cider, shaved ice, loaded teas, hot chocolate and more. 

$2 Admission – all proceeds donated to the Putnam county Veterans Hall.


September 23rd – 25th: Northfield Vineyard’s Fall Market – Sparta, TN

Fall Market is back with 60+ vendors, food, music and more! Free admission and free parking!

For more information, visit https://www.facebook.com/events/352873656751743.


September 24th: First UPC Family Fun Fest

Everyone is welcome! Enjoy a time of fun with free bounce houses, live music, corn hole, face painting, food, snow cones, cotton candy, giveaways and more!


September 24th: Heavenly Host Lutheran Church Oktoberfest

Enjoy great German food and Calfkiller beer! Brats, hot dogs, specialty dishes and Coca-Cola products. Join us for a silent auction, bake sale, balloon artist, DJ music, dancing and merriment! Come and bring your friends! From 1pm – 5pm.

$12: Adults

$6: Children 4-10

Free: Kids under 4


September 24th: Baxter Harvest Festival – Baxter, TN

Join us for the Baxter Harvest Festival! Saturday, September 24th 10am-4pm. 

Arts & Crafts
Live Music
Car Show
Helicopter Rides
Kids Area 
and Food!


September 24th – 25th: Homesteads Apple Festival – Crossville, TN

Make plans to join us for the 19th Annual Homesteads Apple Festival! $5 admission for the entire weekend, kids 10 & under are free and free parking! Crafters, antiques, local artists & authors, petting zoo, live music, tons of food & lots of fun activities for the kids! And of course…..plenty of apple-themed food & drinks!! Contact us at the Tower Museum if you are interested in participating as a vendor or sponsor! 931-456-9663
Saturday, Sept 24th (9am-5pm)
Sunday, Sept 25th (9am-4pm)

For more information, visit https://www.facebook.com/events/679956219794743


September 24th – October 31st: Cedarwood Pumpkin Patch – McMinnville, TN

We are so excited to be going into our 22nd season! Pick your own pumpkin, make your way through our mazes, jump on the jump pad, enjoy some live music and a bonfire by the pond, slide down our new 100ft super slide, and much much more!
Our many activities are spread out across our beautiful farm. Making Cedarwood the perfect place for birthday parties, field trips, or just come out with your family and friends to enjoy the farm!

Visit http://cedarwoodfarmstn.com for more information.


September 24th: Dogpalooza – Cookeville, TN

Dog lovers it’s that time of the year . A day full of fun for dogs and people who love them. Cookeville Leisure Services is excited to present the annual Dogapalooza at Cane Creek Dog Park on Saturday, September 24 from 10am – 1pm.  A fun event for citizens and their pets! We look forward to a day full of tail wags and smiles!


September 24th – November 6th: Fall Farm Adventure at Amazin’ Acres – Sparta, TN

Amazin’ Acres of Fun has the largest you pick pumpkin patch in middle Tennessee! We grow all sizes, shapes, and colors of pumpkins that can be purchased at the farm market. We also have corn shocks, gourds, and ornamentals so come see us for all your fall decorating needs!

With a paid farm admission we offer a hayride to pick the perfect pumpkin fresh off the vine. 

We grow our produce with good stewardship practices that provide safe and wholesome products everyone can enjoy, along with great customer service!

Opening Date: September 25th

Closing Date:  November 6th 2:00p.m. – 5:00 p.m.

September Hours:  Saturdays 10:00 a.m. – 7:00 p.m.

                               Sundays 1:30 p.m. – 7:00 p.m.

October Hours:  Saturdays 10:00 a.m. – 7:00 p.m.

                            Sundays     1:30 p.m. – 7:00 p.m.

Fall Break Hours:  October 14 &15, 10:00 – 2:00

November Hours: Saturday, November 6th: 10:00 a.m. – 2:00 p.m.

Visit https://www.amazinacres.com/farm-adventures/ for more info.


September 25th: St. Thomas Aquinas Church’s FALL FESTIVAL – Cookeville, TN

Join us for Saint Thomas Aquinas Catholic Church Fall Festival on Sunday, September 25, 2022 – 9:00 am to 4:00 pm!! Our Fall Festival has always been reputed to have the best ethnic foods due to the diversity of our parish members. There will be Hispanic, Guatemalan, Mexican, Cuban, Brazilian, Polish and American foods featured, in addition to funnel fries and the unforgettable fruit fresca drinks. Carryout containers will also be provided! Magic show performance by Las Vegas quality showman / Comedian act / Live music / Children’s games including water slide events / Crafts and arts / Purchase a chance to win a Variety of Baskets. All age groups are welcome! Mark your calendar to attend our community event with your friends and family!!


September 30th – Whiskey Festival

The annual Cookeville Whiskey Festival in is scheduled for Friday Sept. 30, 2022.

Now in its fifth year, the Whiskey Fest has grown to include vendors representing
hundreds of brands and varieties of whiskey, scotch and bourbon.

Guests will enjoy tasting samples including brands including Pappy Van Winkle, Basil Hayden’s,
E.H. Taylor, Elmer T Lee, George T Stagg, Lagavulin, Old Forester, Thomas H Handy, Stagg,
William Larue Weller and dozens of other fine brands. The festival will be held from 5:30-8:30 P.M. at SaltBox Inn and Stables, 537 Hutcheson Rd in Cookeville. The tasting event will also include wonderful food selections including ahi tuna, prime rib bites, egg rolls, naan, chicken tikka kababs and many other tasty treats.

Whiskey tasting tickets are $100 per person in advance. Designated driver tickets are also
available for $50. No one under the age of 21 will be allowed entrance. Guests are asked to
bring a photo I.D. to the event. Proceeds will benefit the Cookeville Regional Charitable
Foundation Pediatric Programs. Tickets are online at https://cookevilleregionalcharity.org/events/ or call 931-783-2003.


October 1st – 29th: Fall Celebration – Granville, TN

Tennessee’s largest display of scarecrows with hundreds of scarecrows on display. Walk through town and see how this year’s theme, “Colorful Stories All Around”, comes to life. Daily tour tickets are $7.00 for Adults; $5.00 for children ages 6-12 and under 6 are Free.

Find tickets at https://www.granvilletn.com/events/scarecrow-festival-october-1-31-2.


October 1st – 30th: Cantrell Farms – Granville, TN

OCTOBER BEGINNING ON 10/1, WE WILL BE OPEN SATURDAYS 10AM-6PM & SUNDAYS 12PM-6PM

Pumpkin Patch, Corn Maze, Tire Playground, Corn Pit, Trike Track, Farm Animals, Food and Drinks, And More!

Visit https://www.facebook.com/cantrellfarmstn for more info.


October 1st: Allardt Pumpkin Festival – Allardt, TN

Annual festival the first Saturday in October celebrating giant pumpkins. The event features a weigh-off, craft and food vendors, entertainment, a tractor show, and a 3 pm. parade. For more information, visit https://www.facebook.com/allardtfestival.

October 7th – 8th: The American Made Music Festival – Gainesboro, TN

The Jackson County Chamber of Commerce in conjunction with Dailey & Vincent is proud to present Dailey & Vincent’s American Made Music Festival on October 7th and 8th, 2022.

The music festival will be held outside on the Jackson County Airport grounds and offers unforgettable views with the airport nestled in the Tennessee hills right on the banks of the Cumberland River. This 2-day festival, presented by Springer Mountain Farms, features an amazing lineup of hit music from country, bluegrass, and gospel artists, Josh Turner, Shenandoah, Dailey & Vincent, Gene Watson, The Isaacs, A Salute to the Grand Ole Opry, and more artists to be announced.

For more information, visit https://www.americanmademusicfestivals.com.


October 8th: A Southern Sip + Shop Tour

Tour the Upper Cumberland presents: A Southern Sip + Shop Tour

There’s nothing like some Saturday sippin’ and shoppin’ in the South, especially in the Fall!

We’ll take you away for a relaxing winery & vineyard tour, plus tasting at DelMonaco Winery & Vineyards. Then, we will go from sippin’ to shoppin’ as we travel from Baxter to Red Boiling Springs for a sophisticated Southern barn sale with more than 70 hand-selected vendors and artisans, live entertainment, farm tours and more.

Your ticket includes:

– Full-day, roundtrip transportation + designated driver
– Complimentary on-bus beverage
– Tour and tasting with the winemaker at Delmonaco Winery + Vineyards (He’s one of our faves!)
– Admission to A Southern Marketplace Barn Sale
– Take a peek at a recap of our trip to the Spring event, as well as photos from the trip.

Boarding Location:– Sam’s Club, 1177 Sams St, Cookeville, TN 38506.
(Park in spaces adjacent to Sams Street, near the fuel center).

Check-in/Boarding: 10:00 a.m. CT – Photo I.D. will be required upon check-in. Must be 21 and over to participate.

Departure Time: 10:10 a.m. CT

Return Time: 4:30 / 4:45 p.m. p.m. CT

Visit https://tourtheuc.com/sipshop10082022/ for tickets.


October 10th- 11th: Spectacular Circus – Cookeville, TN

For generations, the Carden International Circus Spectacular has merrily rolled the rings of their three-ring circus across the continent, stopping for more than a few performances along the way. Each show is different—acts come and go, and advances in clown-car technology are dutifully adopted—but some things never change: expect to encounter the boundless charms of a dynamic ringmaster and awes from a cast that includes a pack of daring acrobats, bewildering contortionists, a human cannonball, and more than a few show-stopping animals such as liberty horses.

Find Tickets at https://tickets.spectacularcircus.com/event/cookeville-tn—630pm—101022—monday.


October 14th – 16th: Upper Cumberland Air Fare – Sparta, TN

Airshows, Drone Displays, a 5k, Hot Air Balloon and Airplane Rides, Food Trucks, Vendors, Military Aircraft Displays, Warbirds, and Exotic Cars are just a few of the things you can see and experience at the 2nd Annual Upper Cumberland Air Fair! October 14-16, 2022 at the Upper Cumberland Regional Airport. Parking is free, Tickets are available in advance and at the gate. Adult admission is $20 in advance, $25 at the gate. Kids 10 and under are free for event admission.


October 15th: WCTE PBS Haunted Half Marathon – Cookeville, TN

In partnership with Run the Cumberland, take part in this Halloween-themed race around Cookeville. The race starts and finishes at Tennessee Tech University campus. All Haunted Half-Marathon runners will receive a race medal and long-sleeved shirt. Registration is now open. For more information on online registration, racecourse details, visit WCTE Central TN PBS website.


October 15th: WCTE PBS Blues & Brews – Cookeville, TN

The Blues and Brews Craft Beer Festival is the Upper Cumberland’s premier fall event that raisesmoney for WCTE PBS!  The 2022 Event will be held October 15th in Dogwood Park in Cookeville, Tennessee from Noon to 4 PM!  This year’s event will feature over 100+ craft beers from local, regionaland national breweries!  All ticket holders will receive a commemorative glass, enjoy all day live bluesmusic, and have access to a variety of food truck selections.  Consider getting a VIP ticket for the daywhich allows you to receive early entry into the event, a commemorative glass, and special access tothe VIP tent with all day complementary food, snacks, and drinks.  Make this year’s Blues and Brews abucket list must-do in 2022!  WCTE PBS has been serving the Upper Cumberland for over 44 years, andwith your purchase, WCTE PBS will continue to be able to bring many educational and engagementservices and local and national programming that we’ve all grown to love.

https://wcte.ticketspice.com/wcte-pbs-blues-and-brews-craft-beer-festival


October 20th: Trunk or Treat – Cookeville, TN

Cumberland Auto Center and Overdrive USA will be hosting its annual Truck or Treat celebration on Thursday, October 20th from 5:30-8:30 pm. This event is open to the public and free of charge. We are asking that participants bring a nonperishable food item that we will donate to families in need here in the Cookeville area. We will have bounce houses, trick or treating, costume contests, and much more. If you should have any questions please call us at 931-520-4128.
We will have a limited amount of Fast Passes Available this year.


October 22nd: Fall Spooktacular – Cookeville, TN

Trunk or Treat Spooktacular Event Bring the family out for a day of fun at Clayton Homes of Cookeville! We will have a trunk or treat, inflatables, and games for the kids!


October 22nd & 29th: Ghostly Gathering – Rugby, TN

Historic Rugby presents Ghostly Gathering on two Saturdays, October 22 and 29, from 5:30 p.m. to 9:30 p.m. Eastern. This yearly Halloween-season celebration frequently sells out! 👀 Ticket link will be up in the upcoming weeks so keep your eyes peeled! Students are for $15, and $25 for adults.

This event is a favorite among village visitors, who enjoy a homemade chili dinner with dessert, followed by oil lamp tours of several historic buildings featuring the “Rugby Edged in Black” exhibit. During the tour, guests meet the “ghosts” of some of Rugby’s earliest residents and hear their stories. Edged in Black offers a look at the death and mourning customs of the Victorian era through the death of Margaret Hughes. The event concludes with a storyteller spinning more spooky stories in the crisp fall air.

Don’t miss this spooky scary event happening in our picturesque Victorian village!

For more information, visit https://www.facebook.com/historicrugby.

October 28th: UC Habitat’s Cooking on the Square – Cookeville, TN

We’re back with Cookeville’s Signature event on the square featuring all you can eat Cajun cuisine!
All proceeds from this event will build an affordable home for a local family in need, giving them the chance to purchase a home built by YOU!

For tickets, visit https://www.uchabitat.org.


October 29th: Cookeville Food Truck Festival & Fall Market – Cookeville, TN

Join us for the 1st Annual Cookeville Food Festival and Fall Market at the Putnam County Fair Grounds on October 29th, 2022 from 10am to 5pm.


October 29th: Halloween Bash – Gainesboro, TN


October 29th: Algood Fall Fest – Algood, TN


October 31st: Cookeville Treat Trail, Cookeville, TN

The Cookeville Treat Trail is back at Dogwood Park for 2022!

Visit Dogwood Park for a free family trick or treating event hosted by Hip Cookeville and Cookeville Leisure Services and sponsored by local businesses!

Costumed trailblazers are welcome to trick-or-treat booths along the Park Path, and enjoy games and other fun activities including a themed photo opportunity.

This event is free to attend.

Be sure to wear your spookiest or cutest costume and enjoy trick or treating with your community.

This event begins at 4:00 and lasts until 6:00. The line will be cut off at 5:30, so be sure to arrive on time.


October 31st: FALL FESTIVAL – Monterey, TN

Monterey First Baptist Church, Monterey United Methodist Church and Monterey Church of the Nazarene. First Baptist will have games, free food and candy. Methodist and Nazarene will have “Trunk or Treat.” Just a few blocks west, Monterey church of Christ will have also have a “Trunk or Treat.”


October 31st: Cookeville West Side Trick or Treat – Cookeville, TN

The City of Cookeville’s Department of Leisure Services, in conjunction with the West Side Business Association, is re-instating the West Side Trick or Treat event that was an autumn family staple in Cookeville for many years. This year’s trick or treat will be from 5:30-7:30 on Halloween evening, Tuesday, October 31, and will take place on Broad Street from Regions Bank to the Depot, with non-profits at trick-or-treat booths on the Depot grounds.


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