It’s fall! Bring on the hay rides, festivals, and barn sales! New to the area? Wondering what’s going on in the area? We’re here to give you the rundown. Check out these September events in Cookeville and the Upper Cumberland!

September Events in Cookeville and the Upper Cumberland

White County Fair

August 31st – September 8th · Sparta, Tennessee

Tractor pull, cornhole tournament, 4-wheeler races…don’t miss it! Check out the White County Fair!

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Cookeville Blues Jam

September 5th · Red Silo Brewing Company · Cookeville, Tennessee

Love blues? Calling all Blues fans and regular Blues Jammers! This event is the only open mic night in the Upper Cumberland area dedicated to celebrating and preserving the Blues. Bring your favorite I IV V Blues songs and let’s jam!

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Fall FunFest

September 7th – 8th · Cookeville, Tennessee

An annual tradition in Cookeville! This free event is full of food, games, music and craft vendors. You don’t want to miss it! Bring the kids!

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Wine, Art & Notes

September 8th · Highland Manor Winery · Jamestown, Tennessee

A festival of Wine, Art & Notes at Tennessee’s Oldest Winery, Highland Manor on Hwy 127 in Jamestown, TN. Alright, is this not the perfect date night idea? An afternoon of tasting delicious wines from 10 Tennessee wineries, regional artist & craft demonstrations, winery tours, food trucks & live music.


Saturday, Sept. 8, 2018 11 am – 5 pm.

*21+ to Taste, Bring ID to Check-in. Pre-sale tickets are $15 & $20 at Gate. 

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3rd Annual LickSkillet Barn Sale

September 14 – 15th · Livingston, Tennessee

Come out for a great day of shopping vintage, homemade goods, face painting, pumpkin painting, wagon rides, clothing, music, food, & fun! This is a great way to kick off the fall season!

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Sweet Onidas Barn Sale

September 21 – 22nd · Bloomington Springs, Tennessee

Y’all come out and bring the family! They have a little something for everyone. Shop with 30+ Artisans, jam out to live music, and eat great food! Feature: Farm House Decor, Jewerly, Antiques, One-of-a-Kind Handmade Items, Boutique Clothing, Re-purposed Treasures and more!

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Cork & Pork Festical

September 22nd · DelMonaco Winery & Vineyards · Baxter, Tennessee

What could be better than Wine, Music & “Finger Licking Good” Barbecue? The Cork & Pork Festival is a celebration of America’s biggest pastime showcasing Cookeville’s best BBQ cooking, fine wine, live music, and craft vendors from across the state. Cookeville’s top BBQ restaurants and local teams will serve up their specialties while competing for the People’s Choice Award traveling trophy and of course bragging rights!

Other activities include:
– Hayrides through the Vineyards
– Scavenger Hunt
– Wine themed games

Featured Live Music:
– 12:00 – 3:00PM Rusty Rooster is a local band based out of Monterey, TN. The band plays a number of “get ya dancin” original songs along with a wide mix of pure good old rock and roll.
– 4:00 – 7:00PM Soulfissh is a local 70’s, 80’s and 90’s rock band, ready to rock the house.

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2nd Year Anniversary Block Party

September 22nd · Red Silo Brewing Company · Cookeville, Tennessee

Cheers! Red Silo Brewing Company, a local favorite! Kick it at the brewery and join in as they celebrate their 2nd anniversary! Enjoy Food, Family, Friends, and Fun. All ages are welcome and free admission so bring everyone you know! Mark your calendars!

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2nd Annual Market Place

September 22nd · True West Campground & Stables · Jamestown, Tennessee

Love handcrafted items and gifts or just looking for something cool? Check it out!

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EAT Cookeville

September 24th 5:00 – 7:00PM · Cookeville, Tennessee

Curious how to judge cooking competitions like the World Food Championships (WFC)!? This is YOUR chance to become a Gold Card-carrying expert as an EAT Certified Food Champ Judge! This kitchen classroom experience is hosted by a certified Food Sport professional who takes you through our proprietary EAT Methodology so will be eligible to judge at any WFC event. Upon completion of the class, you will join our growing community of WFC Judges and receive a certified Food Champ Judge GOLD CARD to prove it!

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Fall Market

September 28th – 30th · Northfield Vineyards · Sparta, Tennessee

What’s better than hanging out at a cool vineyard on a fall day? Their annual fall market will feature over 50 vendors with food and music! Free admission and free parking!

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2018 Cookeville Whiskey Fest

September 28th · Happy Hour Wine & Liquor · Cookeville, Tennessee

Featuring over 100 different types of whiskeys and scotches! Local Cookeville craft beer and several wine options for the non-whiskey drinkers attending. Catered food from local restaurants and live music make for a great evening! 100% of proceeds go to charity!

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Whiskey Barrel Chandelier Barn Sale & Mum Festival

September 28 – 29th · Clydesdale Farms · Rickman, Tennessee

With a name like that, how can you not go! This festival includes Live music, Unique Shopping, Delicious food, and Artisan demonstrations.

Friday, September 28th · 4:00 – 9:00PM
Saturday 9/29 10:00AM – 6PM
All proceeds go to Rising Above Ministries

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Vintage Market Barn Sale

September 28 – 30th · Clarkrange, Tennessee

Have you ever been to barn sale? If not, you need to! It’s sorta a big thing in the south! See the latest designs from southern creators and makers! This event includes a weekend of mobile boutiques, arts & crafts, live music & more!


Friday, Sept 28 · 5:00 – 8:00PM
Saturday, Sept 29 · 10:00am – 8:00PM
Sunday, Sept 30 · 10:00am – 4:00PM

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Hosting an event? Want to get the word out about a local event? Let us know! Comment below and we will add the event to the list! 

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