Downtown Tupelo

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Downtown Tupelo Downtown Tupelo Main Street Association’s mission is to sustain and enhance the Downtown experience.

Fall Into Tupelo 2026 keeps rolling on with Ale Trail presented by FNB Tupelo Bank on Friday, October 30! Tickets are ON...
10/19/2026

Fall Into Tupelo 2026 keeps rolling on with Ale Trail presented by FNB Tupelo Bank on Friday, October 30! Tickets are ON SALE NOW! 🍻
https://www.eventbrite.com/e/2026-downtown-tupelo-ale-trail-presented-by-fnb-tupelo-tickets-2001894296731?aff=oddtdtcreator&keep_tld=true

Ale Trail Stops:
Citizens Style
Guaranty Bank
Reed's
Liz Beavers Team - Jason Warren & Associates Inc
BankFirst Financial Services
GumTree Museum of Art
BlairHaus Interiors
Bolt Tupelo
Community Bank
Fleet Feet Tupelo

Circle back to FNB Tupelo Bank Courtyard for one last tasting and an Afterparty featuring bites from Fairpark Grill and music from Joshua J McCloud.

All b**r provided by Mitchell Distributing.

A well-seasoned Friday night in Downtown Tupelo!!! 🌶️🔥 The 27th Annual Tupelo Chili Festival raised the bar and brought ...
10/17/2026

A well-seasoned Friday night in Downtown Tupelo!!! 🌶️🔥 The 27th Annual Tupelo Chili Festival raised the bar and brought the heat. Until next year!!! 💚💛💙

And don’t forget Fall Into Tupelo 2026 keeps rolling with Ale Trail presented by FNB Bank on October 30. Tickets on sale now: https://www.tupelomainstreet.com/aletrail

10/17/2026

The temps were chilly, but the chili was 🔥 HOT! What a great night at the 27th Annual Tupelo Chili Festival at Fairpark!

A huge THANK YOU to all of our participating teams, sponsors, volunteers, and everyone who came out to enjoy the fun, sample some chili, and support this awesome community tradition. ❤️

And now, let’s give a round of applause to this year’s winners! 🏆🎉

🌟 SPECIAL AWARDS
🏅 Best Presentation: Tupelo Development Services
🔥 Spiciest Chili: Byrd Insurance Agency
🍲 Most Original Recipe: Knights of Saint Andrew
🥇 Best of Team Tupelo (Best City Department): Tupelo Fire Department

❤️ People’s Choice Award: Tupelo Fire Department

🌶️ BEST CHILI OVERALL
🥉 3rd Place: Rollin’ Bandits
🥈 2nd Place: Guaranty Bank
🥇 1st Place: Byrd Insurance Agency

Until next year, stay warm and keep it spicy, Tupelo! 💚💛💙

🌶️🔥 TONIGHT, TUPELO!!! IT’S CHILI TIME!!!🔥🌶️Grab your friends, bring your appetite, and get ready for a night full of de...
10/16/2026

🌶️🔥 TONIGHT, TUPELO!!! IT’S CHILI TIME!!!🔥🌶️

Grab your friends, bring your appetite, and get ready for a night full of delicious chili, live music, and Fall Into Tupelo 2026! 🍁🎶

🌶️ HERE’S WHAT YOU NEED TO KNOW:

🥣 $10 CHILI TASTING – Tickets are available ON SITE ONLY! Sample all the chilis and cast your vote for the People’s Choice Award! 🏆

💵 CASH IS KING! We do accept credit cards, but cash is recommended for faster checkout!

🍻 READY FOR A DRINK: Don’t forget your ID! You MUST show your ID and get a wristband to purchase alcohol.

TONIGHT's SCHEDULE:
🌶️ 5:30 PM – Chili tasting begins!
🎸 6:30 PM – Reed Brake Music hits the stage!
🏆 8:30 PM – Judges’ Awards announced!

WHO’S READY?! 🙋‍♀️🙋‍♂️🔥

The 27th Annual Tupelo Chili Festival is taking over Fairpark in Downtown Tupelo this Friday, October 16!🌶️ $10 tasting ...
10/13/2026

The 27th Annual Tupelo Chili Festival is taking over Fairpark in Downtown Tupelo this Friday, October 16!

🌶️ $10 tasting tickets = taste the chilis + vote for your favorite!

🏆SOUND OFF IN THE COMMENTS! 👇 Which team is taking home the win this year? Let’s hear it!

📅 Friday, October 16
📍 Fairpark | Downtown Tupelo
⏰ 5:30 PM — Tasting begins
🎶 6:30 PM — Live music with Reed Brake Music

Fall Into Tupelo 2026

10/12/2026

Don't miss our friends at Boys & Girls Clubs of North Mississippi's annual BURGER BASH this Thursday at The Depot!!! While you're there pickup a Fall Into Tupelo 2026 Family Fun Day pumpkin courtesy of the Jarrell Group, LLC. 🎃💚💛💙

TUPELO CHILI FESTIVAL IS THIS FRIDAY! 🔥🌶️📍 Fairpark | Downtown Tupelo📅 Friday, October 16 | 5:30 PM🎟️ Just $10 to sample...
10/12/2026

TUPELO CHILI FESTIVAL IS THIS FRIDAY! 🔥🌶️

📍 Fairpark | Downtown Tupelo
📅 Friday, October 16 | 5:30 PM
🎟️ Just $10 to sample the chilis!

🌶️ Delicious chili & People’s Choice voting
🚚 Food trucks on site
🍻 Beverage tent sponsored by Mitchell Distributing & Coca-Cola of Tupelo
🎸 Live music by Reed Brake Music

Bring your friends and appetite for a night of great food, drinks, and music! ❤️🔥

Fall Into Tupelo 2026

🌧️ Mother Nature has other plans for us this Saturday! Unfortunately, Family Fun Day at The Depot, scheduled for October...
10/09/2026

🌧️ Mother Nature has other plans for us this Saturday! Unfortunately, Family Fun Day at The Depot, scheduled for October 10, has been postponed due to the forecasted storm and strong winds.

While we’re sad to press pause on the fun, we’re hopeful we’ll have another opportunity to bring everyone together in the future! 💚💛💙

A HUGE thank you to our amazing nonprofit partners, generous sponsors, and everyone who planned to participate. Your support means so much to us, and we’re grateful to have you as part of our community! Keep watching our social media channels for updates as we hope to revisit this event in the future.

But the fun doesn’t stop here! 🌶️ Join us NEXT FRIDAY, October 16, for Tupelo Chili Fest at Fairpark as we keep the Fall Into Tupelo 2026 activities rolling! 🍂

City of Tupelo - Mayor's Office
My Tupelo
Team Tupelo
Tupelo Parks and Recreation
Tupelo360
WTVA 9 News
Daily Journal
WCBI News

🌴 Weekend plans? Add a little tiki to the itinerary. 🍹 Hachi Machi Tupelo is waiting at Broadway & Main. ✨
10/08/2026

🌴 Weekend plans? Add a little tiki to the itinerary. 🍹 Hachi Machi Tupelo is waiting at Broadway & Main. ✨

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108 S Broadway Street
Tupelo, MS
38804

Opening Hours

Monday 8am - 5pm
Tuesday 8am - 5pm
Wednesday 8am - 5pm
Thursday 8am - 5pm
Friday 8am - 5pm

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