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5 Fall Things To Do In Madisonville

Updated: Oct 2, 2024

Have a feast at Food Truck Mondays

On the first Monday of each month, food trucks come to downtown Madisonville for an evening food festival. Food Truck Mondays start in April and end in October so you can visit in the Spring and Summer but we recommend visiting in the Fall (September and October) when the weather becomes cooler. Summers here can get really hot and humid; no one wants to wait in line outside in that weather. The trucks can be found at Memorial Park in downtown Madisonville along with live musical performances and a market with local vendors. Check the Facebook page to stay up to date on who will be at the festival each month.

A group of food trucks at a parking lot with festive lighting and picnic tables.
Food Truck Mondays

Haunt happy at Halloween in the City

Appalachia has a reputation of being a spooky place with many folk tales of ghosts and cryptids. Don't be a foolish mortal wandering into the woods looking for a fright. Instead, you'll want to walk (in a slow, creepy manner if you really want) into downtown Madisonville for Halloween in the City. Kids and the young-at-heart can dress up and go trick-or-treating. Kids aged 4-12 can take part in the costume contest. This is a safe, family-oriented event with local businesses and organizations handing out treats.

Treak-or-treaters at a candy stand at Halloween in the City
Halloween in the City

Get scared straight at the Haunted Jail

Visitors looking for a scare need to go to jail. We aren't joking. The old Monroe County Jail in downtown Madisonville is rumored to be haunted and these supposed spirits become corporeal as the jail is opened to the public as a haunted house. This attraction is hosted by Haunted Horrors and features scare actors lurking in the old cells, ready to frighten you. Doors to the Haunted Jail creak open at 07 PM on select dates and tickets costs $15. A food truck will be parked outside.

Poster for the Haunted Jail featuring a scare actor in a prison uniform
Cell Block 13 Haunted Jail

Sample local cuisine at Taste of Monroe

Monroe County has so many amazing places to eat and this one-day food festival celebrates our rich collection of restaurants. Visitors can sample dishes from eateries like Donna's Cafe, Iron Works Grille, and Señor Lopez Mexican Grill. The festival is hosted by the Monroe County Chamber of Commerce and coincides with the Chamber Member Business Expo which showcases local businesses. This is not just an event for adults, it also includes activities for kids including games and face painting. Taste of Monroe is held at Memorial Park in downtown Madisonville.

Two little girls having fun at Taste of Monroe
Two little girls having fun at Taste of Monroe

Grab some wild grapes at Tsali Notch Vineyard U-Pick

Also known as UPIC, this is a two-month event at Tsali Notch Vineyard in which visitors can pick their own muscadines, an indigenous variety of grape. The event starts Labor Day weekend and ends in late October with the peak ripeness being in late September and early October. UPIC can be done any day the vineyard is open in this period. The process starts by getting a branded one-gallon bucket (which costs $16) and you have around 10 minutes to fill the bucket with all the muscadines you can find in one spot. The bucket holds 6-8 pounds. If you really want more, you can pay $10 for a refill. For more information, text UPIC to 423 417 9463.

A vine of muscadines.
Tsali Notch Vineyard U-Pick

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