Annual Events and Festivals

Art & Wine Festival

Date of Event: 
Friday, Nov 8, 2019 from 11:00 to 6:00
Saturday, Nov 9, 2019 from 9:30 to 4:00

This Friday-Saturday artist marketplace in November each year is Winnsboro’s cultural highlight event of the year. The artists are selected through a jury process so only the finest variety of artists will be in attendance.

Elm, Market and Franklin Streets are closed to traffic and lined with white tents housing a variety of art that ranges from traditional to abstract, painting to pottery, glass to silk.

More Information

Autumn Trails

Date of Event:  September 28 through November 2, 2019

For more than 60 years Autumn Trails has been an annual event in Winnsboro. It is the longest annual event in Winnsboro’s history. The celebration lasts throughout the month of October.

Every weekend is filled with events from Arts & Crafts, cook-offs, barrel racing, trail rides, livestock show and more.  New this year will be a Bowery Street dance.

More Information

Starry Starry Night

Date of Event: March 7, 2020 from 6:00 to 9:00 pm

This event is the Winnsboro Center for the Arts annual fundraiser.  The venue includes  original art from both amateur and professional artists. 

Mark your calendar for March 7, 2020.  Event starts at 6 pm with appetizers and a Silent Auction.  The evening continues with dinner and live auction at 7 pm. 

A live auction includes donated services and items from the East Texas area all the way to Dallas. 

More information

Starry Starry Night 2019 Fundraiser

Winnsboro Rodeo

4th Annual Open 5D – October 12, 2019 from 4:00 to 10 pm
Winnsboro Rodea Arena – 937 Wheeler Drive, Winnsboro

Exhibitions will be from 3-6:15 pm first come first serve with the actual race starting at 7:00pm. There will be a one time office charge of $10 and $30 entry fee. There is $500 guaranteed added money up to 100 entries and $1000 added at 101. It will be 80% payback with 100% added money. Text pre-entries will be on October 1st from 4-10pm to 903-629-5272.

Winnsboro Rodeo

First Annual Mule Rodeo – October 19, 2019 from 6:00 to 10 pm
Winnsboro Rodea Arena – 937 Wheeler Drive, Winnsboro

1st Annual Mule Rodeo will be held trail ride weekend. Events will be jackpot style and there will be a buckle for the All Around winner.

Events will be Monkey in a Tree, Hide Ride, Barrel Race and Musical Ring
Balloon Pop.

Fee: $5 per event w/ a $5 office fee per mule.

Antique Car Parade

A major attraction during the Autumn Trails month is the Antique Car and Parade and Model T Tour.  The parade historically has well over 150 cars participating.

The preservation of these antique cars and the variety makes it one of the largest antique car shows in the Southwest.

More Information

Casino Night Fundraiser

Date of Event:  February 8, 2020

The Friends of the Winnsboro Animal Shelter is a 501c3 non profit organization that supports the Winnsboro Animal Shelter.

Each year they hold a Casino Night to raise funds for this worthy cause.  Participants enjoy gaming, appetizers and a silent auction.

More Information

Farmers' Market

Open April through October from 8:00 to noon on Market St.

The Winnsboro Farmers’ Market brings producers of locally grown food, hand made, and home baked products together with discerning shoppers, to enhance the local economy and foster community relationships.

Locally grown produce and agricultural items are sold.  The market was the winner of “The Best Produce for 2018” in the Upper East Side of Texas.

More Information

Wellapalooza

Date of Event:  September 7, 2019 from 8 am to noon.

Wellapalooza is a collaboration of the Winnsboro Wellness Coalition & the Winnsboro Farmers’ Market.  The event is used to highlight the vast array of wellness, nutrition, and fitness opportunities to be found in our little town.  Enjoy live cooking demos, which utilize fresh market products, to create healthy & delicious meals.  Fitness sessions are also scheduled throughout the day.  Relax with a calming stretch routine, or get your heart pumping with local Zumba & Bootcamp instructors.  Feeling really adventurous?  Goat yoga may be the thing for you!  Wellapalooza is fun for the whole family!

The Market is open from April through October every Saturday from 8:00 am to Noon. Locally grown produce and agricultural items are sold.

Classic Car Cruise-In

Date of Event:  August 31, 2019 at the historic train depot in Winnsboro.

This annual event is popular with both the young and old.  All classic cars, trucks and motorcyles are welcome.  Music will be provided by the C.

Registration: 7:00 to 10:30 am
Judging: 11:00 am to 2 pm
Awards: 2:00 pm

For more information visit the Winnsboro Chamber of Commerce at 100 E. Broadway or call them at 903-342-3666.

Cruise into Winnsboro on Labor Day weekend and enjoy classic cars, music, shopping and food!

Close Menu