THIRD MONDAYS - MONDAY NIGHT LIVE - APR-NOV
Market Street comes alive with restaurant extended-premises, live entertainment, market vendors, arts & crafts, wineries, and local non-profit groups! It is one BIG block party! This event takes place from 5pm to 8pm on the third Monday of the selected months of March, April, May, June, September, October, & November. The live entertainment offers a variety of genres, with performances from local talent, and it is not unusual to see Nationally known singer/songwriters taking the stage as well! Winnsboro’s Main Street Program takes the lead on Monday Night Live, which is free to the public, and one can truly feel a sense of community as folks from Winnsboro and the surrounding area converge for a wonderful social event.
ART AND WINE FESTIVAL - NOV
Join us for the Premier Art event of Winnsboro. Historic Winnsboro is transformed into an art and wine lover's Mecca. Downtown streets are closed to traffic and everyone is welcome to this free festival. Art ranges from traditional to abstract, painting to pottery, glass to silk - a feast for the eyes.
AUTUMN TRAILS - OCT
Autumn Trails is a whole month of activity. Some of the events are:
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Arts & Crafts on Market Street
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The Grand Parade
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Antique Car Weekend
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Traders Day Swap Meet
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Trail Ride Weekend
CLASSIC CAR CRUISE IN - SEP
“Muscle-cars, antiques, and other classic cars descend upon Winnsboro on Friday, with many staying through Sunday for all the activity. The Chamber of Commerce hosts this well-attended event, which usually takes place over Labor Day Weekend.”
BONNIE & CLYDE IN WINNSBORO
The “Bonnie & Clyde’s Last Ride” Walking Tour takes place during the nationally recognized Historic Preservation Month of May, at the historic Depot, with reenactments on the streets of downtown. Winnsboro embraces its colorful heritage. By no means does the tour glamorize the lives of the notorious outlaws—Bonnie & Clyde—but it is a fact that they treated Winnsboro as one of their hide-outs from the law, and have become part of the town’s folklore.
