Sip, Stroll, and Stay in Style: The 2025 Winnsboro Art & Wine Festival Returns November 7–8

Each November, Winnsboro’s charming downtown transforms into an artist’s dream and wine lover’s paradise, and this year’s Winnsboro Art & Wine Festival promises to be the best one yet.

Mark your calendars for Friday, November 7, from 1–7 p.m. (with wineries open until 8 p.m.) and Saturday, November 8, from 10 a.m.–5 p.m., when Main Street fills with color, creativity, and the sweet sound of live music.

This juried festival draws talented artists from across the country, each bringing original works ranging from fine art and jewelry to sculpture, photography, and more. But art isn’t the only thing on display. Texas wineries like :

Landon Winery,

Cicada Ridge Vineyard,

Maydelle Wines,

Wall Street Winery,

Beyond the Vine Cellars,

Los Pinos Ranch Vineyards,

Cypress Creek Southern Ales,

Phinesse’ Farms, and

Un Sueno Vineyard 

will be offering tastings and bottles for sale throughout the weekend.

Add to that an irresistible lineup of specialty foods including:

Mac Daddy’s mac & cheese,

D&R Gourmet Blends olive oils,

East Texas Kettle Corn,

Grazed & Co charcuterie boxes,

La Dona Mexican food,

Winnsburger smashburgers and tots,

and Lonestar Mastiffs Farms jams, sauces, and seasonings

And you’ve got yourself a festival that’s a true feast for the senses.

Music to Set the Mood at the Art & Wine Festival

Live music fills the air both days with performances from talented local favorites:🎶 Friday, November 7 :

David Lindley kicks things off with easy-going classics that pair perfectly with a glass of Texas wine.🎶

Saturday, November 8 :

Enjoy soulful sets from Meredith Crawford & Chris Rasco, Kevin Tinney & Chase Glover, and Eve’s Road, whose dreamy alternative rock soundscapes will close out the event in style.

A Celebration of Winnsboro’s Creative Heart

Winnsboro takes pride in being one of the first seven officially designated Cultural Arts Districts in Texas , a recognition we’ve proudly held since 2009. At the center of it all is the Winnsboro Center for the Arts, whose mission is to nurture creativity and enrich our community through music, art, and cultural events like this one.

This festival is made possible by the generous support of sponsors, including:

The Winnsboro Economic Development Corporation,

Wood County Economic Development Commission,

County Line Magazine,

First National Bank of Winnsboro,

and others, along with grants from the National Endowment for the Arts and the Texas Commission on the Arts.

Stay in the Heart of It All at Oaklea Mansion

If you’re visiting for the festival, why not make a weekend of it? Oaklea Mansion, just steps away from downtown Winnsboro, offers a luxurious retreat filled with history, Southern charm, and a front-row seat to the festivities.

Enjoy a peaceful morning on the veranda, stroll downtown for a glass of wine and live music, and return to the mansion for a restful evening surrounded by elegance. Whether you’re an artist, collector, or simply a lover of good wine and good company, Oaklea Mansion is the perfect place to stay for the 2025 Winnsboro Art & Wine Festival.

📍 Book your stay now — rooms fill quickly during festival weekend!👉 Reserve your room at Oaklea Mansion