Best events in
Winnsboro

With a lively weekend rhythm centered on its historic downtown, there are many community-focused events and things to do in Winnsboro, TX. The designated Cultural Arts District provides a backdrop for concerts, gallery exhibits, and theatre productions. Annual festivals celebrate everything from local art and wine to cowboy poetry, adding to the town's distinct character.

The walkable Bowery district in downtown Winnsboro serves as a hub for evening entertainment, with dining spots and performance venues like The Bowery Stage.
Find a variety of live music, from folk and blues to cowboy tunes, at intimate venues within the Winnsboro Center for the Arts.
Celebrate local culture at annual happenings like the Autumn Trails festival or the juried Art & Wine Festival.

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Events near Winnsboro

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Darrell Scott on the Bowery Stage

Sat, Oct 10 • 7:30 PM

Winnsboro Center for the Arts

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Winnsboro Live! Brian Chance and Jason Waldon & the Alibis

Sat, Oct 10 • 7:30 PM

Jack Cross Pavillion

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Love Never Ends Trail Run

Sat, Oct 17 • 6:00 AM

Bell Ranch

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Leading Through Mergers and Acquisitions

Wed, Oct 21 • 5:30 PM

1000 Country Club Dr

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Prowl-O-Ween 2026

Sat, Oct 24 • 10:00 AM

Tiger Creek Animal Sanctuary

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Dolly Parton Tribute Show at the Historic Select Theater

Sat, Nov 7 • 7:00 PM

The Historic Select Theater 114 North Johnson Street, Mineola, Texas 75773

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PRESERVING TEXAS GRASSLANDS: Land Stewardship & Conservation Easements

Fri, Nov 13 • 9:00 AM

Ebel Grassland Ranch

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Friendsgiving Flights & Bites Good Friends. Good Wine. Grateful Hearts.

Sat, Nov 14 • 5:00 PM

Rowdy Creek Ranch

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Darrell Scott on the Bowery Stage

Sat, Oct 10 • 7:30 PM

Winnsboro Center for the Arts

Check ticket price on event

Winnsboro Live! Brian Chance and Jason Waldon & the Alibis

Sat, Oct 10 • 7:30 PM

Jack Cross Pavillion

Check ticket price on event

Love Never Ends Trail Run

Sat, Oct 17 • 6:00 AM

Bell Ranch

Check ticket price on event

Leading Through Mergers and Acquisitions

Wed, Oct 21 • 5:30 PM

1000 Country Club Dr

Check ticket price on event

Prowl-O-Ween 2026

Sat, Oct 24 • 10:00 AM

Tiger Creek Animal Sanctuary

Check ticket price on event

Dolly Parton Tribute Show at the Historic Select Theater

Sat, Nov 7 • 7:00 PM

The Historic Select Theater 114 North Johnson Street, Mineola, Texas 75773

Check ticket price on event

PRESERVING TEXAS GRASSLANDS: Land Stewardship & Conservation Easements

Fri, Nov 13 • 9:00 AM

Ebel Grassland Ranch

Check ticket price on event

Friendsgiving Flights & Bites Good Friends. Good Wine. Grateful Hearts.

Sat, Nov 14 • 5:00 PM

Rowdy Creek Ranch

Check ticket price on event

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Nearby cities

Tyler

44 miles away

Longview

44 miles away

Greenville

49 miles away

Mineola

24 miles away

Mount Pleasant

24 miles away

Gilmer

24 miles away

Lindale

31 miles away

Canton

43 miles away

Liberty City

41 miles away

Gladewater

35 miles away

Winona

33 miles away

Emory

28 miles away

Sulphur Springs

22 miles away

Como

13 miles away

Van

36 miles away

Wills Point

45 miles away

White Oak

39 miles away

Tyler

44 miles away

Longview

44 miles away

Greenville

49 miles away

Mineola

24 miles away

Mount Pleasant

24 miles away

Gilmer

24 miles away

Lindale

31 miles away

Canton

43 miles away

Liberty City

41 miles away

Gladewater

35 miles away

Winona

33 miles away

Emory

28 miles away

Sulphur Springs

22 miles away

Como

13 miles away

Van

36 miles away

Wills Point

45 miles away

White Oak

39 miles away

Online Events

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wednesday • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 6:00 PM EDT

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wednesday • 7:30 PM GMT+1

Check ticket price on event

AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 6:00 PM EDT

Check ticket price on event

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Winnsboro

What are some popular family-friendly events in Winnsboro?

The annual Autumn Trails festival is a great family-friendly event. This month-long celebration includes trail rides, arts and crafts, and an antique car parade. The seasonal Winnsboro Farmers' Market on Saturday mornings also offers a welcoming atmosphere for all ages.

Where can I find live music events in Winnsboro?

The Bowery Stage is the top spot for intimate live music shows. Located within the Winnsboro Center for the Arts, it hosts singer-songwriters, folk, and blues acts. The annual Cowboy Music and Poetry Gathering is another key music event celebrating regional heritage.

Are there free things to do in downtown Winnsboro?

Exploring the historic downtown Cultural Arts District is a wonderful free activity. Visitors can browse art galleries and boutiques along Market Street. Many annual festivals also feature free-to-attend components like parades and street markets.

How can I experience the local art scene?

Visit the Winnsboro Center for the Arts in the downtown Cultural Arts District. This central hub hosts art exhibits, theatre productions, and classes. For a major art event, look for the annual Art & Wine Festival, a juried market featuring regional artists.

What kind of food and drink events happen in Winnsboro?

The annual Art & Wine Festival highlights regional food and drink culture. This event brings Texas wineries and craft breweries to the downtown area. For local produce and goods, the seasonal Winnsboro Farmers' Market is a popular community gathering.

What is a good spot for a date night in Winnsboro?

The Bowery Stage offers an intimate setting perfect for a date night. This listening room hosts folk, jazz, and blues performers in a cozy atmosphere. Before a show, enjoy dinner at one of the nearby restaurants in the walkable Bowery district.

Does Winnsboro have much nightlife?

Winnsboro's nightlife centers on its walkable downtown and Bowery district. The scene is more about enjoying a concert or a late dinner than bustling clubs. The Bowery Stage within the Winnsboro Center for the Arts is a key venue for evening entertainment.

What's the best way to explore The Bowery district?

The best way to explore The Bowery is on foot. This compact, historic area is part of the downtown Cultural Arts District and features boutiques and galleries. It is also home to the Winnsboro Center for the Arts, a central point for community events.

Events near Winnsboro

Darrell Scott on the Bowery Stage

Winnsboro Live! Brian Chance and Jason Waldon & the Alibis

Love Never Ends Trail Run

Leading Through Mergers and Acquisitions

Prowl-O-Ween 2026

Dolly Parton Tribute Show at the Historic Select Theater

PRESERVING TEXAS GRASSLANDS: Land Stewardship & Conservation Easements

Friendsgiving Flights & Bites Good Friends. Good Wine. Grateful Hearts.

Darrell Scott on the Bowery Stage

Winnsboro Live! Brian Chance and Jason Waldon & the Alibis

Love Never Ends Trail Run

Leading Through Mergers and Acquisitions

Prowl-O-Ween 2026

Dolly Parton Tribute Show at the Historic Select Theater

PRESERVING TEXAS GRASSLANDS: Land Stewardship & Conservation Easements

Friendsgiving Flights & Bites Good Friends. Good Wine. Grateful Hearts.

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Nearby cities

Tyler

Longview

Greenville

Mineola

Mount Pleasant

Gilmer

Lindale

Canton

Liberty City

Gladewater

Winona

Emory

Sulphur Springs

Como

Van

Wills Point

White Oak

Tyler

Longview

Greenville

Mineola

Mount Pleasant

Gilmer

Lindale

Canton

Liberty City

Gladewater

Winona

Emory

Sulphur Springs

Como

Van

Wills Point

White Oak

Online Events

A Norman stitch-up? The story behind the Bayeux Tapestry

AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

HBR Press Webinar: Resilient Optimism

HBR Book Webinar: Resilient Optimism

(ONLINE) Women on the Move with Ann Patchett

No Title, No Permission, No Problem: Harnessing the Power of Influence

Lean Global Connection 2026

Washington Crossing the Delaware / The Crossing - Film History Livestream

A Norman stitch-up? The story behind the Bayeux Tapestry

AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

HBR Press Webinar: Resilient Optimism

HBR Book Webinar: Resilient Optimism

(ONLINE) Women on the Move with Ann Patchett

No Title, No Permission, No Problem: Harnessing the Power of Influence

Lean Global Connection 2026

Washington Crossing the Delaware / The Crossing - Film History Livestream

Things to do around Winnsboro