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Country concerts this month in Winter Garden, FL
Find tickets to concerts, tour dates and live music near Winter Garden, FL
Winter Garden, FL
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Layla Brisbois
Sun, Oct 18 • 3:30 PM
Crooked Can Brewing Company
Calling Crystal
Sun, Oct 18 • 6:00 PM
PRIVATE EVENT
PSALM 101
Sun, Oct 18 • 6:00 PM
Park Ave Church of God
Mylie Taylor
Mon, Oct 19 • 7:00 PM
The Social
Drag the River
Wed, Oct 21 • 12:00 PM
ORLANDO Drag The River Band
Layla Brisbois
Wed, Oct 21 • 6:00 PM
Crooked Can Brewery
Jordan Mohr
Wed, Oct 21 • 6:00 PM
Ole Red Orlando- DUO
Layla Brisbois
Thu, Oct 22 • 12:00 PM
Ednas' on the Green
Wyatt Flores
Thu, Oct 22 • 7:00 PM
Kia Center
Teddy Swims
Thu, Oct 22 • 7:00 PM
Kia Center
Ian McConnell
Thu, Oct 22 • 8:30 PM
Will's Pub
EXIT LEFT
Fri, Oct 23 • 1:00 PM
Exit Left Live Music Friday at Amerikanos – Lady Lake
Never 2 Late Duo
Fri, Oct 23 • 6:00 PM
N2L at Bree's Riverside Restaurant
Alafia Swampers
Fri, Oct 23 • 8:00 PM
Alafia Swampers — Duke’s Brewhouse · Lakeland (Full band)
Nathan Allen Music
Fri, Oct 23 • 8:00 PM
The Brass Tap
Steve Angel
Sat, Oct 24 • 1:00 PM
Oktoberfest featuring The Steve & Monika Euromusik Experience
The Tom Haney Band
Sat, Oct 24 • 1:00 PM
MiniMesaris 2026
Melissa Lee
Sat, Oct 24 • 7:00 PM
The Chop Shop
NoFilter
Sat, Oct 24 • 7:30 PM
Boxi Park Lake Nona
PSALM 101
Sun, Oct 25 • 10:00 AM
First Baptist Church of Webster, FL
Calling Crystal
Sun, Oct 25 • 10:30 AM
Hard Rock Hotel - The Kitchen
Nathan Allen Music
Sun, Oct 25 • 2:00 PM
Tin Roof Orlando
Mitch Rossell
Sun, Oct 25 • 5:00 PM
Mitch Rossell @ Judson's Live
Calling Crystal
Sun, Oct 25 • 6:00 PM
PRIVATE EVENT
Mitch Rossell
Sun, Oct 25 • 7:30 PM
Mitch Rossell @ Judson's Live
Lauren Alaina
Mon, Oct 26 • 5:30 PM
EPCOT International Food & Wine Festival - Eat to the Beat Concert Series 2026
Calling Crystal
Tue, Oct 27 • 2:00 PM
Dockside Margaritas at Disney Springs
Lauren Alaina
Tue, Oct 27 • 5:30 PM
EPCOT International Food & Wine Festival - Eat to the Beat Concert Series 2026
Layla Brisbois
Wed, Oct 28 • 6:00 PM
Crooked Can Brewery
Rachel and George
Wed, Oct 28 • 7:00 PM
Lil Indies
The Tom Haney Band
Wed, Oct 28 • 7:00 PM
Love is Like a Butterfly
Hotel California A Salute to the Eagles
Wed, Oct 28 • 7:00 PM
Orange Blossom Opry
Rachel and George
Wed, Oct 28 • 9:00 PM
Will's Pub
Layla Brisbois
Thu, Oct 29 • 12:00 PM
Ednas' on the Green
Jordan Mohr
Thu, Oct 29 • 6:30 PM
Mohr Southern Sessions - Writer's Round
Calling Crystal
Thu, Oct 29 • 7:00 PM
PRIVATE EVENT
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