Winter Park, FL

Winter Park Country Tickets

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Trending Winter Park Events

Megan Woods
Megan Woods
May 16 • 7:00PM
Church of the Lakes
Leesburg, FL
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A man with a beard and sunglasses plays an acoustic guitar on stage.
Steve Earle
Jun 7 • 7:00PM
Mount Dora Live
Mount Dora, FL
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A male singer in a camouflage hat and torn black shirt performs on stage with red stage lights.
Hardy
Apr 25 • 7:00PM
Kia Center
Orlando, FL
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A man with a beard sings into a microphone, wearing a sparkly jacket and a black baseball cap.
Nate Smith - Country
Apr 9 • 7:30PM
House Of Blues - Orlando
Orlando, FL
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Man with undercut and ponytail wearing an orange shirt, facing away from the camera, with stage lights behind him.
Redferrin
May 24 • 7:00PM
House Of Blues - Orlando
Orlando, FL
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A person from behind wearing a camouflage shirt on a stage with a crowd in the background.
Whiskey Myers
May 29 • 6:00PM
Riverfront Park - Cocoa Village
Cocoa, FL
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A blonde woman in a sparkly blue dress plays a bedazzled acoustic guitar on stage.
Megan Moroney
Jul 16 • 7:00PM
Kia Center
Orlando, FL
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A singer with blond hair, wearing a t-shirt with a picture of a man, and jeans, performs on stage with red lighting.
Cooper Alan
May 31 • 8:00PM
The Plaza Live
Orlando, FL
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Lee Brice performs on stage, wearing a green hat and playing a guitar.
Lee Brice
Mar 20 • 6:00PM
Apopka Amphitheater
Apopka, FL
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Winter Park Country Schedule

2-23-25
Mar 20
Fri • 6:00 PM
Fri
Mar 20
6:00 PM
Lee Brice
Apopka Amphitheater
Apopka, FL
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2-23-25
Mar 20
Fri • 8:30 PM
Fri
Mar 20
8:30 PM
Josh Meloy
Tuffy's Music Box
Sanford, FL
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2-23-25
Mar 22
Sun • 7:00 PM
Sun
Mar 22
7:00 PM
Martin Sexton
Tuffy's Music Box
Sanford, FL
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2-23-25
Mar 25
Wed • 7:30 PM
Wed
Mar 25
7:30 PM
The Lovin' Spoonful
Ormond Beach Performing Arts
Ormond Beach, FL
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2-23-25
Mar 28
Sat • 2:30 PM
Sat
Mar 28
2:30 PM
Rhonda Vincent
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Mar 28
Sat • 7:00 PM
Sat
Mar 28
7:00 PM
Rhonda Vincent
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Mar 29
Sun • 2:30 PM
Sun
Mar 29
2:30 PM
Tracy Byrd
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Mar 29
Sun • 7:00 PM
Sun
Mar 29
7:00 PM
Tracy Byrd
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Mar 29
Sun • 8:00 PM
Sun
Mar 29
8:00 PM
Drake Milligan
Tuffy's Music Box
Sanford, FL
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2-23-25
Apr 6
Mon • 7:00 PM
Mon
Apr 6
7:00 PM
Billie Marten
The Social - FL
Orlando, FL
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2-23-25
Apr 9
Thu • 7:00 PM
Thu
Apr 9
7:00 PM
Classic Country
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Apr 9
Thu • 7:30 PM
Thu
Apr 9
7:30 PM
Nate Smith - Country
House Of Blues - Orlando
Orlando, FL
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2-23-25
Apr 10
Fri • 7:00 PM
Fri
Apr 10
7:00 PM
Crystal Gayle
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Apr 11
Sat • 1:30 PM
Sat
Apr 11
1:30 PM
Crystal Gayle
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Apr 14
Tue • 6:00 PM
Tue
Apr 14
6:00 PM
Cooper Alan
Lakeland Linder International Airport
Lakeland, FL
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2-23-25
Apr 16
Thu • 7:30 PM
Thu
Apr 16
7:30 PM
Sammy Kershaw
Dr. Phillips Center - Steinmetz Hall
Orlando, FL
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2-23-25
Apr 17
Fri • 7:00 PM
Fri
Apr 17
7:00 PM
Canaan Cox
Will's Pub
Orlando, FL
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2-23-25
Apr 24
Fri • 6:30 PM
Fri
Apr 24
6:30 PM
Maren Morris
House Of Blues - Orlando
Orlando, FL
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2-23-25
Apr 24
Fri • 9:00 PM
Fri
Apr 24
9:00 PM
Kolby Cooper
Tuffy's Music Box
Sanford, FL
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2-23-25
Apr 25
Sat • 7:00 PM
Sat
Apr 25
7:00 PM
Hardy
Kia Center
Orlando, FL
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2-23-25
Apr 25
Sat • 7:00 PM
Sat
Apr 25
7:00 PM
Russell Dickerson
Addition Financial Arena
Orlando, FL
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2-23-25
Apr 29
Wed • 7:00 PM
Wed
Apr 29
7:00 PM
Brenn!
The Social - FL
Orlando, FL
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2-23-25
May 1
Fri • 7:00 PM
Fri
May 1
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
May 1
Fri • 7:30 PM
Fri
May 1
7:30 PM
Marty Stuart and His Fabulous Superlatives
Mainstage Theatre at Reilly Arts Center - Ocala
Ocala, FL
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2-23-25
May 8
Fri • 7:00 PM
Fri
May 8
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
May 14
Thu • 7:00 PM
Thu
May 14
7:00 PM
Classic Country
Orange Blossom Opry
Weirsdale, FL
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2-23-25
May 15
Fri • 7:00 PM
Fri
May 15
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
May 16
Sat • 7:00 PM
Sat
May 16
7:00 PM
Megan Woods
Church of the Lakes
Leesburg, FL
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2-23-25
May 17
Sun • 7:00 PM
Sun
May 17
7:00 PM
Megan Woods
Reach City Church
Riverview, FL
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2-23-25
May 20
Wed • 7:00 PM
Wed
May 20
7:00 PM
Clare Bowen & Jonathan Jackson
Funny Bone Comedy Club - Orlando
Orlando, FL
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2-23-25
May 22
Fri • 7:00 PM
Fri
May 22
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
May 24
Sun • 7:00 PM
Sun
May 24
7:00 PM
Redferrin
House Of Blues - Orlando
Orlando, FL
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2-23-25
May 29
Fri • 6:00 PM
Fri
May 29
6:00 PM
Whiskey Myers
Riverfront Park - Cocoa Village
Cocoa, FL
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2-23-25
May 29
Fri • 7:00 PM
Fri
May 29
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
May 30
Sat • 7:00 PM
Sat
May 30
7:00 PM
Ian Munsick
Riverfront Park - Cocoa Village
Cocoa, FL
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2-23-25
May 30
Sat • 8:00 PM
Sat
May 30
8:00 PM
49 Winchester
The Plaza Live
Orlando, FL
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2-23-25
May 31
Sun • 8:00 PM
Sun
May 31
8:00 PM
Cooper Alan
The Plaza Live
Orlando, FL
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2-23-25
Jun 5
Fri • 7:00 PM
Fri
Jun 5
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Jun 7
Sun • 7:00 PM
Sun
Jun 7
7:00 PM
Steve Earle
Mount Dora Live
Mount Dora, FL
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2-23-25
Jun 11
Thu • 7:00 PM
Thu
Jun 11
7:00 PM
Classic Country
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Jun 12
Fri • 7:00 PM
Fri
Jun 12
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Jun 18
Thu • 7:30 PM
Thu
Jun 18
7:30 PM
Vince Gill
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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2-23-25
Jun 19
Fri • 7:00 PM
Fri
Jun 19
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
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2-23-25
Jun 26
Fri • 7:00 PM
Fri
Jun 26
7:00 PM
Bobby Randall and The OBO Band
Orange Blossom Opry
Weirsdale, FL
Get Tickets
2-23-25
Jul 10
Fri • 7:30 PM
Fri
Jul 10
7:30 PM
Jake Hoot
Mainstage Theatre at Reilly Arts Center - Ocala
Ocala, FL
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2-23-25
Jul 16
Thu • 7:00 PM
Thu
Jul 16
7:00 PM
Megan Moroney
Kia Center
Orlando, FL
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2-23-25
Sep 9
Wed • 8:00 PM
Wed
Sep 9
8:00 PM
Charley Crockett
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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Find the Best Country Concerts in Winter Park for 2026

Winter Park is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular country concerts so you can easily plan your next outing.

Top 2026 Summer Country Concerts in Winter Park

Summer is the perfect time for live events in Winter Park! Check out this list of the top country concerts happening from May through September.

Event Name Date Venue Lowest Price
Megan Woods May 16 Church of the Lakes $76
Megan Woods May 17 Reach City Church $90
Bobby Randall and The OBO Band May 22 Orange Blossom Opry $52
Redferrin May 24 House Of Blues - Orlando $58
Whiskey Myers May 29 Riverfront Park - Cocoa Village $75
Ian Munsick May 30 Riverfront Park - Cocoa Village $74
Cooper Alan May 31 The Plaza Live $75
Steve Earle Jun 7 Mount Dora Live $66
Vince Gill Jun 18 Dr. Phillips Center - Walt Disney Theater $78
Megan Moroney Jul 16 Kia Center $154

Top Venues in Winter Park, FL

an exterior picture of the kia center from across the street during sunset
Kia Center
Orlando, FL
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an exterior picture of the dr phillips center walt disney theater from across the street during sunset
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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an exterior promotional venue picture of dr phillips center steinmetz hall with a sunset sky
Dr. Phillips Center - Steinmetz Hall
Orlando, FL
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SanJoseCivic_SanJoseCA-Leonardo
House Of Blues - Orlando
Orlando, FL
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a realistic drone promo venue photograph of the daytona international speedway at sunset.
Daytona International Speedway
Daytona Beach, FL
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an interior promotional picture of the stage at orlando improv
Funny Bone Comedy Club - Orlando
Orlando, FL
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an exterior promotional venue picture of the plaza live with a sunny sky
The Plaza Live
Orlando, FL
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publix field at joker marchant stadium
Publix Field at Joker Marchant Stadium
Lakeland, FL
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a cinematic photograph of the cirque du soleil building at disney springs in orlando, florida, captured at sunset.
Cirque du Soleil - Disney Springs
Orlando, FL
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an exterior promotional venue picture of peabody auditorium with a sunset sky
Peabody Auditorium
Daytona Beach, FL
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All Venues Near Winter Park, FL