Winter Park, FL

Winter Park Country Tickets

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Trending Winter Park Events

A man in a striped shirt sings and plays a hollow-body electric guitar on stage.
The Red Clay Strays, The Revivalists & Haley Reinhart
Oct 14 • 6:30PM
Kia Center
Orlando, FL
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Clint Black plays acoustic guitar and harmonica on stage.
Clint Black
Sep 18 • 7:30PM
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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A man in a cowboy hat sings into a microphone while playing an acoustic guitar on stage.
Charley Crockett
Sep 9 • 8:00PM
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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little big town performing on stage at the ohio stadium in columbus, ohio.
Little Big Town
Sep 25 • 7:30PM
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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Yaelokre
Yaelokre
Nov 9 • 7:00PM
The Beacham
Orlando, FL
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A man wearing a baseball cap plays an acoustic guitar and sings into a microphone.
Dylan Gossett, Buffalo Traffic Jam & The Jack Wharff Band
Nov 21 • 6:00PM
Apopka Amphitheater
Apopka, FL
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A woman with red hair sings into a sparkly microphone while playing a pink guitar on stage with colorful lights.
Willow Avalon
Oct 9 • 9:00PM
Tuffy's Music Box
Sanford, FL
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Back view of a country singer with a cowboy hat and long hair on stage, facing a large, blurred audience.
Ward Davis
Aug 29 • 6:00PM
The Social - FL
Orlando, FL
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A man in a cowboy hat on stage with a microphone, facing a crowd.
Jake Worthington
Oct 1 • 8:00PM
Tuffy's Music Box
Sanford, FL
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Winter Park Country Schedule

2-23-25
Aug 18
Tue • 7:00 PM
Tue
Aug 18
7:00 PM
Royale Lynn
Conduit
Winter Park, FL
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2-23-25
Aug 20
Thu • 8:00 PM
Thu
Aug 20
8:00 PM
Drew Baldridge
Tuffy's Music Box
Sanford, FL
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2-23-25
Aug 29
Sat • 6:00 PM
Sat
Aug 29
6:00 PM
Ward Davis
The Social - FL
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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2-23-25
Sep 10
Thu • 8:00 PM
Thu
Sep 10
8:00 PM
The Mavericks
The Plaza Live
Orlando, FL
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2-23-25
Sep 18
Fri • 7:30 PM
Fri
Sep 18
7:30 PM
Clint Black
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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2-23-25
Sep 25
Fri • 7:30 PM
Fri
Sep 25
7:30 PM
Little Big Town
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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2-23-25
Oct 1
Thu • 8:00 PM
Thu
Oct 1
8:00 PM
Jake Worthington
Tuffy's Music Box
Sanford, FL
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2-23-25
Oct 3
Sat • TBD
Sat
Oct 3
TBD
Touch Grass Music Fest
Orlando Amphitheater at Central Florida Fairgrounds
Orlando, FL
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2-23-25
Oct 9
Fri • 9:00 PM
Fri
Oct 9
9:00 PM
Willow Avalon
Tuffy's Music Box
Sanford, FL
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2-23-25
Oct 14
Wed • 6:30 PM
Wed
Oct 14
6:30 PM
The Red Clay Strays, The Revivalists & Haley Reinhart
Kia Center
Orlando, FL
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2-23-25
Oct 31
Sat • 9:00 PM
Sat
Oct 31
9:00 PM
Nick Shoulders
Tuffy's Music Box
Sanford, FL
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2-23-25
Nov 7
Sat • 6:00 PM
Sat
Nov 7
6:00 PM
The Brook and The Bluff
The Social - FL
Orlando, FL
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2-23-25
Nov 9
Mon • 7:00 PM
Mon
Nov 9
7:00 PM
Yaelokre
The Beacham
Orlando, FL
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2-23-25
Nov 21
Sat • 6:00 PM
Sat
Nov 21
6:00 PM
Dylan Gossett, Buffalo Traffic Jam & The Jack Wharff Band
Apopka Amphitheater
Apopka, 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
Royale Lynn Aug 18 Conduit $70
Drew Baldridge Aug 20 Tuffy's Music Box $60
Ward Davis Aug 29 The Social - FL $93
Three On A String In Concert Sep 4 Sharon L. Morse Performing Arts Center $88
Charley Crockett Sep 9 Dr. Phillips Center - Walt Disney Theater $77
The Mavericks Sep 10 The Plaza Live $83
Ann Wilson Sep 12 Sharon L. Morse Performing Arts Center $124
Clint Black Sep 18 Dr. Phillips Center - Walt Disney Theater $140
Graham Barham Sep 24 Dirty Birds Tiki Bar & Grill $47
Little Big Town Sep 25 Dr. Phillips Center - Walt Disney Theater $132

Top Venues in Winter Park, FL

Modern building with curved glass facade illuminated by sunset light.
Kia Center
Orlando, FL
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Modern building with curved roof and large windows reflecting an orange sunset.
Dr. Phillips Center - Walt Disney Theater
Orlando, FL
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Aerial view of a modern business district with office buildings, parking lots, and a lake.
Funny Bone Comedy Club - Orlando
Orlando, FL
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A race track in front of stadium seating under a colorful sunset sky.
Daytona International Speedway
Daytona Beach, FL
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Rustic wooden building with colorful, illuminated windows and a covered entrance at dusk.
House Of Blues - Orlando
Orlando, FL
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Aerial view of a baseball field with green and red infield, surrounded by buildings, a parking lot, and a body of water.
Jackie Robinson Ballpark
Daytona Beach, FL
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Aerial view of a baseball stadium at dusk, with dramatic clouds and field lights illuminating the game.
Publix Field at Joker Marchant Stadium
Lakeland, FL
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A large, packed concert hall with a stage lit by blue spotlights and two large screens displaying abstract purple visuals.
Hard Rock Live - Orlando
Orlando, FL
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Modern building with a glass facade and a large roof overhang, with trees and flowers in the foreground.
Dr. Phillips Center - Steinmetz Hall
Orlando, FL
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Outdoor stage with a large arched canopy and white fabric panels, illuminated by warm sunlight.
Riverfront Park - Cocoa Village
Cocoa, FL
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All Venues Near Winter Park, FL