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Dating Events and Things to do in Winter Park, FL

Mike Posner At The Vanguard
Fri, Jul 3, 10:00 PM
Orlando · The Vanguard
Mike Posner At The Vanguard
Fri, Jul 3, 10:00 PM
Orlando · The Vanguard
Frank Ski and Friends Shuttle From Host Hotel To Cruise Port
Mon, Jun 8, 9:30 AM
Orlando · Marriott Orlando Airport Lakeside
Frank Ski and Friends Shuttle From Host Hotel To Cruise Port
Mon, Jun 8, 9:30 AM
Orlando · Marriott Orlando Airport Lakeside
The Renovation Project
Sat, Jun 13, 7:00 PM
Orlando · 771 S Kirkman Rd
The Renovation Project
Sat, Jun 13, 7:00 PM
Orlando · 771 S Kirkman Rd
BLACK GOLD ⭐️: Orlando's #1 Juneteenth R&B Experience ✨
Fri, Jun 19, 10:00 PM
Orlando · The Vanguard
BLACK GOLD ⭐️: Orlando's #1 Juneteenth R&B Experience ✨
Fri, Jun 19, 10:00 PM
Orlando · The Vanguard
Matuê At The Vanguard
Fri, Jul 31, 10:00 PM
Orlando · The Vanguard
Matuê At The Vanguard
Fri, Jul 31, 10:00 PM
Orlando · The Vanguard
Salute to Sisters in Service (Orlando)
Wed, Jun 17, 5:30 PM
Orlando · Dubsdread Event Center
Salute to Sisters in Service (Orlando)
Wed, Jun 17, 5:30 PM
Orlando · Dubsdread Event Center
Sales end soon
Gorgeous -Where Classics Play and Style Shines - 1st Friday - All Black
Friday at 6:00 PM
Orlando · Blue Martini Lounge Pointe Orlando
Sales end soon
Gorgeous -Where Classics Play and Style Shines - 1st Friday - All Black
Friday at 6:00 PM
Orlando · Blue Martini Lounge Pointe Orlando
LIVE AT THE BBQ
Sat, Jun 13, 5:00 PM
Orlando · The Nash Orlando
LIVE AT THE BBQ
Sat, Jun 13, 5:00 PM
Orlando · The Nash Orlando
WOO Welcome Kickoff Party - Friday Night June 12, 2026
Fri, Jun 12, 7:00 PM
Orlando · DoubleTree by Hilton Hotel at the Entrance to Universal Orlando
WOO Welcome Kickoff Party - Friday Night June 12, 2026
Fri, Jun 12, 7:00 PM
Orlando · DoubleTree by Hilton Hotel at the Entrance to Universal Orlando
3rd Annual "Blacker The Berry..."
Sat, Jun 27, 4:00 PM
Maitland · Venue on Lake Lily / Maitland Civic Center
3rd Annual "Blacker The Berry..."
Sat, Jun 27, 4:00 PM
Maitland · Venue on Lake Lily / Maitland Civic Center
Pride and Proud Pub Crawl
Sat, Jun 13, 6:00 PM
Orlando · Thornton Park
Pride and Proud Pub Crawl
Sat, Jun 13, 6:00 PM
Orlando · Thornton Park
OBL - Battle of the Cities - Standing 6
Fri, Jun 12, 6:00 PM
Orlando · Oak Ridge High School
OBL - Battle of the Cities - Standing 6
Fri, Jun 12, 6:00 PM
Orlando · Oak Ridge High School
Strong Not Silent 1 Year Anniversary
Sun, Jun 14, 3:00 PM
Orlando · 111 E Washington St
Strong Not Silent 1 Year Anniversary
Sun, Jun 14, 3:00 PM
Orlando · 111 E Washington St
Going fast
Kokedama Workshop
Sat, Jun 13, 10:00 AM
Orlando · Harry P. Leu Gardens
Going fast
Kokedama Workshop
Sat, Jun 13, 10:00 AM
Orlando · Harry P. Leu Gardens
Burlesque & Blues
Thu, Jun 18, 7:00 PM
Orlando · The Phoenix Jazz Club
Burlesque & Blues
Thu, Jun 18, 7:00 PM
Orlando · The Phoenix Jazz Club
Femme Forward: The Renaissance A Pride & Juneteenth celebration
Wed, Jun 17, 6:00 PM
Orlando · Noir Bar
Femme Forward: The Renaissance A Pride & Juneteenth celebration
Wed, Jun 17, 6:00 PM
Orlando · Noir Bar
Morgan Page @ CELINE ORLANDO (CLASSICS ONLY)
Fri, Jul 10, 10:00 PM
Orlando · Celine Orlando
Morgan Page @ CELINE ORLANDO (CLASSICS ONLY)
Fri, Jul 10, 10:00 PM
Orlando · Celine Orlando
R&B Wing Festival
Sat, Jul 25, 12:00 PM
Orlando · Festival Park
R&B Wing Festival
Sat, Jul 25, 12:00 PM
Orlando · Festival Park
*Sold Out* MASTERS OF THE UNIVERSE (HeMan Private Screening) Join Waitlist
Tue, Jun 9, 6:30 PM
Orlando · Cinemark Orlando and XD
*Sold Out* MASTERS OF THE UNIVERSE (HeMan Private Screening) Join Waitlist
Tue, Jun 9, 6:30 PM
Orlando · Cinemark Orlando and XD
FPRA Orlando & PRSA Orlando Media Mashup 2026
Fri, Jun 26, 8:00 AM
Sanford · Seminole State College
FPRA Orlando & PRSA Orlando Media Mashup 2026
Fri, Jun 26, 8:00 AM
Sanford · Seminole State College

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